[ CAS No. 79060-88-1 ] {[proInfo.proName]}

Name: 79060-88-1|Sodium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate|97%
Brand: Ambeed
SKU: A136880
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Quality Control of [ 79060-88-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 79060-88-1 ]

SDS Specification

Alternatived Products of [ 79060-88-1 ]

Product Details of [ 79060-88-1 ]

CAS No. :	79060-88-1	MDL No. :	MFCD00043323
Formula :	C₃₂H₁₂BF₂₄Na	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LTGMONZOZHXAHO-UHFFFAOYSA-N
M.W :	886.20	Pubchem ID :	23681909
Synonyms :

Calculated chemistry of [ 79060-88-1 ]

Physicochemical Properties

Num. heavy atoms :	58
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.25
Num. rotatable bonds :	12
Num. H-bond acceptors :	24.0
Num. H-bond donors :	0.0
Molar Refractivity :	150.07
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-1.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	14.17
Log Po/w (WLOGP) :	20.43
Log Po/w (MLOGP) :	11.02
Log Po/w (SILICOS-IT) :	13.7
Consensus Log Po/w :	11.86

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	4.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	-13.78
Solubility :	0.0 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (Ali) :	-14.26
Solubility :	0.0 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-16.38
Solubility :	0.0 mg/ml ; 4.17e-17 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	4.59

Safety of [ 79060-88-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 79060-88-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 79060-88-1 ]
Downstream synthetic route of [ 79060-88-1 ]

[ 79060-88-1 ] Synthesis Path-Upstream 1~5

1
[ 13755-29-8 ]
[ 328-70-1 ]
[ 79060-88-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With magnesium; ethylene dibromide In diethyl ether at 20℃; Inert atmosphere; Heating	A three-neck round bottom flask fitted with a reflux condenser was evacuated, flame dried and filledwith argon prior to use. 1.01 g (41.7 mmol) magnesium, 0.72 g (6.4 mmol, 1 eq) NaBF4 and diethylether (150 mL) were added. To start to reaction 1.07 g (0.49 ml, 5.7 mmol, 0.9 eq) dibromoethanewere added and the flask was heated for several minutes followed by the dropwise addition of 1.71 g(6.25 ml, 36 mmol) 3,5-bis(trifluoromethyl)bromobenzene diluted with diethyl ether (50 mL) over30 min. When the exothermic reaction slowed the reaction mixture was heated for additional 30 min.The solution was then stirred over night at room temperature. The reaction mixture was quenched bythe addition of 16 g Na2CO3 in distilled water (200 mL), stirred for 30 min and filtered. The aqueousphase was extracted three times with diethyl ether (50 mL), the combined organic phases were driedover sodium sulfate and charcoal followed by filtration. The solvent was removed and the remainingcrude product was dissolved in toluene (200 mL) to remove the water with a Dean Stark trap byazeotropic distillation. The solvent was removed, the product filtered, washed with dry toluene anddried under vacuo. The product was observed as colorless solid (4.65 g, 5.3 mmol, 82 percent).m.p. decomposition >290 °C.1H-NMR (300 MHz, DMSO-d6): δ = 7.67 (s, 4H, B-p-CH), 7.61 (s, 8H, B-o-CH) ppm.13C-NMR (75.5 MHz, DMSO-d6): δ = 161.0 (q, JB = 50 Hz, 4 Ci-B), 134.0 (s, 8 B-o-CH), 128.5 (qq,JF = 31 Hz, JB = 2.7 Hz, 8 Ci-CF3), 124.0 (q, JF = 272 Hz, CF3), 117.6 (m, 4 B-p-CH) ppm.19F-NMR (283 MHz, DMSO-d6): δ = -57.6 (CF3) ppm.Elemental analysis for C32H12BF24Na*1.8 H2O: calcd. C = 41.61 H = 1.70, found C = 41.57, H = 1.66.

Reference： [1] Inorganic Chemistry, 2014, vol. 54, # 1, p. 359 - 369
[2] Inorganic Chemistry, 2014, vol. 54, # 1, p. 359 - 369
[3] Tetrahedron Letters, 2016, vol. 57, # 31, p. 3453 - 3456
[4] Organic Syntheses, 2008, vol. 85, p. 248 - 266
[5] Journal of the American Chemical Society, 2001, vol. 123, # 44, p. 11020 - 11028
[6] Organometallics, 1992, vol. 11, p. 3920 - 3922
[7] Organometallics, 2005, vol. 24, # 14, p. 3579 - 3581
[8] Angewandte Chemie - International Edition, 2018, vol. 57, # 40, p. 13335 - 13338[9] Angew. Chem., 2018, vol. 130, p. 13519 - 13522,4

2
[ 328-70-1 ]
[ 497-19-8 ]
[ 79060-88-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: With magnesium; ethylene dibromide In diethyl ether at 20℃; Heating / reflux Stage #2: for 0.5 h;	f) Preparation of Sodium tetrakis [3,5-bis-(trifluoromethyl)-phenyl]-borate (as described by D. L. Reger, T. D. Wright, C. A. Little, J. J. S. Lamba, M. D. Smith in Inorg. Chem., 2001, 40, 3810-3814); Step f-1: A total of 3.49 g (31.7 mmol, 1 eq.) of sodium tetrafluoroborate, 4.98 g (205 mmol, 6.45 eq.) and 600 mL of anhydrous ether were charged in a 2 L 4 neck round bottom flask, equipped with overhead stirrer, addition funnel, thermocouple, condenser, nitrogen line and heating mantle. Dibromoethane (1 mL) was added, and the flask was gently heated to initiate the reaction. The heat was removed, and a solution of 50.94 g (174 mmol, 5.47 eq.) of 3,5-bis-(trifluoromethyl)-bromobenzene in 100 mL of ether was added dropwise within 30 min, which caused the solution to gently reflux. Once all bromide was added, the reaction was heated with a heating mantle to continue the reflux for an additional 1 hour. The heat than was removed, and the resulted mixture stirred overnight at room temperature. After this period of time, the reaction mixture was poured on a cold solution of sodium carbonate (77 g of Na₂CO₃in 950 mL of water) and stirred for 30 min. The top brown organic layer was separated, and the bottom milky aqueous layer was extracted with ether (2.x.300 mL). Combined organic phases were dried over sodium sulfate and stirred with 17 g of charcoal for 2 hours at room temperature. The mixture was filtered through the Celite pad, and the ether was removed on a rotovap to yield 32.4 g of brown semisolid. The obtained crude product was dissolved in 800 mL of benzene and water was removed with a Dean-Stark trap by azeotropic distillation for 3 hours. The solvent volume was reduced to about 200 mL and the residue was cooled on an ice bath to form a mixture of a solid and heavy brown oil. The heterogeneous mixture was filtered off, washed with benzene (3.x.50 mL) followed by hexane wash (1.x.100 mL). The isolated solid was dried under suction and nitrogen flow to yield 13.28 (47percent yield) of white solid with R_f=0.15 in EtOAc.

Reference： [1] Patent: US2007/27329, 2007, A1, . Location in patent: Page/Page column 7

3
[ 328-70-1 ]
[ 79060-88-1 ]

Reference： [1] Journal of the American Chemical Society, 2001, vol. 123, # 44, p. 11020 - 11028

4
[ 328-70-1 ]
[ 109-63-7 ]
[ 497-19-8 ]
[ 79060-88-1 ]

Reference： [1] Chemistry - A European Journal, 2016, vol. 22, # 14, p. 4738 - 4742

5
[ 160298-76-0 ]
[ 7647-14-5 ]
[ 79060-88-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 3, p. 776 - 781[2] Angew. Chem., 2017, vol. 129, p. 794 - 799,6

[ 79060-88-1 ] Synthesis Path-Downstream 1~88

1
[ 79060-88-1 ]
[ 65039-05-6 ]
1-butyl-3-methylimidazolium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2003,p. 2798 - 2811

2
[ 60-19-5 ]
[ 79060-88-1 ]
C₃₂H₁₂BF₂₄^(1-)*C₈H₁₁NO*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 815 - 824

3
2-[1-(2,4,6-trimethylphenylimino)ethyl]-6-[1-(4-eicosanoxy-3,5-diphenylphenylimino)ethyl]pyridine cobalt[II] dichloride complex [ No CAS ]
[ 79060-88-1 ]
2-[1-(2,4,6-trimethylphenylimino)ethyl]-6-[1-(4-eicosanoxy-3,5-diphenylphenylimino)ethyl]pyridine cobalt[II] chloride tetrakis[3,5-bis(trifluoromethyl)phenyl]borate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In toluene; at 20℃; for 1h;	In an inert atmosphere a 313 mg (0.353 mmol) of sodium tetrakis [3,5-bis (trifluoromethyl) phenyl] borate (ABCR GmbH & Co, Karlsruhe, Germany) was added to a solution of 330 mg (0.353 mmol) cobalt complex F in 20 ml toluene. The solution was stirred for 1 hour at room temperature. After removing the precipitate by centrifugation, the solvent was removed in vacuo. The resulting oil was washed three times with pentane. After drying in vacuo, the product was isolated as a yellowish solid (560 mg,90%). Its solubility in toluene or benzene-D6 is estimated at ca. 10 mg/ml at20 C.

Reference： [1]Patent: WO2005/90371,2005,A1 .Location in patent: Page/Page column 65

4
[ 328-70-1 ]
[ 497-19-8 ]
[ 79060-88-1 ]

Yield	Reaction Conditions	Operation in experiment
47%		f) Preparation of Sodium tetrakis [3,5-bis-(trifluoromethyl)-phenyl]-borate (as described by D. L. Reger, T. D. Wright, C. A. Little, J. J. S. Lamba, M. D. Smith in Inorg. Chem., 2001, 40, 3810-3814); Step f-1: A total of 3.49 g (31.7 mmol, 1 eq.) of sodium tetrafluoroborate, 4.98 g (205 mmol, 6.45 eq.) and 600 mL of anhydrous ether were charged in a 2 L 4 neck round bottom flask, equipped with overhead stirrer, addition funnel, thermocouple, condenser, nitrogen line and heating mantle. Dibromoethane (1 mL) was added, and the flask was gently heated to initiate the reaction. The heat was removed, and a solution of 50.94 g (174 mmol, 5.47 eq.) of 3,5-bis-(trifluoromethyl)-bromobenzene in 100 mL of ether was added dropwise within 30 min, which caused the solution to gently reflux. Once all bromide was added, the reaction was heated with a heating mantle to continue the reflux for an additional 1 hour. The heat than was removed, and the resulted mixture stirred overnight at room temperature. After this period of time, the reaction mixture was poured on a cold solution of sodium carbonate (77 g of Na2CO3 in 950 mL of water) and stirred for 30 min. The top brown organic layer was separated, and the bottom milky aqueous layer was extracted with ether (2×300 mL). Combined organic phases were dried over sodium sulfate and stirred with 17 g of charcoal for 2 hours at room temperature. The mixture was filtered through the Celite pad, and the ether was removed on a rotovap to yield 32.4 g of brown semisolid. The obtained crude product was dissolved in 800 mL of benzene and water was removed with a Dean-Stark trap by azeotropic distillation for 3 hours. The solvent volume was reduced to about 200 mL and the residue was cooled on an ice bath to form a mixture of a solid and heavy brown oil. The heterogeneous mixture was filtered off, washed with benzene (3×50 mL) followed by hexane wash (1×100 mL). The isolated solid was dried under suction and nitrogen flow to yield 13.28 (47% yield) of white solid with Rf=0.15 in EtOAc.

