[ CAS No. 5123-13-7 ] {[proInfo.proName]}

Name: 5123-13-7|5,5-Dimethyl-2-phenyl-1,3,2-dioxaborinane|98%
Brand: Ambeed
SKU: A101923
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2D 3D

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Quality Control of [ 5123-13-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5123-13-7 ]

SDS Specification

Alternatived Products of [ 5123-13-7 ]

Product Details of [ 5123-13-7 ]

CAS No. :	5123-13-7	MDL No. :	MFCD05663851
Formula :	C₁₁H₁₅BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FQMSNYZDFMWLGC-UHFFFAOYSA-N
M.W :	190.05	Pubchem ID :	11788741
Synonyms :

Calculated chemistry of [ 5123-13-7 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.45
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	57.78
TPSA :	18.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.86
Log Po/w (WLOGP) :	1.45
Log Po/w (MLOGP) :	1.46
Log Po/w (SILICOS-IT) :	1.59
Consensus Log Po/w :	1.47

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.07
Solubility :	0.161 mg/ml ; 0.000849 mol/l
Class :	Soluble
Log S (Ali) :	-2.91
Solubility :	0.236 mg/ml ; 0.00124 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.51
Solubility :	0.0582 mg/ml ; 0.000306 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.9

Safety of [ 5123-13-7 ]

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 [ 5123-13-7 ]

* 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 [ 5123-13-7 ]
Downstream synthetic route of [ 5123-13-7 ]

[ 5123-13-7 ] Synthesis Path-Upstream 1~2

1
[ 52200-48-3 ]
[ 5123-13-7 ]
[ 1008-89-5 ]
[ 91182-50-2 ]

Reference： [1] Organometallics, 2017, vol. 36, # 22, p. 4363 - 4366

2
[ 5123-13-7 ]
[ 75-98-9 ]
[ 5669-14-7 ]

Reference： [1] Journal of the American Chemical Society, 2007, vol. 129, # 12, p. 3510 - 3511

[ 5123-13-7 ] Synthesis Path-Downstream 1~88

1
[ 17408-14-9 ]
[ 5123-13-7 ]
1-(3-trifluoromethyl-biphenyl-2-yl)-ethanone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 1698 - 1699
[2]Journal of the American Chemical Society,2005,vol. 127,p. 5936 - 5945
[3]Organic Syntheses,2010,vol. 87,p. 209 - 217

2
[ 5123-13-7 ]
[ 98-86-2 ]
[ 2142-66-7 ]
1-[1,1';3',1"]terphenyl-2'-yl-ethanone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 5936 - 5945
[2]Journal of Organic Chemistry,2019,vol. 84,p. 12975 - 12982
[3]Journal of the American Chemical Society,2003,vol. 125,p. 1698 - 1699
[4]Journal of the American Chemical Society,2005,vol. 127,p. 5936 - 5945
[5]Organic Letters,2010,vol. 12,p. 5318 - 5321
[6]Organic Letters,2010,vol. 12,p. 5318 - 5321
[7]Chemistry - A European Journal,2013,vol. 19,p. 10378 - 10387

3
[ 10045-45-1 ]
[ 5123-13-7 ]
1-ethyl-3-phenyl-1,3-dihydro-2H-benzo[d]imidazol-2-one [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 3863 - 3865

4
[ 1138-52-9 ]
[ 5123-13-7 ]
[ 62787-21-7 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 3863 - 3865

5
[ 6161-64-4 ]
[ 5123-13-7 ]
[ 223785-68-0 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 2706 - 2707

6
[ 2040-04-2 ]
[ 5123-13-7 ]
1-[1,1';3',1"]terphenyl-2'-yl-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene for 1h; Heating;
45 %Chromat.	With styrene; carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); cesium fluoride In toluene at 120℃; for 0.5h;
94 %Chromat.	With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 125℃; for 20h; Schlenk technique;	V. General Procedure for C-O Diarylation of 2’,6’-Dimethoxyacetophenone (6) General procedure: To an oven-dried 20 mL Schlenk tube containing a magnetic stirring bar were added 2’,6’-dimethoxyacetophenone (6) (0.5mmol), arylboronate 2 (1.5 mmol), RuH2(CO)(PPh3)3 (0.05 mmol), and 0.5 mL of dry toluene. The resulting mixture washeated at 125 °C for 20 h and cooled to room temperature. Hexacosane was added as an internal standard to the mixture,which was then analyzed by GC. The crude material was passed through a basic aluminium oxide column to remove theremaining arylboronate. Further purification of the product was performed by silica gel column chromatography(hexane:AcOEt = 20:1). Diarylation Product 7a Following the general procedure, diarylation product 7a was obtained as a white solid. The analytical datafor 7a are in good agreement with those reported in literature.3

