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Structure of 556-96-7

Chemical Structure| 556-96-7

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Product Citations

Product Citations

Guo, Sheng ; Wu, Yifan ; Luo, Shao-Xiong Lennon ; Swager, Timothy M. ;

Abstract: Heterogenous catalysts with confined nanoporous catalytic sites are shown to have high activity and size selectivity. A solution-processable nanoporous organic polymer (1-BPy-Pd) catalyst displays high catalytic performance (TON > 200K) in the heterogeneous Suzuki–Miyaura coupling (SMC) reaction and can be used for the preparation of the intermediates in the synthesis of pharmaceutical agents. In comparison to the homogeneous catalyst analogue (2,2′-BPy)PdCl2, the heterogenous system offers size-dependent catalytic activity when bulkier substrates are used. Furthermore, the catalyst can be used to create catalytic impellers that simplify its use and recovery. We found that this system also works for applications in heterogenous Heck and nitroarenes reduction reactions. The metal-binding nanoporous polymer reported here represents a versatile platform for size-selective heterogeneous and recyclable catalysts.

Keywords: nanoporous organic polymer ; heterogeneous catalyst ; Suzuki−Miyaura coupling reaction ; size-selective reaction ; catalyst processing

Alternative Products

Product Details of [ 556-96-7 ]

CAS No. :556-96-7
Formula : C8H9Br
M.W : 185.06
SMILES Code : CC1=CC(Br)=CC(C)=C1
MDL No. :MFCD00000087
InChI Key :LMFRTSBQRLSJHC-UHFFFAOYSA-N
Pubchem ID :136357

Safety of [ 556-96-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 556-96-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 44.07
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.5
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.4
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.07
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

3.68
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.45
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.22

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.62
Solubility 0.0441 mg/ml ; 0.000238 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.08
Solubility 0.154 mg/ml ; 0.000833 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.02
Solubility 0.0175 mg/ml ; 0.0000946 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.01 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.18

Application In Synthesis of [ 556-96-7 ]

* 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.

  • Downstream synthetic route of [ 556-96-7 ]