Reference： [1]Patent: US2007/27329,2007,A1 .Location in patent: Page/Page column 7

5
[ 13755-29-8 ]
[ 328-70-1 ]
[ 79060-88-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With magnesium; ethylene dibromide; In diethyl ether; at 20℃;Inert atmosphere; Heating;	A three-neck round bottom flask fitted with a reflux condenser was evacuated, flame dried and filledwith argon prior to use. 1.01 g (41.7 mmol) magnesium, 0.72 g (6.4 mmol, 1 eq) NaBF4 and diethylether (150 mL) were added. To start to reaction 1.07 g (0.49 ml, 5.7 mmol, 0.9 eq) dibromoethanewere added and the flask was heated for several minutes followed by the dropwise addition of 1.71 g(6.25 ml, 36 mmol) 3,5-bis(trifluoromethyl)bromobenzene diluted with diethyl ether (50 mL) over30 min. When the exothermic reaction slowed the reaction mixture was heated for additional 30 min.The solution was then stirred over night at room temperature. The reaction mixture was quenched bythe addition of 16 g Na2CO3 in distilled water (200 mL), stirred for 30 min and filtered. The aqueousphase was extracted three times with diethyl ether (50 mL), the combined organic phases were driedover sodium sulfate and charcoal followed by filtration. The solvent was removed and the remainingcrude product was dissolved in toluene (200 mL) to remove the water with a Dean Stark trap byazeotropic distillation. The solvent was removed, the product filtered, washed with dry toluene anddried under vacuo. The product was observed as colorless solid (4.65 g, 5.3 mmol, 82 %).m.p. decomposition >290 C.1H-NMR (300 MHz, DMSO-d6): delta = 7.67 (s, 4H, B-p-CH), 7.61 (s, 8H, B-o-CH) ppm.13C-NMR (75.5 MHz, DMSO-d6): delta = 161.0 (q, JB = 50 Hz, 4 Ci-B), 134.0 (s, 8 B-o-CH), 128.5 (qq,JF = 31 Hz, JB = 2.7 Hz, 8 Ci-CF3), 124.0 (q, JF = 272 Hz, CF3), 117.6 (m, 4 B-p-CH) ppm.19F-NMR (283 MHz, DMSO-d6): delta = -57.6 (CF3) ppm.Elemental analysis for C32H12BF24Na*1.8 H2O: calcd. C = 41.61 H = 1.70, found C = 41.57, H = 1.66.

Reference： [1]Inorganic Chemistry,2014,vol. 54,p. 359 - 369
[2]Inorganic Chemistry,2014,vol. 54,p. 359 - 369
[3]Tetrahedron Letters,2016,vol. 57,p. 3453 - 3456
[4]Organic Syntheses,2008,vol. 85,p. 248 - 266
[5]Journal of the American Chemical Society,2001,vol. 123,p. 11020 - 11028
[6]Organometallics,1992,vol. 11,p. 3920 - 3922
[7]Organometallics,2005,vol. 24,p. 3579 - 3581
[8]Angewandte Chemie - International Edition,2018,vol. 57,p. 13335 - 13338
Angew. Chem.,2018,vol. 130,p. 13519 - 13522,4
[9]Organic Letters,2020

6
[ 102-54-5 ]
[ 79060-88-1 ]
[ 156301-37-0 ]

Yield	Reaction Conditions	Operation in experiment
61.3%		In the similar apparatus to that used in Example 1, 0.5g of commercially available ferrocene was added to 10g of conc. sulfuric acid. The resulting solution was stirred at room temperature for 5 hours, and then 100ml of pure water was added thereto. The flask containing the solution was cooled, and the solution was filtered with PTFE filter paper. The filtrate was transferred to a beaker made of Pyrex glass (capacity: 300ml), and ethanol solution (7ml) containing 2.48g of tetrakis[3,5-bis(trifluoromethyl)phenyl] borate sodium salt (CAS 79060-88-1) was added. Blue colored crystal precipitated. The precipitate was filtered, washed with pure water, dried by evaporator, washed with toluene, and dried again by evaporator. 1.73g of ferrocenium/tetrakis[3,5-bis(trifluoromethyl)phenyl] borate was obtained (yield 61.3%).

Reference： [1]Journal of Organometallic Chemistry,2000,vol. 616,p. 54 - 66
[2]Organometallics,1998,vol. 17,p. 51 - 58
[3]Patent: EP1153905,2004,B1 .Location in patent: Page 11

7
[(2,6-iPrC₆H₃NC(Me)C(Me)N-2,6-iPrC₆H₃)Pd(CH₃)(Cl)] [ No CAS ]
[ 27126-93-8 ]
[ 79060-88-1 ]
[ 201007-19-4 ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 888 - 899

8
silver nitrate [ No CAS ]
[ 79060-88-1 ]
[ 160298-76-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	In diethyl ether; water; for 0.0833333h;	10 mL of water in which silver nitrate (254 mg, 1.5 mmol) was dissolved and dissolved in NaBArF (886 mg, 1 mmol)The ether (20 mL) was placed in a separatory funnel wrapped with aluminum foil and shaken vigorously for 5 minutes.The organic layer was separated and evaporated to give AgBArF.It was a white solid (920 mg, 95% yield).

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 8509 - 8515
[2]Patent: CN109535018,2019,A .Location in patent: Paragraph 0088; 0091
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 776 - 781
Angew. Chem.,2017,vol. 129,p. 794 - 799,6
[4]Journal of the American Chemical Society,1996,vol. 118,p. 5502 - 5503
[5]Journal of the American Chemical Society,2019,vol. 141,p. 8868 - 8876

9
[ 366-18-7 ]
[ 14871-92-2 ]
[ 79060-88-1 ]
bis(2,2'-bipyridine)palladium(II) bis(tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 664,p. 77 - 84
[2]Journal of Organometallic Chemistry,2004,vol. 689,p. 1521 - 1529

10
[ 709047-65-4 ]
[ 79060-88-1 ]
[ 56100-20-0 ]
bis(5-methyl-2,2'-bipyridine)palladium(II) bis(tetrakis[3,5-bis(trifluoromethyl)phenyl]borate) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2004,vol. 689,p. 1521 - 1529

11
[ 185406-04-6 ]
[ 27126-93-8 ]
[ 79060-88-1 ]
[ 851539-79-2 ]

Reference： [1]Organometallics,2004,vol. 23,p. 6099 - 6107

12
{(bis(2,6-diisopropylphenylimino)acenaphthene)(chloro)(methyl)palladium} [ No CAS ]
[ 27126-93-8 ]
[ 79060-88-1 ]
[ 825615-73-4 ]

Reference： [1]Organometallics,2004,vol. 23,p. 6099 - 6107

13
[ 179268-55-4 ]
[ 79060-88-1 ]
[ 13406-29-6 ]
[ 849519-15-9 ]

Reference： [1]Inorganic Chemistry,2005,vol. 44,p. 1248 - 1262

14
[ 179268-55-4 ]
[ 79060-88-1 ]
[ 6372-42-5 ]
[ 849519-31-9 ]

Reference： [1]Inorganic Chemistry,2005,vol. 44,p. 1248 - 1262

15
chloro(1,5-cyclooctadiene)rhodium(I) dimer [ No CAS ]
[ 131833-93-7 ]
[ 79060-88-1 ]
[Rh(1,5-COD)((S,S)-2,2'-isopropylidene-bis(4-tert-butyl-2-oxazoline))](BAr(F)) [ No CAS ]

Reference： [1]Organometallics,2006,vol. 25,p. 1749 - 1754

16
[ 578743-87-0 ]
[ 79060-88-1 ]
[ 75-05-8 ]
[(1,3-bis(diisopropylphenyl)imidazol-2-ylidene)Cu(CH₃CN)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate] [ No CAS ]

Reference： [1]Organometallics,2006,vol. 25,p. 2237 - 2241

17
(1,10-phenanthroline)methylchloropalladium(II) [ No CAS ]
[ 27126-93-8 ]
[ 79060-88-1 ]
[ 175084-15-8 ]

Reference： [1]Organometallics,2007,vol. 26,p. 1261 - 1269

18
[ 102-06-7 ]
[ 79060-88-1 ]
N,N’-diphenylguanidinium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 9228 - 9229
[2]Organic Letters,2009,vol. 11,p. 621 - 624
[3]Angewandte Chemie - International Edition,2016,vol. 55,p. 539 - 544
Angew. Chem.,2016,vol. 128,p. 549 - 554,6

19
[ 1092516-26-1 ]
[ 79060-88-1 ]
2‐(((1S,2R)‐2‐hydroxy‐2,3‐dihydro‐1H‐inden‐1‐yl)carbamothioyl)quinolin‐1‐ium tetrakis[3,5‐bis(trifluoromethyl)phenyl]borate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 16464 - 16465

20
[ 936-49-2 ]
[ 79060-88-1 ]
C₉H₁₀N₂*C₃₂H₁₂BF₂₄^(1-)*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organic Letters,2009,vol. 11,p. 621 - 624

21
chloromethyl(1,5-cyclooctadiene)palladium(II) [ No CAS ]
(CH₃)2C₅₂H₂₆N₂F₈ [ No CAS ]
[ 27126-93-8 ]
[ 79060-88-1 ]
[ 1175097-12-7 ]

Reference： [1]Organometallics,2009,vol. 28,p. 4452 - 4463

22
[ 65554-34-9 ]
[ 79060-88-1 ]
1,2,4,1',2',4'-hexamethyl ferrocenium/tetrakis[3,5-bis(trifluoromethyl)phenyl]borate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.5%		In the similar apparatus to that used in Example 1, 0.5g of 1,2,4,1',2',4'-hexamethyl ferrocene was added to 10g of conc. sulfuric acid. The resulting solution was stirred at room temperature for 16 hours, and then 100ml of pure water was added thereto. The flask containing the solution was cooled, and the solution was filtered with PTFE filter paper. The filtrate was heated to 60C by water bath with stirring, and ethanol solution (7ml) containing 1.71g of tetrakis[3,5-bis(trifluoromethyl)phenyl] borate sodium salt was added. Blue-green colored crystal precipitated. The precipitate was filtered, washed with pure water, dried by evaporator, washed with toluene, and dried again by evaporator. 1.08g of 1,2,4,1',2',4'-hexamethyl ferrocenium/tetrakis[3,5-bis(trifluoromethyl)phenyl] borate was obtained (yield 51.5%). The identification was carried out by 1H-NMR analysis similarly to the Example 2, and the following data was obtained.1HNMR [25C, deuterated acetone, chemical shift of peak(ppm)]: 17.1 (methyl); 7.58, 7.50 (phenyl)

Reference： [1]Patent: EP1153905,2004,B1 .Location in patent: Page 11-12

23
[ 12156-05-7 ]
[ 79060-88-1 ]
(2-ferrocenylethyl)ferrocenium/tetrakis[3,5-bis(trifluoromethyl)phenyl]borate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.2%		In the similar apparatus to that used in Example 1, 1g of commercially available 1,2-diferrocenyl ethane (CAS 12156-05-7) was added to 15g of conc. sulfuric acid. The resulting solution was stirred at room temperature for 16 hours, and then 100ml of pure water was added thereto. The flask containing the solution was cooled, and the solution was filtered with PTFE filter paper. The filtrate was heated to 70C by water bath with stirring, and 4.86g of tetrakis[3,5-bis(trifluoromethyl)phenyl] borate sodium salt was added. Blue-green colored crystal precipitated. After the flask was left still for 1 hour under stirring, the precipitate was filtered, washed with pure water, dried by evaporator, washed with toluene, and dried again by evaporator. 3.16g of (2-ferrocenylethyl) ferrocenium/tetrakis[3,5-bis(trifluoromethyl)phenyl] borate was obtained (yield 59.2%).