Reference： [1]Kakiuchi, Fumitoshi; Usui, Mayumi; Ueno, Satoshi; Chatani, Naoto; Murai, Shinji [Journal of the American Chemical Society, 2004, vol. 126, # 9, p. 2706 - 2707]
[2]Kondo, Hikaru; Kochi, Takuya; Kakiuchi, Fumitoshi [Organic Letters, 2017, vol. 19, # 4, p. 794 - 797]
[3]Izumoto, Akiko; Kondo, Hikaru; Kochi, Takuya; Kakiuchi, Fumitoshi [Synlett, 2017, vol. 28, # 19, p. 2609 - 2613]

7
[ 13185-18-7 ]
[ 5123-13-7 ]
8-phenyl-3,4-dihydro-2H-naphthalen-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 2706 - 2707

8
[ 2977-45-9 ]
[ 5123-13-7 ]
2,2-dimethyl-8-phenyl-3,4-dihydro-2H-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 5936 - 5945

9
[ 5123-13-7 ]
[ 88-10-8 ]
[ 1696-17-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bis-triphenylphosphine-palladium(II) chloride; cesium fluoride In tetrahydrofuran at 80℃; for 16h;

Reference： [1]Lysen, Morten; Kelleher, Susan; Begtrup, Mikael; Kristensen, Jesper Langgaard [Journal of Organic Chemistry, 2005, vol. 70, # 13, p. 5342 - 5343]

10
[ 67-56-1 ]
[ 5123-13-7 ]
[ 1184-88-9 ]
[ 14248-22-7 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 3510 - 3511

11
[ 5123-13-7 ]
[ 75-98-9 ]
[ 5669-14-7 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 3510 - 3511

12
[ 66107-29-7 ]
[ 5123-13-7 ]
[ 613-37-6 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 10596 - 10602

13
[ 6257-03-0 ]
[ 5123-13-7 ]
[ 1244031-97-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 5860 - 5866

14
[ 6257-03-0 ]
[ 5123-13-7 ]
[ 68-12-2 ]
[ 1244032-02-7 ]
[ 1244031-97-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 5860 - 5866

15
[ 5580-79-0 ]
[ 5123-13-7 ]
[ 1244031-96-6 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 5860 - 5866

16
[ 5580-79-0 ]
[ 5123-13-7 ]
[ 68-12-2 ]
[ 1244032-01-6 ]
[ 1244031-96-6 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 5860 - 5866

17
[ 570-02-5 ]
[ 5123-13-7 ]
[ 64461-92-3 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 677 - 679

18
[ 4292-19-7 ]
[ 5123-13-7 ]
[ 599-91-7 ]
[ 103-65-1 ]
[ 123-01-3 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 3904 - 3907

19
[ 3742-75-4 ]
[ 5123-13-7 ]
[ 1081-75-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere;

Reference： [1]Yang, Chu-Ting; Zhang, Zhen-Qi; Liu, Yu-Chen; Liu, Lei [Angewandte Chemie - International Edition, 2011, vol. 50, # 17, p. 3904 - 3907]

20
[ 10157-76-3 ]
[ 5123-13-7 ]
[ 123-01-3 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 3904 - 3907

21
[ 3839-35-8 ]
[ 5123-13-7 ]
[ 1077-16-3 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 3904 - 3907

22
[ 5123-13-7 ]
[ 143-15-7 ]
[ 599-91-7 ]
[ 103-65-1 ]
[ 123-01-3 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 3904 - 3907

23
[ 5123-13-7 ]
[ 599-91-7 ]
[ 103-65-1 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 3904 - 3907

24
[ 5123-13-7 ]
[ 599-91-7 ]
[ 112-52-7 ]
[ 103-65-1 ]
[ 123-01-3 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 3904 - 3907