Reference： [1]Patent: EP1153905,2004,B1 .Location in patent: Page 13

24
C₂₇H₃₇N₂OP [ No CAS ]
[ 79060-88-1 ]
C₈H₁₂*C₂₇H₃₇N₂OP*C₃₂H₁₂BF₂₄^(1-)*Ir⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		[Ir (COD) CI] 2 (27 mg, 0.039 mmol) is placed in a reaction vessel together with DICHLOROMETHANE (0.5 ML). The phosphinite C1 (32 mg, 0.071 MMOL, dissolved in DICHLOROMETHANE, 4.0 ML) is added dropwise to the solution and the mixture is subsequently heated to 45C. After 2 h, the solution is admixed with sodium tetra (bistrifluoro- methyl) phenyl) borate (NaBArF) (74 mg, 0. 078 MMOL) and water. After phase separation and extraction of the aqueous phase with DICHLOROMETHANE (10 ml), the combined organic extracts are dried over MGS04 and the DICHLOROMETHANE is subsequently removed on a rotary evaporator. The orange foam formed is purified by column chromatography on silica gel (DICHLOROMETHANE). This gives the complex D1 as an orange solid (105 mg, 91%). 'H-NMR (500.1 MHz, CDC13, 295 K): # = -0. 04 (d, J = 6. 5 Hz, 3H, CH (CH3) 2), 0.74 (d, J = 7.0 Hz, 3H, CH (CH3) 2), 1.05 (m, 1H, CH2), 1.23 (m, 2H, CH2), 1.40-1. 70 (m, 5H, COD and Cy), 1.70-1. 80 (m, 5H, COD and Cy), 1.80 (m, 1H, CH (CH3) 2), 1.90 (d, J = 2.0 Hz, 3H, CH3), 1.94 (m, 1H, CH2), 2.10 (m, 1H, CH2), 2.34 (m, 1H, CH2), 2.34 (s, 3H, CH3), 2.41 (m, 1H, CH2), 2.55 (m, 2H, CH2), 3.23 (m, 1H, CH, COD), 3.39 (dd, J= 11. 0,5. 0 Hz, 1H, CH2, Im), 3.46 (t, J = 11.5 Hz, 1 H, CH2, Im), 3.64 (m, 1H, CH, Im), 3.85 (m, 1H, CH, Cy), 5.04 (m, 1H, CH, COD), 5.20 (m, 1 H, CH, COD), 7. 11 (m, 2H, Ar-H), 7.41-7. 47 (m, 6H, Ar-H), 7.52 (s br, 3H, BArF), 7.54 (m, 1 H, Ar-H), 7.71 (s, 8H, BArF), 7.83 (2H, N-Ar-H) ppm. 31P-NMR (161.9 MHz, CDCI3, 300 K): # = 94. 7 ppm.

Reference： [1]Patent: WO2005/21562,2005,A2 .Location in patent: Page/Page column 49-50

25
[ 108-48-5 ]
[ 79060-88-1 ]
[ 585524-03-4 ]

Reference： [1]Chemical Communications,2009,p. 5121 - 5123
[2]Journal of the American Chemical Society,2015,vol. 137,p. 13768 - 13771
[3]Journal of the American Chemical Society,2017,vol. 139,p. 13126 - 13140

26
[ 110-86-1 ]
Noyori's catalyst [ No CAS ]
[ 79060-88-1 ]
[Ru(p-cymene)(R,R-TsDPEN)(pyridine)]B[3,5-(CF₃)2C₆H₃]4 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		(k) Ru(p-cymene) (R, R- TsDPEN) (pyridine)]B[3, 5-(CFs)2C6H3)U In an Ar filled flask, 0.080 g (0.13 mmol) of [RuCI(p- cymene)(RR-TsDPEN)], 0.114 g (0.13 mmol) of NaB[3,5-(CF3)2C6H3)]4 and 0.025 g Of AgBF4 (0.13 mmol) were combined. CH2CI2 (5 ml_) was added and the resulting brown-purple mixture was left to stir at ambient temperature overnight. After 16 hours, the suspension was filtered through a 0.45 mm PTFE syringe filter and 10 ml_ (0.13 mmol) of pyridine was added. The resulting brown solution was concentrated to dryness leaving a brown residue. Yield: 0.15O g (72 %). 1H NMR and 19F(1HJ NMR (ppm, CDCI3) showed the product was obtained.

Reference： [1]Patent: WO2009/132443,2009,A1 .Location in patent: Page/Page column 24; 25

27
Noyori's catalyst [ No CAS ]
[ 79060-88-1 ]
[Ru(p-cymene)(R,R-TsDPEN)]B[3,5-(CF₃)2C₆H₃]4 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With silver tetrafluoroborate; In dichloromethane; at 20℃; for 21h;Inert atmosphere;	In an Ar filled flask, 0.08 g (0.13 mmol) of [RuCI(p-cymene)(R,R-TsDPEN)] and 0.111 g (0.13 mmol) of NaB[3,5-(CF3)2C6H3)]4 and 0.025 g (0.13 mmol) of AgBF4 were combined. CH2CI2 (5 ml_) was added and the resulting brown purple mixture was left to stir at ambient temperature overnight. After 21 hours, the suspension was filtered through a 0.45 mm PTFE syringe filter. The purple filtrate was concentrated to dryness leaving a purple residue. Yield: 0.145 g (70 %). 1H and 19F(1HJ NMR (ppm, CDCI3) showed the product was obtained.

Reference： [1]Patent: WO2009/132443,2009,A1 .Location in patent: Page/Page column 21

28
[ 61-76-7 ]
[ 79060-88-1 ]
C₉H₁₃NO₂*C₃₂H₁₂BF₂₄^(1-)*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 16896 - 16904

29
[ 96-69-5 ]
bis-allylnickel chloride [ No CAS ]
[ 79060-88-1 ]
[ 1220750-96-8 ]

Reference： [1]Journal of Organometallic Chemistry,2010,vol. 695,p. 673 - 679

30
[ 70477-56-4 ]
[ 34946-82-2 ]
[ 79060-88-1 ]
[Cu(1,3,5-tris(thiocyanatomethyl)mesitylene)]2[B(C₆H₃(CF₃)2)4]2 [ No CAS ]

Reference： [1]Inorganic Chemistry,2010,vol. 49,p. 6974 - 6985

31
[ 12112-67-3 ]
C₃₇H₃₁FeN₂P [ No CAS ]
[ 79060-88-1 ]
C₃₂H₁₂BF₂₄^(1-)*C₄₅H₄₃FeIrN₂P⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		Cati: In a previously dried Schlenk tube, Lig-5 (250 mg, 0.427 mmol) and [Ir(COD)CI]2 (149 mg, 0.222 mmol, 0.52 eq) were dissolved in dry CH2CI2 (6 mL) under nitrogen and the resulting solution was stirred at 50 0C for 1 h. After cooling to room temperature, sodium tetrakis[3,5-bis(trif I uorom ethyl )phenyl] borate (567 mg, 0.640 mmol, 1.5 eq) was added, followed by 6 mL of water and the resulting two-phase mixture was stirred vigorously for 15 min. The layers were separated, the aqueous phase extracted with CH2CI2 and the combined organic extracts evaporated under vacuum. The crude obtained was purified by flash column chromatography using hexane/CH2CI2 1/1 to afford Cati (650 mg, 0.371 , 87 % yield) as an orange solid.1H-NMR (CDCI3, 400 MHz) delta = 1.28 (m, 2H), 1.55 (m, 1 H), 2.02 (m, 3H), 2.29 (m, 1 H), 2.41 (m, 1 H), 2.73 (m, 1 H), 3.14 (m, 1 H), 4.43 (d, J = 4.0 Hz, 1 H), 4.60 (s, 1 H), 4.63 (s, 5H), 4.70 (m, 2H), 4.81 (d, J = 5.2 Hz, 1 H), 4.86 (t, J = 2.4 Hz, 1 H), 4.98 (s, 1 H), 5.95 (s, 1 H), 6.54 (d, J = 7.2 Hz, 2H), 7.07 (t, J = 7.2 Hz, 2H), 7.20 (m, 4H), 7.39 (m, 15H), 7.51 (m, 1 H), 7.63 (s, 9H) ppm. 31P-NMR (CDCI3, 162 MHz) delta = 9.42 ppm. HRMS (+ESI) calcd for C45H43FeIrN2P: 891.2107, found: 891.2137.

Reference： [1]Patent: WO2010/146172,2010,A2 .Location in patent: Page/Page column 52

32
chlorobis(cyclooctene)rhodium(I) dimer [ No CAS ]
[ 79060-88-1 ]
[ 247940-06-3 ]
[ 1287211-73-7 ]

Reference： [1]Organometallics,2011,vol. 30,p. 2105 - 2116

33
[ 64536-78-3 ]
[ 79060-88-1 ]
[ 900161-50-4 ]

Reference： [1]Canadian Journal of Chemistry,2011,vol. 89,p. 1457 - 1468

34
[ 388110-78-9 ]
[ 71071-46-0 ]
[ 79060-88-1 ]
[Pd(dimethyl-2,2'-bipyridine-4,4'-dicarboxylate)2][B(3,5-C₆H₃(CF₃)2)4]2 [ No CAS ]

Reference： [1]Organometallics,2011,vol. 30,p. 6572 - 6586

35
[ 12112-67-3 ]
[ 1251831-99-8 ]
[ 79060-88-1 ]
[ 1251832-10-6 ]

Yield	Reaction Conditions	Operation in experiment
88%		Iridium Complex of Ligand In:In a Schlenk tube under an argon atmosphere, a mixture of ligand (Sp)-1-[(1R)-(1-(5,6-dimethoxy-3H-isobenzofuran-1-ylideneamino)-ethyl)]-2-(diphenyl phosphino)-ferrocene (In) (100 mg, 0.170 mmol) and [Ir(COD)Cl]2 (57 mg, 0.0848 mmol) in dry CH2Cl2 (5 mL) was refluxed and stirred during 2 h. After cooling down to room temperature, NaBARF (225.5 mg, 0.254 mmol) was added to the solution and stirred for 5 min. Then, H2O (5 mL) is added, and the mixture was stirred vigorously for 20 min. The organic layer was seperated, and the aqueous phase was extracted with CH2Cl2 (2×5 mL). The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash chromatography over silica gel (pentane/CH2Cl2, 50/50) resulted in an orange foaming solid, 261.1 mg (88%). 31P-NMR (121.4 MHz, CDCl3): +6.8 ppm. IR (HATR): 2890, 1610, 1498, 1461, 1353, 1296, 1273, 1228, 1118, 1081, 1059, 1032, 1001, 886, 839, 744, 712, 682, 669 cm-1. ES-MS: 890.1 [M-BARF]+

Reference： [1]Patent: US2012/77989,2012,A1 .Location in patent: Page/Page column 18

36
[ 12112-67-3 ]
[ 1251832-00-4 ]
[ 79060-88-1 ]
[ 1251832-12-8 ]

Yield	Reaction Conditions	Operation in experiment
91%		Iridium complex of ligand Io In a Schlenk tube under an argon atmosphere, a mixture of ligand (Sp)-1-[(1R)-(1-(6-methyl-3H-isobenzofuran-1-ylideneamino)-ethyl)]-2-(diphenylphosphino)-ferrocene (Is) (94.7 mg, 0.174 mmol) and [Ir(COD)Cl]2 (62.3 mg, 0.0928 mmol) in dry CH2Cl2 (5 mL) was refluxed and stirred during 2 h. After cooling down to room temperature, NaBARF (248.5 mg, 0.280 mmol) was added to the solution and stirred for 5 min. Then, H2O (5 mL) was added, and the mixture was stirred vigorously for 20 min. The organic layer was seperated, and the aqueous phase is was extracted with CH2Cl2 (2×5 mL). The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash chromatography over silica gel (pentane/CH2Cl2, 50/50) resulted in an orange foaming solid, 269 mg (91%). 31P-NMR (121.4 MHz, CDCl3): 7.2 ppm. IR (HATR): 2892, 1627, 1437, 1353, 1273, 1158, 1117, 1061, 1032, 1001, 931, 886, 839, 820, 744, 712, 694, 682, 670 cm-1. ES-MS: 844.1 [M-BARF]+

Reference： [1]Patent: US2012/77989,2012,A1 .Location in patent: Page/Page column 18

37
BF₄^(1-)*C₇₈H₁₀₃O₄S⁽¹⁺⁾ [ No CAS ]
[ 63857-00-1 ]
[ 79060-88-1 ]
C₃₂H₁₂BF₂₄^(1-)*C₁₆₄H₂₁₀ClO₈S₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry of Materials,2012,vol. 24,p. 1606 - 1618

38
[ 4328-13-6 ]
[ 79060-88-1 ]
C₃₂H₁₂BF₂₄^(1-)*C₂₄H₅₂N⁽¹⁺⁾ [ No CAS ]

Reference： [1]Langmuir,2013,vol. 29,p. 4204 - 4213

39
[ 14866-33-2 ]
[ 79060-88-1 ]
tetraoctylammonium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate [ No CAS ]

Reference： [1]Langmuir,2013,vol. 29,p. 4204 - 4213

40
[ 6287-40-7 ]
[ 79060-88-1 ]
[ 1226878-18-7 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 7627 - 7638

41
[ 188860-22-2 ]
[ 75-09-2 ]
[ 39775-31-0 ]
[ 79060-88-1 ]
C₂₈H₂₄N₄O₈Pd⁽²⁺⁾*2C₃₂H₁₂BF₂₄^(1-)*1.5CH₂Cl₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	at 45℃; for 3h;	General procedure: To a suspension of [PdCl2(L1)] (35 mg, 0.031 mmol) in 10 mL of dichloromethane, a solution of L1 (32 mg, 0.034 mmol) and sodium tetrakis 3,5-(trifluoromethyl)phenyl borate (57 mg,0.064 mmol) in 5 mL of dichloromethane were added slowly. The mixture was heated for 3 h at 45 C. The product was filtered offover Celite and the solvent was removed under reduced pressure.The product was obtained as an oil and triturate with pentane to form a brown solid.

Reference： [1]Inorganica Chimica Acta,2014,vol. 409,p. 285 - 295

42
bis[2-(trifluoromethyl)propyl]-2,2'-bipyridine-3,3'-dicarboxylate [ No CAS ]
C₁₈H₈Cl₂F₁₂N₂O₄Pd [ No CAS ]
[ 79060-88-1 ]
[ 109-66-0 ]
C₃₆H₁₆F₂₄N₄O₈Pd⁽²⁺⁾*2C₃₂H₁₂BF₂₄^(1-)*3C₅H₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%		General procedure: To a suspension of [PdCl2(L1)] (35 mg, 0.031 mmol) in 10 mL of dichloromethane, a solution of L1 (32 mg, 0.034 mmol) and sodium tetrakis 3,5-(trifluoromethyl)phenyl borate (57 mg,0.064 mmol) in 5 mL of dichloromethane were added slowly. The mixture was heated for 3 h at 45 C. The product was filtered offover Celite and the solvent was removed under reduced pressure.The product was obtained as an oil and triturate with pentane toform a brown solid.

Reference： [1]Inorganica Chimica Acta,2014,vol. 409,p. 285 - 295

43
[ 95408-45-0 ]
[ 79060-88-1 ]
[Pd(1,1'-bis(di-tert-butylphosphino)ferrocene)Cl][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate] [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 5966 - 5979

44
[ 72287-26-4 ]
[ 79060-88-1 ]
[Pd(1,1'-bis(diphenylphosphino)ferrocene)(μ-Cl)]₂[tetrakis(3,5-bis(trifluoromethyl)phenyl)borate]₂ [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 5966 - 5979

45
[ 917511-90-1 ]
[ 79060-88-1 ]
[Pd(dcpf)(μ-Cl)]₂[tetrakis(3,5-bis(trifluoromethyl)phenyl)borate]₂ [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 5966 - 5979

46
[ 945491-51-0 ]
[ 27126-93-8 ]
[ 79060-88-1 ]
[Ir(η⁵-pentamethylcyclopentadienyl)(2-phenylene-κC1′-pyridine-κN)(3,5-bis(trifluoromethyl)-benzonitrile)][tetrakis[3,5-bis(trifluoromethyl)phenyl]borate] [ No CAS ]

Reference： [1]Inorganic Chemistry,2013,vol. 52,p. 11351 - 11360

47
[ 644-98-4 ]
[ 12112-67-3 ]
[ 79060-88-1 ]
[ 2622-14-2 ]
C₃₂H₁₂BF₂₄^(1-)*C₃₄H₅₆IrNP⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 6170 - 6173

48
[ 854391-95-0 ]
[ 79060-88-1 ]
C₁₆H₁₉NO₂*C₃₂H₁₂BF₂₄^(1-)*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 9917 - 9920

49
[(bis(dicyclohexylphosphino)ethane)nickel(propanoate-3-yl)] [ No CAS ]
[ 79060-88-1 ]
[(dcpe)Ni(kC,kO-CH₂CH₂COONa)][BAr₄^F] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In tetrahydrofuran; at 20℃; for 0.166667h;	A 20 mL scintillation vial was charged with 0.058 g (0.105 mmol) of 1 -ylactone, 0.099 g (0.1 1 2 mmol) of NaBAr4F, and approximately 3 mL of THF. After the mixture was stirred at ambient temperature for 1 0 minutes, the volatiles were removed in vacuo. The residue was washed with benzene and extracted with diethyl ether. Concentrating the solution, layering with pentane and chilling to -35 C afforded 0.145 g (96%) of 1 -vlactoneNa as orange crystals. Anal. Calcd for C6i H64BF24NaNi02P2: C, 50.89; H, 4.48. Found: C, 50.94; H, 4.71 . 1 H NMR (C6D5Br) : delta 0.82 (m, 2H, Ni-a-CH2), 1 .1 -1 .72 (44H, PCy2), 1 .94, 2.02 (m, 4H, PCH2CH2P), 2.31 (m, 2H, Ni- beta -CH2), 7.63 (s, 4H, BAr4F), 8.1 8 (s, 8H, BAr4F). 13C{1 H} NMR (C6D5Br) : delta 1 2.1 1 (Ni- a -CH2), 25.31 -25.78, 26.57-26.93, 28.60, 28.88, 29.37, 29.80 (PCy2-CH2), 33.49, 35.43 (PCy2-CH), 36.67 (Nu-beta-OmicronEta2), 1 1 7.48, 1 23.26, 134.86, 1 62.1 1 (BAr4F), one aryl and one quaternary signal not located. 31 P{1 H} NMR (C6D5Br): delta 60.62 (s, 1 P, PCy2), 70.93 (s, 1 P, PCy2). 19F NMR (C6D5Br) : -62.95 (s).

Reference： [1]Patent: WO2014/130410,2014,A1 .Location in patent: Page/Page column 23

50
(dcpm)Ni(kC,kO-CH₂CH₂CO₂) [ No CAS ]
[ 79060-88-1 ]
[(dcpm)Ni(kC,kO-CH₂CH₂COONa)][BAr₄^F] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	In tetrahydrofuran; at 20℃; for 0.166667h;	A 20 mL scintillation vial was charged with 0.040 g (0.074 mmol) of 2-Ylactone, 0.073 g (0.082 mmol) of NaBAr4F, and approximately 3 mL of THF. After the mixture was stirred at ambient temperature for 10 minutes, the volatiles were removed in vacuo. The residue was washed with benzene and extracted with diethyl ether. Layering the concentrated diethyl ether solution with pentane and chilling at -35 C afforded 0.103 g (97%) of 2-ylactoneNa as orange crystals. 1 H NMR (C6D5Br): delta 0.71 (m, 2H, Ni-a-CH2), 1 .04-1 .94 (m, 44H, PCy2), 2.01 (m, 2H, Nu-beta-OmicronEta2), 2.1 3 (m, 2H, PCH2P) 7.63 (s, 4H, BAr4F), 8.18 (s, 8H, BAr4F). 13C{1 H} NMR (C6D5Br) : 5 7.42 (Ni-a-CH2), 25.1 3, 25.63, 26.31 , 26.66-26.93, 28.28, 29.26, 29.34 (PCy2-CH2), 29.09 (PCH2P), 34.28, 34.52 (PCy2-CH), 36.1 7 (Ni- beta -OmicronEta2), 1 1 7.48, 123.26, 1 34.86, 1 62.1 1 (BAr4F), one aryl and one quaternary signal not located. 31 P{1 H} NMR (C6D5Br) : delta -8.70 (d, 2JP.P = 35.5 Hz, 1 P, PCy2), 1 9.24 (d, 2JP.P = 35.5 Hz, 1 P, PCy2). 19F NMR (C6D5Br): -62.95 (s).

Reference： [1]Patent: WO2014/130410,2014,A1 .Location in patent: Page/Page column 23; 24

51
[ 75-58-1 ]
[ 79060-88-1 ]
tetramethylammonium tetrakis-(3,5-bis(trifluoromethyl)phenyl)borate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 4295 - 4303
[2]Chemical Communications,2014,vol. 50,p. 10604 - 10607

52
[ 12112-67-3 ]
[ 1542796-07-5 ]
[ 79060-88-1 ]
{2-((2R,3R)-3-(tert-butyl)-4-methoxy-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)pyridine}(η⁴-1,5-cyclooctadiene)iridium (I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		A solution of 6a (100 mg, 0.332 mmol) and [IrCl(COD)]2 (115.0 mg, 0.166 mmol) in degassed CH2C12 (6 mL) is heated for 1 h at 45 C under argon. After cooling to room temperature, NaBArF (318 mg, 0.348 mmol) is added followed immediately by 10 ml of degassed water. The two layers are stirred vigorously for 30 min. After separation of the layers, the aqueous layer is extracted twice with CH2C12 (2 mL). The combined organic layer is dried over Na2S04 and concentrated to 1 mL. The mixture is then passed through a short plug of silica under argon using CH2C12 as eluent. The center of the first orange fraction is collected and dried to give 413 mg of 6a as a red-orange solid, 85% yield. 1H NMR (500 MHz, CD2C12) delta 8.09 (d, / = 6.0 Hz, 1H), 8.05 (t, / = 7.6 Hz, 1H), 7.98 (d, / = 7.8 Hz, 1H), 7.63 (s, BArF), 7.47 (s, BArF), 7.42 (t, J = 6.8 Hz, 1H), 7.32 (t, J = 8.3 Hz, 1H), 6.52-6.55 (m, 2H), 5.96 (s, 1H), 5.25-5.28 (m, IH), 5.05 (m, IH), 4.83-4.88 (m, IH), 4.41-4.43 (m, IH), 3.84 (s, 3H), 2.61-2.65 (m, IH), 2.30-2.42 (m, 2H), 2.22-2.28 (m, 2H), 2.01-2.07 (m, IH), 1.72-1.86 (m, 2H), 1.15 (d, JH-p = 16.2 Hz, 9H); 13C NMR (125 MHz, CD2C12) delta 164.7 (d, JC-p = 10.0 Hz), 162.7 (d, JC-p = 4.1 Hz), 161.5 (q, VC-B = 50.2 Hz), 160.4 (d, JC-p = 5.5 Hz), 147.8, 140.6 (d, JC-p = 0.9 Hz), 135.3 (d, JC-p = 1.4 Hz), 134.0 (br), 128.2 (qq, 2JC-v = 31.4 Hz, c-F = 2.8 Hz), 127.0, 126.4 (d, JC-p = 7.4 Hz), 125.7, 124.9 (q, VC-F = 272.3 Hz), 116.7 (sept, 3/C-F = 4.0 Hz), 105.2 (d, JC-p = 4.0 Hz), 104.4 (d, JC-p = 5.2 Hz), 94.6 (d, Jc-p = 9.7 Hz), 93.4 (d, JC-p = 13.7 Hz), 84.8 (d, JC-p = 24.2 Hz), 63.9 (d, JC-p = 19.8 Hz), 55.1, 34.7 (d, JC-p = 4.5 Hz), 34.5 (d, JC-p = 22.1 Hz), 29.9 (d, JC-p = 1.9 Hz), 29.8 (d, Jc-p = 1.9 Hz), 25.5 (d, JC-p = 2.4 Hz), 25.4 (d, JC-p = 4.5 Hz); 31P NMR (200 MHz, CD2C12) delta 47.33 (s); HRMS (ESI) mJz 602.1853 (M+), calc. for [IrC25H32N02P]+ 602.1795; 863.0658 (BArF), calc. for [C32H12BF24]" 863.0654.