25
[ 288-47-1 ]
[ 5123-13-7 ]
[ 1826-11-5 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 6321 - 6325

26
[ 1006-68-4 ]
[ 5123-13-7 ]
[ 92-71-7 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 6321 - 6325

27
[ 1826-13-7 ]
[ 5123-13-7 ]
[ 3704-40-3 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 6321 - 6325

28
[ 13670-99-0 ]
[ 5123-13-7 ]
1-[1,1';3',1"]terphenyl-2'-yl-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); cesium fluoride; ethenyltrimethylsilane; In toluene; at 130℃; for 24h;	General procedure: To a 20-mL J-Young tube was added ruthenium complex 3 (0.2 mmol) and arylboronate 2 (2 mmol). n-Eicosane (0.4 mmol) was also added when the yield was determined by GC analysis. The J-Young tube was brought into a glove box filled with nitrogen, and cesium floride, trimethylvinylsilane, toluene, and fluorinated aromatic ketone 1 was introduced into the tube. The J-Young tube was then taken out of the glove box and heated at 130 C in an oil bath for 24 h. GC analysis was performed after the reaction mixture was cooled to rt. To isolate the arylation product, volatile materials were removed from the mixture by rotary evaporator, and the resulting material was passed through a short column of basic alumina using dichloromethane to remove unreacted arylboronate 2. The resulting material was concentrated again by rotary evaporator and then passed through a silica gel column using hexane with ethyl acetate as eluents. Further purification by Kugelrohr distillation provided the arylation product in a pure form.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5888 - 5890

29
[ 3038-48-0 ]
[ 5123-13-7 ]
[ 1214390-18-7 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 18183 - 18193

30
[ 1131-33-5 ]
[ 5123-13-7 ]
[ 3558-69-8 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4292 - 4295

31
[ 1003-67-4 ]
[ 5123-13-7 ]
[ 3475-21-6 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4292 - 4295

32
[ 1131-61-9 ]
[ 5123-13-7 ]
[ 26274-35-1 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 4292 - 4295

33
[ 103-82-2 ]
[ 599-67-7 ]
[ 528-75-6 ]
[ 60-12-8 ]
[ 104-94-9 ]
[ 126-30-7 ]
[ 98-80-6 ]
[ 530-48-3 ]
[ 354538-06-0 ]
[ 102-20-5 ]
[ 5123-13-7 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 9401 - 9404

34
[ 1667-11-4 ]
[ 5123-13-7 ]
[ 613-42-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With 1-methyl-2-azepanone; copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione; lithium tert-butoxide at 60℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Sun, Yan-Yan; Yi, Jun; Lu, Xi; Zhang, Zhen-Qi; Xiao, Bin; Fu, Yao [Chemical Communications, 2014, vol. 50, # 75, p. 11060 - 11062]

35
[ 5123-13-7 ]
[ 77211-75-7 ]
benzyl 4-benzyl-4-hydroxypiperidine-1-carboxylate [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 2388 - 2391

36
4-benzoylphenyl diisopropylcarbamate [ No CAS ]
[ 5123-13-7 ]
[ 2128-93-0 ]

Yield	Reaction Conditions	Operation in experiment
31%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,3-bis(adamantan-2-yl)imidazolin-2-yliden chloride; sodium ethanolate In toluene at 130℃; for 20h; Sealed tube; Inert atmosphere;	5. Typical Procedure for Rh-catalyzed Cross-coupling of Aryl Carbamates (Entry1 in Table 3) General procedure: [RhCl(cod)]2 (7.4 mg, 0.015 mmol), I(2-Ad)·HCl (22 mg, 0.060 mmol), NaOEt (41 mg,0.60 mmol) and toluene (0.40 mL) were added to a 10 mL sample vial with a Teflonsealed screwcap in a glovebox filled with nitrogen, and the resulting mixture was stirredfor 10 min. Naphthalen-2-yl diisopropylcarbamate (10, 81 mg, 0.30 mmol),5,5-dimethyl-2-(p-tolyl)-1,3,2-dioxaborinane (4b, 92 mg, 0.45 mmol) and toluene (0.60mL) were then added to the vial, and the resulting mixture was sealed in the vessel andheated at 130 °C for 20 h on an aluminum block. The mixture was then cooled to roomtemperature and purified directly by flash column chromatography over silica gel(eluent: hexane/EtOAc = 10:1) to give 2-(p-tolyl)naphthalene (38, 64 mg, 98%) as awhite solid.