Reference： [1]Patent: WO2015/6458,2015,A1 .Location in patent: Page/Page column 27; 28

53
[ 12112-67-3 ]
[ 1542796-16-6 ]
[ 79060-88-1 ]
{2-((2R,3R)-3-(tert-butyl)-4-methoxy-2,3-dihydrobenzo[d][1,3]oxaphosphol-2-yl)pyridine}(η⁴-1,5-cyclooctadiene)iridium (I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		General procedure: A solution of 6a (100 mg, 0.332 mmol) and [IrCl(COD)]2 (115.0 mg, 0.166 mmol) in degassed CH2C12 (6 mL) is heated for 1 h at 45 C under argon. After cooling to room temperature, NaBArF (318 mg, 0.348 mmol) is added followed immediately by 10 ml of degassed water. The two layers are stirred vigorously for 30 min. After separation of the layers, the aqueous layer is extracted twice with CH2C12 (2 mL). The combined organic layer is dried over Na2S04 and concentrated to 1 mL. The mixture is then passed through a short plug of silica under argon using CH2C12 as eluent. The center of the first orange fraction is collected and dried to give 413 mg of 6a as a red-orange solid, 85% yield. Complex 7g. After addition of NaBArF, the mixture is stirred at room temperature for 12 h until 31 P NMR indicates complete conversion. Compound 7g (431 mg) is isolated as a light yellow solid (87% yield) after the same work up as above. 1H NMR (500 MHz, CDC13) delta 7.69 (s, BArF), 7.64 (t, / = 8.1 Hz, IH), 7.49 (s, BArF), 7.45 (t, J = 8.5 Hz, IH), 7.32 (dd, 3/H-p = 7.1 Hz, / = 5.1 Hz, IH, OCH2), 7.23 (d, J = 7.1 Hz, IH), 6.89 (dd, / = 8.7, 1.0 Hz, IH), 6.72 (m, IH, OCH2), 6.69 (t, / = 4.0 Hz, IH), 6.66 (dd, / = 8.4, 1.8 Hz, IH), 6.50 (d, / = 6.3 Hz, IH), 4.37-4.39 (m, IH), 4.29-4.31 (m, 2H), 3.96 (s, 3H), 3.87-3.90 (m, IH), 2.57-2.62 (m, 2H), 2.18-2.32 (m, 2H), 1.95-2.01 (m, IH), 1.71-1.75 (m, IH), 1.51- 1.53 (m, IH), 1.21 (d, 7 =17.0 Hz, 9H), 0.83-0.93 (m, IH), - 13.34 (dd, 2/H-P = 22.8 Hz, / = 3.8 Hz, IH); 13C NMR (125 MHz, CDC13) delta 167.9 (d, JC-p = 9.3 Hz), 162.5 (d, / = 6.3 Hz), 162.3 (q, VC-B = 50.2 Hz), 160.3 (d, JC-p = 3.8 Hz), 153.1 (d, JC-p = 7.8 Hz), 141.6 (d, JC-p = 1.4 Hz), 136.5 (d, JC-p = 1.7 Hz), 134.8 (br), 129.0 (qq, 2JC-v = 31.5 Hz, c-F = 2.8 Hz), 125.6 (q, VC-F = 272.7 Hz), 117.7 (d, JC-p = 9.5 Hz), 117.4 (sept, 3/c-F = 4.1Hz), 111.1, 106.7 (d, JC-p = 3.8 Hz), 105.6 (d, JC-p = 5.4 Hz), 104.3 (d, JC-p = 38.2 Hz), 101.2 (t, JC-p = 2.3 Hz), 95.2 (t, JC-p = 1.9 Hz, COD, CH), 93.7 (d, JC-p = 29.0 Hz, COD, CH), 68.0 (d, JC-p = 1.9 Hz, COD, CH), 65.3 (d, JC-p = 3.6 Hz, COD, CH), 61.6 (dd, / = 57.0, 0.8 Hz, CH20), 55.7, 34.2 (dd, JC-p = 24.8, 0.8 Hz), 32.8 (d, JC-p = 4.5 Hz, COD, CH2), 31.7 (COD, CH2), 26.3 (d, / = 3.6 Hz, COD, CH2), 25.8 (COD, CH2), 25.4 (d, Jc-p = 3.6 Hz); 31P NMR (200 MHz, CDC13) delta 46.45 (d, / = 6.5 Hz); HRMS (ESI) m/z 632.1863 (M+), calc. for [IrC26H34N03P]+ 632.1900; 863.0648 (BArF), calc. for [C32Hi2BF24]" 863.0654.

Reference： [1]Patent: WO2015/6458,2015,A1 .Location in patent: Page/Page column 27; 28; 30; 31

54
[ 1375327-34-6 ]
[ 79060-88-1 ]
[methylpalladium(1-diisopropylphosphino-2-di(t-butyl)phosphinylbenzene)(2,6-lutidine)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane; at 20℃; for 0.333333h;Inert atmosphere;	Compound 7 was synthesized using Compound 4 as a raw material. That is, a methylene chloride suspension (8 ml) of ([methylpalladium(1-diisopropylphosphino-2-di(t-butyl)phosphinylbenzene)(2,6-lutidine)][hexafluoroantimonate) (Compound 4; 0.24 g; 0.30 mmol) and sodium [tetrakis(3,5-bis(trifluoromethyl)phenyl]borate (0.26 g, 0.30 mmol) was stirred at room temperature for 20 minutes under argon atmosphere. The reaction solution was filtered through a pad of Celite (dried diatom) and the filtrate was subjected to vacuum concentration. The yellow solid residue was washed with hexane, and dried under reduced pressure to obtain 0.14 g of Compound 7. The yield was 95%. 1H NMR (CDCl3) delta 7.97 (td, J = 7.6, 3.7 Hz, 1H), 7.71 (s, 8H), 7.68-7.59 (m, 4H), 7.51 (s, 4H), 7.17 (d, J = 7.5 Hz, 2H), 3.09 (s, 6H), 2.66-2.57 (m, 2H), 1.30-1.25 (m, 12H), 1.16 (d, J = 14.5 Hz, 18H), 0.37 (d, J = 2.0 Hz, 3H); 31P NMR (202 MHz, CDCl3) delta 58.20, 44.83.

Reference： [1]Patent: EP2848623,2015,A1 .Location in patent: Paragraph 0103; 0104

55
[ 108-48-5 ]
chloromethylpalladium[1-diisopropylphosphino-2-di(t-butyl)phosphinylbenzene] [ No CAS ]
[ 79060-88-1 ]
[methylpalladium(1-diisopropylphosphino-2-di(t-butyl)phosphinylbenzene)(2,6-lutidine)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane; at 20℃; for 0.333333h;Inert atmosphere;	Compound 7 was synthesized using Compound 8 represented by the following formula, which is an intermediate in the synthesis of Compound 4 in Synthesis Example 4, as a material. That is, a methylene chloride suspension (8 ml) of chloromethylpalladium[1-diisopropylphosphino-2-di(t-butyl)phosphinylbenzene] (Compound 8; 0.10 g; 0.20 mmol), sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (0.18 g, 0.20 mmol) and 2,6-dimethylpyridine (0.021 g, 0.20 mmol) was stirred at room temperature for 20 minutes under argon atmosphere. The reaction mixture was filtered through a pad of Celite (dried diatom) and the filtrate was subjected to vacuum concentration. The yellow solid residue was washed with hexane, and dried under reduced pressure to obtain 0.26 g of Compound 7. The yield was 90%. The 1H- and 31P-NMR spectra of Compound 7 were coincident with those described in Synthesis Example 7.

Reference： [1]Patent: EP2848623,2015,A1 .Location in patent: Paragraph 0105

56
[ 108-48-5 ]
(chloromethylpalladium[1-bis(2-methylphenyl)phosphino-2-di(tbutyl)phosphinylbenzene]) [ No CAS ]
[ 79060-88-1 ]
[methylpalladium(1-bis(2-methylphenyl)phosphino-2-di(t-butyl)phosphinylbenzene)(2,6-lutidine)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane; at 20℃; for 1.5h;Inert atmosphere;	Compound 12 was synthesized in a similar manner to that described in Synthesis Example 7. That is, a methylenechloride suspension (3 ml) of Compound 11 (0.082 g, 0.14 mmol), 2,6-dimethylpyridine (0.029 g, 0.27 mmol) and sodiumtetrakis[(3,5-bis(trifluoromethyl)phenyl]borate (0.12 g, 0.14 mmol) was stirred at room temperature for 1.5 hour underargon atmosphere. The reaction mixture was filtered through a pad of Celite (dried diatom) and the filtrate was subjectedto vacuum concentration. The residue was subjected to reprecipitation from methylene chloride and pentane to obtain0.19 g of Compound 12. The yield was 90%.[0115] 1H NMR (CD2Cl2) delta 7.79-7.46 (m, 21H), 7.32-7.30 (m, 2H), 7.22 (2H, t, J = 7.2 Hz), 7.14-7.12 (m, 1H), 6.63(dd, J = 11.3, 8.1 Hz, 1H), 3.12 (s, 3H), 3.09 (s, 3H), 2.94 (s, 3H), 2.28 (s, 3H), 1.04 (d, J = 14.4 Hz, 9H), 0.97 (d, J =14.7 Hz, 9H), 0.18 (d, J = 2.7 Hz, 3H) ; 31P NMR (202 MHz, CD2Cl2) delta 64.25 (s, P(O)t-Bu2), 27.37 (s, PAr?2); Anal. Calc?dfor C68H60BF24NOP2Pd: C, 52.95; H, 3.92; N, 0.91. Found: C, 52.57; H, 3.94; N, 0.57.

Reference： [1]Patent: EP2848623,2015,A1 .Location in patent: Paragraph 0114; 0115

57
(Pd(o-C6H4NHCMe=O))2(μ-Cl)2 [ No CAS ]
[ 1375327-53-9 ]
[ 79060-88-1 ]
[ 1375327-40-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	In dichloromethane; at -78 - 25℃; for 3.5h;	o-(i-Pr2P)C6H4(P(O)t-Bu2) (142 mg, 0.401 mmol) as free BPMO and Compound A (110 mg, 0.199 mmol) weredissolved in 7 ml of methylene chloride and stirred at 25C for three hours. The solution was poured slowly into silverhexafluoroantimonate (0.31 g, 0.90 mmol) in a flask cooled to -78C. After vigorous stirring at 25C for 30 minutes, theresultant solution was condensed by removing silver chloride through Celite filtration. Toluene was poured into thesolution to obtain precipitate. The precipitate was recrystallized from methylene chloride to thereby obtain Compound5 as a pale orange crystals which were stable in air and humid condition. The yield was 73%.[0100] 1H NMR (CD2Cl2, 500 MHz) delta 8.96 (s, 1H), 8.00-7.97 (m, 1H), 7.81-7.72 (m, 3H), 7.24 (ddd, J = 7.7, 4.7, 1.1Hz, 1H), 7.09 (t, J = 7.1 Hz, 1H), 6.98-6.92 (m, 2H), 2.41 (s, 3H), 1.42 (d, J = 14.4 Hz, 18H), 1.22 (dd, J = 15.4, 7.1 Hz,6H), 1.03 (dd, J = 18.3, 7.1 Hz, 6H) ; 13C-NMR (CD2Cl2, 102 MHz) delta 172.55 (d, J = 3 Hz), 138.26 (d, J = 7 Hz), 135.80(d, J = 9 Hz), 135.12, 134.36 (d, J = 11 Hz), 133.35 (dd, J = 13, 8 Hz), 132.17 (dd, J = 6, 3 Hz), 131.46 (dd, J = 33, 4Hz), 130.73 (dd, J = 12, 2 Hz), 126.49, 125.51 (d, J = 4 Hz), 125.19 (d, J = 2 Hz), 118.50, 38.04 (d, J = 57 Hz), 27.83,27.76 (d, J = 24 Hz), 22.49 (d, J = 4 Hz), 19.99 (d, J = 4 Hz), 19.28; 31P NMR (CD2Cl2, 202 MHz) delta 63.07, 52.30; Anal.Calc?d for C28H44F6NOP2PdSb: C, 40.48; H, 5.34; N, 1.69. Found: C, 40.20; H, 5.41; N, 1.53.

Reference： [1]Patent: EP2848623,2015,A1 .Location in patent: Paragraph 0098 - 0100; 0101; 0102

58
[Rh(Cp*)(2-(2-pyridyl)-μ-phenoxide)]₂[B(Ar^F)₄]₂ [ No CAS ]
[ 27126-93-8 ]
[ 79060-88-1 ]
[Rh(Cp*)(phpy)(NCAr^F)][B(Ar^F)₄] [ No CAS ]

Reference： [1]Organometallics,2014,vol. 33,p. 4442 - 4448

59
C₄₇H₃₅ClN₂Pd [ No CAS ]
[ 27126-93-8 ]
[ 79060-88-1 ]
C₅₆H₃₈F₆N₃Pd⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 456 - 464

60
C₃₉H₃₅ClN₂Pd [ No CAS ]
[ 27126-93-8 ]
[ 79060-88-1 ]
C₄₈H₃₈F₆N₃Pd⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 456 - 464

61
Cl^(1-)*C₄₆H₄₁F₃IrN₈O₅⁽¹⁺⁾ [ No CAS ]
[ 79060-88-1 ]
C₄₆H₄₁F₃IrN₈O₅⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In dichloromethane; at 20℃; for 0.166667h;	General procedure: A suspension of the iridium dimer S3a or S3b (0.15 mmol), 2,2,2-trifluoro-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-acetamide (84.6 mg, 0.33 mmol) in ethanol (15.0 mL) was heated at 95 C for 16-24 h under argon. The reaction mixture was concentrated to dryness and subjected to a flash silica gel chromatography (CH2Cl2/MeOH = 100:1) to give the pure yellow solid as a chloride salt. The product was directly suspended in CH2Cl2. An equal amount of <strong>[79060-88-1]sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate</strong> (NaBArF24) was added in one portion and the mixture was stirred for 10 minutes at room temperature. The white salt was filtered off. After removal of the solvent in vacuo, the residue was taken up in minimum amount of CHCl3 (about 4.0mL) and washed with excess water and centrifuged. The organic layer was dried and concentrated in vacuo to give the product Rac-Ir3 or Rac-Ir4 as the borate salt.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4653 - 4656

62
Cl^(1-)*C₄₆H₄₁F₃IrN₈O₃S₂⁽¹⁺⁾ [ No CAS ]
[ 79060-88-1 ]
C₄₆H₄₁F₃IrN₈O₃S₂⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In dichloromethane; at 20℃; for 0.166667h;	General procedure: A suspension of the iridium dimer S3a or S3b (0.15 mmol), 2,2,2-trifluoro-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)-acetamide (84.6 mg, 0.33 mmol) in ethanol (15.0 mL) was heated at 95 C for 16-24 h under argon. The reaction mixture was concentrated to dryness and subjected to a flash silica gel chromatography (CH2Cl2/MeOH = 100:1) to give the pure yellow solid as a chloride salt. The product was directly suspended in CH2Cl2. An equal amount of <strong>[79060-88-1]sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate</strong> (NaBArF24) was added in one portion and the mixture was stirred for 10 minutes at room temperature. The white salt was filtered off. After removal of the solvent in vacuo, the residue was taken up in minimum amount of CHCl3 (about 4.0mL) and washed with excess water and centrifuged. The organic layer was dried and concentrated in vacuo to give the product Rac-Ir3 or Rac-Ir4 as the borate salt.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4653 - 4656

63
C₄₆H₄₁F₃IrN₈O₅⁽¹⁺⁾*C₂F₃O₂^(1-) [ No CAS ]
[ 79060-88-1 ]
C₄₆H₄₁F₃IrN₈O₅⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In dichloromethane; at 20℃; for 0.166667h;	A suspension of the iridium auxiliary complex Lambda-S4a (98.2 mg, 0.11 mmol), 2,2,2-trifluoro-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)acetamide (51.2 mg, 0.12 mmol), and trifluoroaceticacid (11.4 mg, 0.10 mmol) in acetonitrile (18.0 mL) was heated at 65 C for 2 h under argon in the dark. The reaction mixture was concentrated and subjected to a flash silica gel chromatography (MeOH/CH2Cl2 = 1:100) to give the pure yellow solid as a trifluoroacetic salt (115.0 mg, 0.10mmol, 94%). The product was directly suspended in CH2Cl2. Sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (NaBArF24) (88.6 mg, 0.10 mmol) was added in one portion and the mixture was stirred for 10 minutes at room temperature. The white salt was filtered off. After removal of the solvent in vacuo, the residue was taken up in minimum amount of CHCl3 (about 2.0 mL) and washed with excess water and centrifuged. The organic layer was dried and concentrated in vacuo to give the pure yellow solid as the borate salt (173.7 mg, 0.099 mmol, 90%). The absolute configuration was identified as Lambda by CD spectra (see below).

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4653 - 4656

64
C₄₆H₄₁F₃IrN₈O₅⁽¹⁺⁾*C₂F₃O₂^(1-) [ No CAS ]
[ 79060-88-1 ]
C₄₆H₄₁F₃IrN₈O₃S₂⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In dichloromethane; at 20℃; for 0.166667h;	A suspension of the iridium auxiliary complex Lambda-S4b (46.3 mg, 0.050 mmol), 2,2,2-trifluoro-N-(3-(pyridin-2-yl)-1H-pyrazol-5-yl)acetamide (14.1 mg, 0.055 mmol), and trifluoroacetic acid (3.2 mg, 0.028 mmol) in acetonitrile (5.0 mL) was heated at 65 C for 2 h under argon in the dark. The reaction mixture was concentrated to dryness and subjected to a flash silicagel chromatography (MeOH/CH2Cl2 = 1:80) to give the pure yellow solid as a trifluoroacetic salt (62.5 mg, 0.048 mmol, 95%). The product was directly suspended in CH2Cl2. Sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (NaBArF24) (42.5 mg, 0.048 mmol) was added in one portion and the mixture was stirred for 10 minutes at room temperature. The white salt was filtered off. After removal of the solvent in vacuo, the residue was taken up in minimum amount of CHCl3 (about 2.0 mL) and washed with excess water and centrifuged. The organic layer was dried and concentrated in vacuo to give the pure yellow solid as the borate salt (92.2 mg, 0.047 mmol, 94%).The absolute configuration was identified as Lambda by CD spectra (see below).

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4653 - 4656

65
methallylnickel chloride dimer [ No CAS ]
methyl 1-(1-((2,6-diisopropylphenyl) imino)ethyl)-1H-indazole-3-carboxylate [ No CAS ]
[ 79060-88-1 ]
C₂₇H₃₄N₃NiO₂⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In dichloromethane; at 20℃; for 2h;Inert atmosphere; Schlenk technique; Glovebox;	Methyl-1-(1-((2,6-diisopropylphenyl) imino) ethyl)-1H-indazole-3-carboxylate (1) (40 mg, 0.105 mmol) and NaBAr'4 (Sodium-tetrakis(3,5-bis(trifluoromethyl) phenyl) borate) (94 mg; 0.105 mmol) were mixed in dichloromethane (20 ml). The suspension was stirred vigorously and a solution of [(eta3-CH3C(CH2)2)NiCl]2 [12] (16 mg, 0.053 mmol) in dichloromethane was added. The mixture was stirred for 2 h at room temperature. The resulting solution was filtered through celite and the product was crystallized adding pentane and storing at -20 C. 4 was obtained as dark orange crystalline solid in 70% yield (100 mg; 0.074 mmol). 1H NMR (400 MHz, CD3Cl, 298 K): delta/ppm = 8.10 (d, J = 8.3 Hz, 1H), 7.69 (m, 1H), 7.67 (s, 8H), 7.49 (m, 2H), 7.46 (s, 4H), 7.38 (t, J = 7.7 Hz, 1H), 7.29 (m, 2H), 4.12 (s, 3H), 3.82 (s, 1H), 3.23 (hept, J = 6.8 Hz, 1H), 2.84 (hept, J = 6.8 Hz, 1H), 2.79 (s, 1H), 2.59 (s, 3H), 2.52 (s, 1H), 2.37 (s, 1H), 2.21 (s, 3H), 1.31 (d, J = 6.8 Hz, 6H), 1.17 (d, J = 6.8 Hz, 3H), 1.07 (d, J = 6.8 Hz, 3H). 13C{1H} NMR (100 MHz, CDCl3, 298 K,): delta/ppm = 161.4 (t, JCF = 49 Hz), 160.7, 159.6, 139.4, 138.8, 134.8, 133.1, 129.0, 127.5, 125.1, 124.8, 124.5, 124.5 (q, JCF = 270 Hz), 117.4, 111.7, 63.2, 61.4, 54.1, 28.9, 28.8, 24.2, 24.0, 23.6, 23.2, 22.5, 17.3. 19F NMR (400 MHz, CDCl3, 298 K): delta/ppm = -62.45. 11B{1H} NMR (400 MHz, CDCl3, 298 K): delta/ppm = -6.65 (nu1/2 ?11 Hz). Elemental analysis (%) C59H46BF24N3NiO2 (M = 1354.48 g/mol): calculated C 52.32, H 3.42, N 3.10; found C 52.12, H 3.50, N 3.05. For additional 2D NMR spectrum and assignments data see Supplementary data.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2016,vol. 414,p. 19 - 26