Reference： [1]Nakamura, Keisuke; Yasui, Kosuke; Tobisu, Mamoru; Chatani, Naoto [Tetrahedron, 2015, vol. 71, # 26-27, p. 4484 - 4489]

37
C₁₉H₂₃NO₂ [ No CAS ]
[ 5123-13-7 ]
[ 92-06-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 1,3-bis(adamantan-2-yl)imidazolin-2-yliden chloride; sodium ethanolate In toluene at 130℃; for 20h; Sealed tube; Inert atmosphere;	5. Typical Procedure for Rh-catalyzed Cross-coupling of Aryl Carbamates (Entry1 in Table 3) General procedure: [RhCl(cod)]2 (7.4 mg, 0.015 mmol), I(2-Ad)·HCl (22 mg, 0.060 mmol), NaOEt (41 mg,0.60 mmol) and toluene (0.40 mL) were added to a 10 mL sample vial with a Teflonsealed screwcap in a glovebox filled with nitrogen, and the resulting mixture was stirredfor 10 min. Naphthalen-2-yl diisopropylcarbamate (10, 81 mg, 0.30 mmol),5,5-dimethyl-2-(p-tolyl)-1,3,2-dioxaborinane (4b, 92 mg, 0.45 mmol) and toluene (0.60mL) were then added to the vial, and the resulting mixture was sealed in the vessel andheated at 130 °C for 20 h on an aluminum block. The mixture was then cooled to roomtemperature and purified directly by flash column chromatography over silica gel(eluent: hexane/EtOAc = 10:1) to give 2-(p-tolyl)naphthalene (38, 64 mg, 98%) as awhite solid.

Reference： [1]Nakamura, Keisuke; Yasui, Kosuke; Tobisu, Mamoru; Chatani, Naoto [Tetrahedron, 2015, vol. 71, # 26-27, p. 4484 - 4489]

38
[ 348-51-6 ]
[ 5123-13-7 ]
[ 321-60-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium phosphate tribasic hydrate; Ni<SUP>II</SUP>Cl(1-naphthyl)(tricyclohexylphosphine)<SUB>2</SUB>; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 1h; Inert atmosphere; Glovebox; Sealed tube;	Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 °C; General Procedure 2 General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 °C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 °C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized.

Reference： [1]Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil [Synthesis, 2016, vol. 48, # 17, p. 2795 - 2807]

39
[ 5123-13-7 ]
2-fluorophenyl methanesulfonate [ No CAS ]
[ 321-60-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium phosphate tribasic hydrate; Ni<SUP>II</SUP>Cl(1-naphthyl)(tricyclohexylphosphine)<SUB>2</SUB>; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 1h; Inert atmosphere; Glovebox; Sealed tube;	Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 °C; General Procedure 2 General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 °C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 °C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized.

Reference： [1]Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil [Synthesis, 2016, vol. 48, # 17, p. 2795 - 2807]

40
[ 348-52-7 ]
[ 5123-13-7 ]
[ 321-60-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium phosphate tribasic hydrate; Ni<SUP>II</SUP>Cl(1-naphthyl)(tricyclohexylphosphine)<SUB>2</SUB>; tricyclohexylphosphine In tetrahydrofuran at 23℃; for 16h; Inert atmosphere; Glovebox; Sealed tube;	Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 °C; General Procedure 2 General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 °C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 °C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized.

Reference： [1]Malineni, Jagadeesh; Jezorek, Ryan L.; Zhang, Na; Percec, Virgil [Synthesis, 2016, vol. 48, # 17, p. 2795 - 2807]

41
[ 625-98-9 ]
[ 5123-13-7 ]
[ 2367-22-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 1h;Inert atmosphere; Glovebox; Sealed tube;	General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized.

Reference： [1]Synthesis,2016,vol. 48,p. 2795 - 2807

42
[ 57606-63-0 ]
[ 5123-13-7 ]
[ 2367-22-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 1h;Inert atmosphere; Glovebox; Sealed tube;	General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized.

Reference： [1]Synthesis,2016,vol. 48,p. 2795 - 2807

43
[ 1121-86-4 ]
[ 5123-13-7 ]
[ 2367-22-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 16h;Inert atmosphere; Glovebox; Sealed tube;	Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized.

Reference： [1]Synthesis,2016,vol. 48,p. 2795 - 2807

44
[ 352-33-0 ]
[ 5123-13-7 ]
[ 324-74-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 1h;Inert atmosphere; Glovebox; Sealed tube;	General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized.

Reference： [1]Synthesis,2016,vol. 48,p. 2795 - 2807
[2]ACS Catalysis,2021,vol. 11,p. 3856 - 3866

45
[ 5123-13-7 ]
[ 72358-72-6 ]
[ 324-74-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 1h;Inert atmosphere; Glovebox; Sealed tube;	General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized.

Reference： [1]Synthesis,2016,vol. 48,p. 2795 - 2807

46
[ 352-34-1 ]
[ 5123-13-7 ]
[ 324-74-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium phosphate tribasic hydrate; NiIICl(1-naphthyl)(tricyclohexylphosphine)2; tricyclohexylphosphine; In tetrahydrofuran; at 23℃; for 15h;Inert atmosphere; Glovebox; Sealed tube;	General procedure: Cross-Coupling of ortho-, meta-, and para-Substituted, Electron-Rich and Electron-Deficient Aryl Halides and Aryl Mesylates with Aryl Neopentylglycolboronates Catalyzed by NiIICl(1-naph-thyl)(PCy3)2/PCy3 in Anhydrous THF at 23 C; General Procedure 2In an oven-dried test tube charged with a Teflon coated stirring barwere added aryl halide or aryl mesylate (0.3 mmol), aryl neopentyl-glycolboronates (0.315 mmol), K3PO4(H2O)3.2 (191.00 ± 1.00 mg, 0.9mmol), and NiIICl(1-naphthyl)(PCy3)2 (11.73 ± 0.0510 mg, 0.015mmol, 5% catalyst loading). The test tube was brought into a N2 filledglove box (moisture level <2 ppm) through three degassing cycles andPCy3 (8.4 mg, 0.03 mmol, 10% loading) ligand was added. Distilled sol-vent (1 mL) was added inside the glove box and the test tube wassealed by a rubber septum and left stirring at 23 C. A sample was tak-en by syringe and transferred outside the glove box. The sample wasdiluted by distilled THF (0.2 mL) and filtered through a short columnof Al2O3. The filtrate was concentrated and the GC analysis was car-ried out. The reaction mixture was diluted with CH2Cl2 (2 mL), filteredthrough a layer of Al2O3, and washed with CH2Cl2 (3 1 mL). The fil-trate was collected and concentrated under vacuum. The crude prod-uct was purified by column chromatography on silica gel with EtO-Ac/hexane mixture as eluent. The reductive elimination side-productwas also isolated and characterized.

Reference： [1]Synthesis,2016,vol. 48,p. 2795 - 2807

47
[ 5123-13-7 ]
[ 2142-66-7 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 4186 - 4189

48
[ 392-56-3 ]
[ 5123-13-7 ]
[ 784-14-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With [Ni₂(1,3-diisopropylimidazolin-2-ylidene)₄(cod)]; cesium fluoride In toluene at 100℃; for 18h; Schlenk technique; Glovebox; Inert atmosphere;

Reference： [1]Zhou, Jing; Berthel, Johannes H. J.; Kuntze-Fechner, Maximilian W.; Friedrich, Alexandra; Marder, Todd B.; Radius, Udo [Journal of Organic Chemistry, 2016, vol. 81, # 13, p. 5789 - 5794]