66
methallylnickel chloride dimer [ No CAS ]
methyl (E)-1-(1-((2,6-diisopropylphenyl)imino)ethyl)-1H-indazole-5-carboxylate [ No CAS ]
[ 79060-88-1 ]
C₂₇H₃₄N₃NiO₂⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In dichloromethane; at 20℃; for 2h;Inert atmosphere; Schlenk technique; Glovebox;	Methyl-1-(1-((2,6-diisopropylphenyl) imino) ethyl)-1H-indazole-5-carboxylate (2) (40 mg, 0105 mmol) and NaBAr'4 (Sodium-tetrakis(3,5-bis(trifluoromethyl) phenyl) borate) (94 mg; 0.105 mmol) were mixed in dichloromethane (20 ml). The suspension was stirred vigorously and a solution of [(eta3-CH3C(CH2)2)NiCl]2 [12] (16 mg, 0.053 mmol) in dichloromethane was added. The mixture was stirred for 2 h at room temperature. The resulting pale orange solution was filtered through celite and the product was crystallized adding pentane and storing at -20 C. 5 was obtained as orange solid in 80% yield (115 mg; 0.085 mmol). 1H NMR (400 MHz, CD3Cl, 298 K): delta/ppm = 8.60 (s, 1H), 8.46 (s, 1H), 8.41 (d, J = 9 Hz, 1H), 7.77 (d, J = 9 Hz, 1H), 7.69 (s, 8H), 7.48 (s, 4H), 7.39 (t, J = 7.8 Hz, 1H), 7.31 (d, J = 9 Hz, 2H), 3.99 (s, 3H), 3.50 (s, 1H), 3.20 (hept, J = 6.8 Hz, 1H), 2.85 (hept, J = 6.8 Hz, 1H'), 2.65 (s, 1H), 2.60 (s, 3H), 2.57 (s, 1H), 2.38 (s, 1H), 2.17 (s, 3H), 1.30 (d, J = 6.8 Hz, 6H), 1.17 (d, J = 6.8 Hz, 3H), 1.08 (d, J = 6.8 Hz, 3H). 13C{1H} NMR (100 MHz, CDCl3, 298 K,): delta/ppm = 164.6, 161.6 (t, JCF = 50 Hz), 160.3, 146.3, 140.0, 139.9, 139.7, 134.8, 134.4, 133.6, 129.0, 128.7, 126.1, 125.0, 124.5 (q, JCF = 270 Hz), 117.4, 111.4, 62.9, 56.8, 52.9, 28.9, 28.7, 24.1, 23.9, 23.5, 23.1, 23.0, 16.4. 19F NMR (400 MHz, CDCl3, 298 K): delta/ppm = -62.40. 11B{1H} NMR (400 MHz, CDCl3, 298 K): delta/ppm = -6.53 (nu1/2 ?11 Hz). Elemental analysis (%) C59H46BF24N3NiO2 (M = 1354.48 g/mol): calculated C 52.32, H 3.42, N 3.10; found C 52.39, H 3.53, N 3.15. For additional 2D NMR spectrum and assignments data see Supplementary data.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2016,vol. 414,p. 19 - 26

67
methallylnickel chloride dimer [ No CAS ]
methyl (E)-1-(1-((2,6-diisopropylphenyl)imino)ethyl)-1H-indazole-6-carboxylate [ No CAS ]
[ 79060-88-1 ]
C₂₇H₃₄N₃NiO₂⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In dichloromethane; at 20℃; for 2h;Inert atmosphere; Schlenk technique; Glovebox;	Methyl-1-(1-((2,6-diisopropylphenyl) imino) ethyl)-1H-indazole-6-carboxylate (3) (40 mg, 0105 mmol) and NaBAr'4 (Sodium-tetrakis(3,5-bis(trifluoromethyl) phenyl) borate) (94 mg; 0.105 mmol) were mixed in dichloromethane (20 ml). The suspension was stirred vigorously and a solution of [(eta3-CH3C(CH2)2)NiCl]2 [12] (16 mg, 0.053 mmol) in dichloromethane was added. The mixture was stirred for 2 h at room temperature. The resulting orange solution was filtered through celite and the product was crystallized adding pentane and storing at -20 C. 6 was obtained as brown orange solid in 75% yield (108 mg; 0.079 mmol). 1H NMR (400 MHz, CD3Cl, 298 K): delta/ppm = 8.35 (s, 1H), 8.26 (s, 1H), 7.96 (d, J = 8.4 Hz, 1H), 7.64 (d, J = 8.7 Hz, 1H), 7.60 (s, 8H), 7.38 (s, 4H), 7.29 (t, J = 7.8 Hz, 1H), 7.20 (m, 2H), 3.83 (s, 3H), 3.40 (s, 1H), 3.11 (hept, J = 6.8 Hz, 1H), 2.76 (hept, J = 6.8 Hz, 1H), 2.57 (s, 1H), 2.57 (s, 3H), 2.49 (s, 1H), 2.30 (s, 1H), 2.07 (s, 3H), 1.20 (d, J = 6.8 Hz, 6H), 1.08 (d, J = 6.8 Hz, 3H), 0.99 (d, J = 6.8 Hz, 3H). 13C{1H} NMR (100 MHz, CDCl3, 298 K,): delta/ppm = 165.7, 161.8 (t, JCF = 50 Hz), 160.5, 145.4, 140.2, 139.9, 139.5, 138.0, 134.9, 134.0, 129.2, 129.2, 127.0, 125.2, 124.7 (q, JCF = 270 Hz), 124.0, 117.6, 113.2, 63.2, 57.1, 53.4, 29.1, 28.9, 24.2, 24.0, 23.6, 23.2, 23.1, 16.6, C23 (n.o.). 19F NMR (400 MHz, CDCl3, 298 K): delta/ppm = -62.37. 11B{1H} NMR (400 MHz, CDCl3, 298 K): delta/ppm = -6.64 (nu1/2 ?11 Hz). Elemental analysis (%) C59H46BF24N3NiO2 (M = 1354.48 g/mol): calculated C 52.32, H 3.42, N 3.10; found C 52.25, H 3.36, N 3.01. For additional 2D NMR spectrum and assignments data see Supplementary data.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2016,vol. 414,p. 19 - 26

68
[ 12112-67-3 ]
2-((4S,5S)-2-(1-(diphenylphosphino)-2-methylpropan-2-yl)-5-methyl-4,5-dihydrooxazol-4-yl)propan-2-ol [ No CAS ]
[ 79060-88-1 ]
C₃₁H₄₂IrNO₂P⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		Ligand 14 (30.0 mg, 78.0 mol, 1.00 equiv) and bis(1,5-cyclooctadiene)diiridium(I) dichloride (26.0 mg, 39.0 mol, 0.50 equiv) were dissolved in 3 mL dry CH2Cl2 and refluxed for 2.5 h under argon. Then of NaBArF (90.0 mg, 101 mmol, 1.30 equiv) were added and the mixture stirred for 30 min at rt. Silica gel (2 g) was added and the solvent removed on a rotavap. The immobilized complex was transferred to a silica gel column (2 × 12 cm). The column was flushed with 100 mL of Et2O followed by 100 mL of CH2Cl2. The orange product, eluted by CH2Cl2, was collected in one fraction. The resulting orange solution was concentrated under vacuum and the resulting solid dissolved in CHCl3 and concentrated again to remove residual water. The addition/evaporation of CHCl3 was repeated three times. After drying the residue under high vacuum, 119 mg (78.0 mol, 99% yield) of complex Ir-14-OHwas obtained as an orange solid.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 1185 - 1195

69
[ 12112-67-3 ]
(4S,5S)-2-(1-(diphenylphosphino)-2-methylpropan-2-yl)-5-methyl-4-(2-((triethylsilyl)oxy)propan-2-yl)-4,5-dihydrooxazole [ No CAS ]
[ 79060-88-1 ]
C₃₂H₁₂BF₂₄^(1-)*C₃₇H₅₆IrNO₂PSi⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		General procedure: Ligand 14 (30.0 mg, 78.0 mol, 1.00 equiv) and bis(1,5-cyclooctadiene)diiridium(I) dichloride (26.0 mg, 39.0 mol, 0.50 equiv) were dissolved in 3 mL dry CH2Cl2 and refluxed for 2.5 h under argon. Then of NaBArF (90.0 mg, 101 mmol, 1.30 equiv) were added and the mixture stirred for 30 min at rt. Silica gel (2 g) was added and the solvent removed on a rotavap. The immobilized complex was transferred to a silica gel column (2 × 12 cm). The column was flushed with 100 mL of Et2O followed by 100 mL of CH2Cl2. The orange product, eluted by CH2Cl2, was collected in one fraction. The resulting orange solution was concentrated under vacuum and the resulting solid dissolved in CHCl3 and concentrated again to remove residual water. The addition/evaporation of CHCl3 was repeated three times. After drying the residue under high vacuum, 119 mg (78.0 mol, 99% yield) of complex Ir-14-OHwas obtained as an orange solid.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 1185 - 1195

70
[ 12112-67-3 ]
(S)-2-(1-(diphenylphosphino)-2-methylpropan-2-yl)-4-isopropyl-5,5-diphenyl-4,5-dihydrooxazole [ No CAS ]
[ 79060-88-1 ]
C₄₂H₄₈IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		The ligand (120 mg, 237 mumol, 1.00 equiv) and the iridium precursor (87.7 mg, 131 mumol,0.50 equiv) were placed in a J.-Young-tube, the atmosphere was exchanged to argon and2 mL of dry CH2Cl2 were added. The solution was heated to 50 C for 45 min and then cooledto rt. NaBArF (252 mg, 284 mumol, 1.20 equiv) were added and the solution was stirred for30 min. Silica gel was added and the solvent was removed on a rotovap. The complex waspurified by filtration over silica (40 g, h×d, 12 cm×3 cm) using 200 mL of MTBE followed by200 mL of CH2Cl2. The complex was obtained as an orange solid (359 mg, 215 mumol, 91%).

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 1185 - 1195

71
methallylnickel chloride dimer [ No CAS ]
[ 1014-60-4 ]
[ 79060-88-1 ]
C₁₈H₂₉Ni⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 6723 - 6726

72
methallylnickel chloride dimer [ No CAS ]
[ 1460-02-2 ]
[ 79060-88-1 ]
C₂₂H₃₇Ni⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 6723 - 6726

73
3-hexyl-1-(4-methoxyphenyl)-1H-imidazol-3-ium iodide [ No CAS ]
[ 79060-88-1 ]
C₁₆H₂₃N₂O⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In dichloromethane; at 20℃; for 24h;	1.51 g (3.9 mmol) imidazolium iodide salt (2c) were dissolved in dichloromethane (14 mL) and 3.46 gNaB[3,5-(CF3)2C6H3]4 (3.9 mmol, 1 eq) was added. After stirring the reaction mixture at roomtemperature for 24 hours the precipitate was filtered off and the remaining solvent was removed. Theproduct was dried in vacuo and obtained as orange solid (4.19 g, 3.7 mmol, 96 %).m.p. 69 C.1H-NMR (300 MHz, CDCl3): delta = 8.19 (s, 1H, NCHN), 7.69 (s, 8H, B-Ar-H), 7.51 (s, 4H, B-Ar-H),7.27 (m, 1H, NCHCHN), 7.13 (d, J = 8.9 Hz, 3H, Ar-H + NCHCHN), 6.99 (d, J = 9.0 Hz, 2H, Ar-H),4.05 (t, J = 7.6 Hz, 2H, NCH2), 3.82 (s, 3H, p-OCH3), 1.85 (m, 2H, NCH2CH2), 1.28 (m, 6H,CH2CH3), 0.85 (t, J = 6.9 Hz, 3H, CH2CH3) ppm.13C-NMR (75.5 MHz, CDCl3): delta = 162.0 (Ci-p-OCH3), 161.6 (q, JB = 50 Hz, 4 Ci-B), 134.7 (s, 8 B-Ar-C), 131.8 (NCHN), 129.1 (qq, JF = 31 Hz, JB = 2.7 Hz, 8 Ci-CF3), 126.0 (Ci-N), 124.5 (q, JF = 272 Hz,CF3), 123.6 (2 Ar-C), 123.0 (NCHCHN), 122.7 (NCHCHN), 117.5 (m, 4 B-Ar-C), 116.0 (2 Ar-C), 55.7 (p-OCH3), 51.0 (NCH2) 30.9 (NCH2CH2), 30.7, 29.8 (alkyl-CH2), 22.1 (CH2CH3), 13.6 (CH2CH3)ppm.19F-NMR (283 MHz, CDCl3): delta = -63.0 (CF3) ppm.Elemental analysis for C48H35N2OBF24: calcd. C = 51.36, H = 3.14, N = 2.50, found C = 51.47, H= 3.17, N = 2.48.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 3453 - 3456

74
1-(4-methoxyphenyl)-3-undecyl-1H-imidazol-3-ium bromide [ No CAS ]
[ 79060-88-1 ]
C₂₁H₃₃N₂O⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane; at 20℃; for 24h;	0.50 g (1.2 mmol) imidazolium bromide salt (2d) were dissolved in dichloromethane (14 mL) and1.08 g NaB[3,5-(CF3)2C6H3]4 (1.2 mmol, 1 eq) was added. After stirring the reaction mixture at roomtemperature for 24 hours the precipitate was filtered off and the remaining solvent was removed. Theproduct was dried in vacuo and obtained as orange liquid (1.38 g, 1.2 mmol, 95 %).DSC: Tgc: -23 C, Trecryst: -68 C, Tmelt: -20 C1H-NMR (300 MHz, CDCl3): delta = 8.21 (s, 1H, NCHN), 7.72 (s, 8H, B-Ar-H), 7.53 (s, 4H, B-Ar-H),7.29 (s, 1H, NCHCHN), 7.16 (d, J = 8.9 Hz, 3H, Ar-H + NCHCHN), 6.98 (d, J = 9.1 Hz, 2H, Ar-H),4.08 (t, J = 7.5 Hz, 2H, NCH2), 3.80 (s, 3H, p-OCH3), 1.87 (m, 2H, NCH2CH2), 1.26 (m, 16H,CH2CH3), 0.87 (t, J = 6.9 Hz, 3H, CH2CH3) ppm.13C-NMR (75.5 MHz, CDCl3): delta = 162.0 (Ci-p-OCH3), 161.6 (q, JB = 50 Hz, 4 Ci-B), 134.8 (s, 8 B-Ar-C), 131.8 (NCHN), 129.0 (qq, JF = 31 Hz, JB = 2.7 Hz, 8 Ci-CF3), 126.0 (Ci-N), 124.5 (q, JF = 272 Hz,CF3), 123.6 (2 Ar-C), 123.0 (NCHCHN), 122.7 (NCHCHN), 117.5 (m, 4 B-Ar-C), 115.9 (2 Ar-C),55.7 (p-OCH3), 51.0 (NCH2) 31.8 (NCH2CH2), 29.8, 29.4, 29.3, 29.2, 29.1, 28.6, 26.1 (alkyl-CH2),22.6 (CH2CH3), 14.0 (CH2CH3) ppm.19F-NMR (283 MHz, CDCl3): delta = -63.0 (CF3) ppm.Elemental analysis for C53H45N2OBF24: calcd. C = 53.37, H = 3.80 N = 2.35, found C = 53.15, H= 3.62, N = 2.54.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 3453 - 3456

75
[ 286014-44-6 ]
[ 79060-88-1 ]
C₁₃H₁₇N₂⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	In dichloromethane; at 20℃; for 24h;	0.51 g (1.5 mmol) imidazolium iodide salt (3a) were dissolved in dichloromethane (14 mL) and 1.37 gNaB[3,5-(CF3)2C6H3]4 (1.5 mmol, 1 eq) was added. After stirring the reaction mixture at roomtemperature for 24 hours the precipitate was filtered off and the remaining solvent was removed. Theproduct was dried in vacuo and obtained as pale yellow solid (1.57 g, 1.5 mmol, 96 %). m.p. 102 C.1H-NMR (300 MHz, CDCl3): delta = 7.97 (s, 1H, NCHN), 7.68 (s, 8H, B-Ar-H), 7.52 (s, 4H, B-Ar-H),7.19 (s, 1H, NCHCHN), 7.16 (t, J = 1.7 Hz, 1H, NCHCHN), 7.02 (s, 2H, Ar-H), 3.83 (s, 3H, NCH3),2.34 (s, 3H, p-CH3), 1.90 (s, 6H, o-CH3) ppm.13C-NMR (75.5 MHz, CDCl3): delta = 161.6 (q, JB = 50 Hz, 4 Ci-B), 142.8 (Ci-p-CH3), 134.7 (s, 8 B-Ar-C+NCHN), 133.6 (2 Ci-o-CH3), 130.3 (2 Ar-C), 129.5 (Ci-N), 128.9 (qq, JF = 32 Hz, JB = 2.7 Hz, 8 Ci-CF3), 124.9 (NCHCHN), 124.5 (q, JF = 273 Hz, CF3), 124.0 (NCHCHN), 117.5 (m, 4 B-Ar-C), 36.7(NCH3), 21.0 (p-CH3), 16.8 (2 o-CH3) ppm.19F-NMR (283 MHz, CDCl3): delta = -63.0 (CF3) ppm.Elemental analysis for C45H29N2BF24: calcd. C = 50.77, H = 2.75, N = 2.63, found C = 50.45, H =2.64, N = 2.60.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 3453 - 3456

76
[ 1174062-45-3 ]
[ 79060-88-1 ]
C₁₆H₂₃N₂⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In dichloromethane; at 20℃; for 24h;	0.57 g (1.5 mmol) imidazolium iodide salt (3b) were dissolved in dichloromethane (14 mL) and 1.35 gNaB[3,5-(CF3)2C6H3]4 (1.5 mmol, 1 eq) was added. After stirring the reaction mixture at roomtemperature for 24 hours the precipitate was filtered off and the remaining solvent was removed. Theproduct was dried in vacuo and obtained as pale yellow solid (1.59 g, 1.4 mmol, 94 %).m.p. 86 C.1H-NMR (300 MHz, CDCl3): delta = 8.01 (s, 1H, NCHN), 7.69 (s, 8H, B-Ar-H), 7.52 (s, 4H, B-Ar-H),7.29 (t, J = 1.7 Hz, 1H, NCHCHN), 7.18 (t, J = 1.7 Hz, 1H, NCHCHN), 7.01 (s, 2H, Ar-H), 4.12 (t, J =7.4 Hz, 2H, NCH2), 2.33 (s, 3H, p-CH3), 1.90 (s, 6H, o-CH3), 1.84 (m, 2H, NCH2CH2), 1.29 (m, 2H,CH2CH3), 0.91 (t, J = 7.2 Hz, 3H, CH2CH3) ppm.13C-NMR (75.5 MHz, CDCl3): delta = 161.6 (q, JB = 50 Hz, 4 Ci-B), 142.8 (Ci-p-CH3), 134.8 (s, 8 B-Ar-C), 133.9 (NCHN), 133.5 (2 Ci-o-CH3), 130.2 (2 Ar-C), 129.5 (Ci-N), 128.8 (qq, JF = 31 Hz, JB = 2.8Hz, 8 Ci-CF3), 124.8 (NCHCHN), 124.5 (q, JF = 272 Hz, CF3), 122.8 (NCHCHN), 117.5 (m, 4 B-Ar-C), 50.8 (NCH2), 31.6 (NCH2CH2), 20.9 (p-CH3), 19.2 (CH2CH3), 16.8 (2 o-CH3), 12.8 (CH2CH3)ppm.19F-NMR (283 MHz, CDCl3): delta = -63.0 (CF3) ppm.Elemental analysis for C48H35N2BF24: calcd. C = 52.10, H = 3.19, N = 2.53, found C = 51.76, H =3.07, N = 2.53.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 3453 - 3456

77
trans-[Mo(N₂C₆H₁₁)I(dppe)2] [ No CAS ]
[ 27126-93-8 ]
[ 79060-88-1 ]
[(1,2-bis(diphenylphosphino)ethane)₂(3,5-(CF₃)₂C₆H₃CN)Mo(NNCy)][((3,5-(CF₃)₂C₆H₃)₄)B] [ No CAS ]

Reference： [1]Dalton Transactions,2016,vol. 45,p. 15922 - 15930

78
[ 79060-88-1 ]
[ 171058-17-6 ]
[HMIM][tetrakis{3,5-bis(trifluoromethyl)phenyl}borate] [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 1677 - 1686

79
[ 92507-97-6 ]
[ 79060-88-1 ]
[EDMIM][tetrakis{3,5-bis(trifluoromethyl)phenyl}borate] [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 1677 - 1686

80
[ 15471-17-7 ]
[Mo{N-2,6-(Me₂)C₆H₃}(CHCMe₂Ph)(1,3-dimesitylimidazolin-2-ylidene)(OTf)(OC₆F₅)] [ No CAS ]
[ 79060-88-1 ]
[Mo(N-2,6-(Me₂)C₆H₃)(CHCMe₂Ph)(1,3-dimesitylimidazolin-2-ylidene)(OC₆F₅)(pyridiniumpropanesulfonate)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate] [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 6398 - 6405

81
[ 79060-88-1 ]
[ 3558-69-8 ]
C₁₇H₁₃N*C₃₂H₁₂BF₂₄^(1-)*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 13126 - 13140

82
[ 60-31-1 ]
[ 79060-88-1 ]
2-acetyloxy-N,N,N-trimethylethanaminium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 2808 - 2816

83
[ 1202-34-2 ]
[ 578743-87-0 ]
[ 79060-88-1 ]
[Cu(1,3-bis(-2,6-di-isopropylphenyl)imidazol-2-ylidene)(2,2'-dipyridylamine)][B(3,5-(CF₃)₂Ph)₄] [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2019,vol. 893,p. 21 - 31

84
[ 12126-50-0 ]
[ 79060-88-1 ]
[ 220517-48-6 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 10625 - 10632

85
[ 6331-09-5 ]
[ 79060-88-1 ]
C₅H₁₁NO₂*C₃₂H₁₂BF₂₄^(1-)*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 56,p. 161 - 164

86
[ 26348-61-8 ]
[ 79060-88-1 ]
C₅H₁₁NO₃*C₃₂H₁₂BF₂₄^(1-)*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 56,p. 161 - 164

87
[ 2899-36-7 ]
[ 79060-88-1 ]
C₇H₁₅NO₂S*C₃₂H₁₂BF₂₄^(1-)*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 56,p. 161 - 164

88
[ 930-73-4 ]
[ 79060-88-1 ]
[ 1616961-44-4 ]

Reference： [1]Journal of Physical Organic Chemistry,2020

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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 79060-88-1 ] {[proInfo.proName]}

Quality Control of [ 79060-88-1 ]

Related Doc. of [ 79060-88-1 ]

Product Details of [ 79060-88-1 ]

Calculated chemistry of [ 79060-88-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 79060-88-1 ]

Application In Synthesis of [ 79060-88-1 ]

[ 79060-88-1 ] Synthesis Path-Upstream 1~5

[ 79060-88-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 79060-88-1 ]

Fluorinated Building Blocks

Aryls

Trifluoromethyls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 79060-88-1 ]