49
[ 116-14-3 ]
[ 98-08-8 ]
[ 455-13-0 ]
[ 5123-13-7 ]
1,1,2,2,-tetrafluoro-1-(p-trifluoromethylphenyl)-2-phenylethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%		General procedure: CuOtBu (2.7 mg, 0.02 mmol), 1, 10-phenanthroline (3.6 mg, 0.02 mmol), arylboronic acid ester (0.024 mmol, 1.2 eq), and a,a,a-trifluorotoluene (2.4 pL, 0.02 mmol; as an internal standard for ?9F NMR) were mixed in THF/THF-d8 (v/v?=4/1) solvent in an NMR tube under a nitrogen atmosphere. TFE was pressurized to 3.5 atm, and the respective reactions were allowed to proceed. After the unreacted TFE was degassed, 4-trifluoromethyl iodobenzene (6.5 mg, 0.024 mmol, 1.2 eq) was added thereto and heated at 60 C. for 4 hours. The yield of each title compound was calculated from?9F NMR. The procedure of method C was repeated using 5,5- dimethyl-2-phenyl-1 ,3,2-dioxaborinane (4.6 mg) as a substrate, thereby giving the title compound (a compound same as the title compound of Example 2-3) at a yield of 93%.

Reference： [1]Patent: US2016/214999,2016,A1 .Location in patent: Paragraph 0417; 0418; 0419

50
[ 2040-04-2 ]
[ 5123-13-7 ]
1-(3-methoxy[1,1′-biphenyl]-2-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With styrene; carbonylchlorohydridobis(triisopropylphosphine)ruthenium(II); cesium fluoride In toluene at 80℃; for 0.25h; Glovebox; Inert atmosphere; Sealed tube;
7%	With styrene; tri-tert-butyl phosphine; (Carbonyl)dichloro(p-cymol)ruthenium(II); cesium fluoride In toluene at 100℃; for 1h; Sealed tube; Glovebox;

Reference： [1]Kondo, Hikaru; Kochi, Takuya; Kakiuchi, Fumitoshi [Organic Letters, 2017, vol. 19, # 4, p. 794 - 797]
[2]Kondo, Hikaru; Kochi, Takuya; Kakiuchi, Fumitoshi [Chemistry - A European Journal, 2020, vol. 26, # 8, p. 1737 - 1741]

51
[ 2040-04-2 ]
[ 5123-13-7 ]
1-(3-methoxy[1,1′-biphenyl]-2-yl)ethan-1-one [ No CAS ]
1-[1,1';3',1"]terphenyl-2'-yl-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 78% 2: 17%	With styrene; (Carbonyl)dichloro(p-cymol)ruthenium(II); cesium fluoride; tris(1-methylethyl)phosphine In toluene at 100℃; for 1h; Sealed tube; Glovebox;
1: 63% 2: 8%	With styrene; (Carbonyl)dichloro(p-cymol)ruthenium(II); cesium fluoride; tri(m-tolyl)phosphine In toluene at 100℃; for 1h; Sealed tube; Glovebox;
1: 50 %Chromat. 2: 19 %Chromat.	With styrene; C₃₉H₃₄O₃P₂Ru; cesium fluoride In toluene at 120℃; for 0.5h;

1: 61 %Chromat. 2: 9 %Chromat.

With styrene; C₃₉H₇₀O₃P₂Ru; cesium fluoride In toluene at 120℃; for 0.5h;

Reference： [1]Kondo, Hikaru; Kochi, Takuya; Kakiuchi, Fumitoshi [Chemistry - A European Journal, 2020, vol. 26, # 8, p. 1737 - 1741]
[2]Kondo, Hikaru; Kochi, Takuya; Kakiuchi, Fumitoshi [Chemistry - A European Journal, 2020, vol. 26, # 8, p. 1737 - 1741]
[3]Kondo, Hikaru; Kochi, Takuya; Kakiuchi, Fumitoshi [Organic Letters, 2017, vol. 19, # 4, p. 794 - 797]
[4]Kondo, Hikaru; Kochi, Takuya; Kakiuchi, Fumitoshi [Organic Letters, 2017, vol. 19, # 4, p. 794 - 797]

52
[ 447-60-9 ]
[ 5123-13-7 ]
6-phenyl-2-(trifluoromethyl)benzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6503 - 6510

53
[ 447-60-9 ]
[ 5123-13-7 ]
4,6-diphenyl-2-(trifluoromethyl)benzonitrile [ No CAS ]
6-phenyl-2-(trifluoromethyl)benzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6503 - 6510

54
[ 25753-25-7 ]
[ 5123-13-7 ]
2,6-bis(trifluoromethyl)-4-phenylbenzonitrile [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6503 - 6510

55
[ 13472-85-0 ]
[ 5123-13-7 ]
[ 53698-47-8 ]