[ 556-96-7 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 556-96-7 ]
  • [ 23351-91-9 ]
YieldReaction ConditionsOperation in experiment
34% Placing Compound A in an amount of 25.2 g (136 mmol) and KMnO4 in an amount of 86.1 g (544 mmol) into a flask, and the resultant solution was reacted in water for 9 hours under refluxing. After the reaction terminated, a precipitate was filtered and the filtrate was processed with 6N hydrochloric acid at room temperature. A deposit was washed with the use of 0. 1N hydrochloric acid and dried, resultantly obtaining 11.4 g of Intermediate B (yield: 34 percent).
  • 2
  • [ 556-96-7 ]
  • [ 7697-37-2 ]
  • [ 58530-13-5 ]
  • 3
  • [ 556-96-7 ]
  • [ 143-33-9 ]
  • [ 22445-42-7 ]
YieldReaction ConditionsOperation in experiment
86 - 90%Chromat. An oven dried screw cap test tube was charged with [NACN] (59 mg, [1.] 20 mmol), dried KI (33 mg, 0.199 mmol, 20 mol%) and Cul (20 mg, 0.105 mmol, 10 mol%), evacuated and backfilled with argon three times. [L-BROMO-3,] 5-dimethylbenzene [(135 PL,] 0.994 mmol), [NN'-DIMETHYLETHYLENEDIAMINE (110 GL,] 1.033 mmol) and anhydrous toluene (650 [RL)] were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at [110 C] for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 150 [PL] of n-dodecane as internal standard, 1 [ML] of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25 [C] for 10 min then the organic layer was washed with 1 mL of water and dried over [MGS04.] The GC analysis showed a conversion of 90% with a 86% yield of the title product, calculated vs internal standard.; An oven dried 100 mL three necked round bottom flask was charged, under positive pressure of argon, with [NACN] (2.04 g, 41.6 mmol) Cul (660 mg, 3.47 mmol, 10 mol%), KI (1.14 g, 6.87 mmol, 20 mol%), and anhydrous toluene (25 mL). [N, N'-] Dimethylethylenediamine (3.7 mL, 35 mmol) and 5-bromo-m-xylene (4.7 mL, 35 mmol) were added dropwise under mechanical stirring. The reaction mixture was stirred at 110 [C] for 24 h. The resulting suspension was allowed to reach room temperature, diluted with 30% aq ammonia (20 mL) and extracted with toluene [(2X10] mL). The combined organic phases were dried over [MGS04,] concentrated, and the residue was purified by distillation under reduced pressure (bp 100 [C] [&COMMAT; 10 ] Torr) to provide the desired product as a white crystalline solid (4.08 g, 90% yield). Mp [42-43 C] (lit. 42. [9 C,] See Birch, S. F.; Dean, R. A.; Fidler, F. A.; Lowry, R. A. [J.] [AM.] [CHEM. SOC.] 1949, [71,] [1362). IN] NMR (400 MHz, [CDC13] ; lit. See Nomura, Y.; Takeuchi, Y. [TETRAHEDROII] 1969, [25,] 3825): [8] 7.27 (s, 2H), 7.23 (s, 1H), 2.36 (s, 6H) ; 13C NMR (100 MHz, CDC13) : 139.4, 135.0, 130.1, 119.7, 112.4, 21.5 ; IR (neat, cm-1) : 2230,1605, 1378,907, 854,682. Anal. Calcd. for [C9H9N] : C, 82.41 ; H, 6.92 ; N, 10.68. Found: C, 82.11 ; H, 6.88, N, 10.52.
88%Chromat. An oven dried screw cap test tube was charged with [NACN] (140 mg, 2.857 mmol) dried KI (79 mg, 0.476 mmol, 20 mol%) and Cul (45 mg, 0. [236] mmol, 10 mol%), evacuated and backfilled with argon three times. Anhydrous toluene (1550 [P1), N, N'-] dimethylethylenediamine (255 [UL,] 2.395 mmol), [1-BROMO-3,] 5-dimethyl-benzene [(255] [UL,] 1.877 mmol), and benzyl alcohol (155 [P1,] 1.498 mmol) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at [110C] for 12 h. The resulting yellow color suspension was cooled to room temperature, 2 mL of ethyl acetate, 250 [UL] of n-dodecane as internal standard, 1 mL of ammonium hydroxide 30% and 1 mL of water were added. The mixture was stirred at [25C] for 10 min then the organic layer was washed with 1 mL of water and dried over [MGS04.] The GC analysis showed a conversion of 91% with a yield of the title product, calculated vs internal standard, of 88%.
An oven dried three necked 50 mL round bottom flask was charged with [NACN] (1.127 g, 23 mmol), dried KI (630 mg, 3. [8] mmol, 20 mol%), evacuated and backfilled with argon three times. Anhydrous toluene (10 [ML),] [L-BROMO-3,] 5-dimethylbenzene (2.6 mL, 19 mmol), were added under argon. In a separate oven dried flask, CuI (360 mg, 1.9 mmol, 10 mol%) was mixed under stirring with N, N'-dimethylethylenediamine (2 mL, 19 mmol). The resulting dark-green mixture was diluted with anhydrous toluene (2 mL) and added, under vigorous stirring at [25C,] to the mixture containing aryl bromide. The obtained reaction mixture was magnetically stirred under reflux in an argon atmosphere, at [110 C] for 36 h. The resulting yellow suspension was cooled to room temperature. 50 iL of the mixture were diluted with 0.5 mL of ethyl acetate and treated with 0.5 mL of ammonium hydroxide (30%) and water. The resulting organic layer was washed with 1 mL of water and dried over MgS04. The GC analysis showed essentially complete consumption of the starting material, and formation of the title compound (confirmed by GC-MS).
An oven dried screw cap test tube was charged with [NACN] (73 mg, [1.] 489 mmol), dried KI (42 mg, 0.253 mmol, 20 mol%) and Cul (24 mg, 0.126 mmol, 10 mol%), evacuated and backfilled with argon three times. [L-BROMO-3,] 5-dimethylbenzene (170 [PL,] 1.251 mmol), [N, N'-DIMETHYLETHYLENEDIAMINE (135, UL,] 1.271 mmol) and anhydrous benzotrifluoride [(825] muL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at [102 C FOR] 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at [25 C] for 10 min, then the organic layer was washed with 1 mL of water and dried over [MGS04.] The GC analysis showed complete consumption of the starting material, and formation of the title compound (confirmed by GC-MS).
An oven dried screw cap test tube was charged with [NACN] [(88] mg, 1.796 mmol), dried NaI (44 mg, 0.294 mmol, 20 mol%) and Cul (28 mg, 0.147 mmol, 10 mol%), evacuated and backfilled with argon three times. [L-BROMO-3,] 5-dimethylbenzene [(200, UL,] 1.472 mmol), [N, N'-DIMETHYLETHYLENEDIAMINE (160, UL,] 1.503 mmol) and anhydrous toluene (1 [ML)] were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at [110 C] for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at [25 C] for 10 min then the organic layer was washed with 1 mL of water and dried over [MGS04.] The GC analysis showed essentially complete consumption of the starting material, and formation of the title compound (confined by GC- MS).

  • 4
  • [ 556-96-7 ]
  • K4Fe(CN)6 [ No CAS ]
  • [ 22445-42-7 ]
  • 5
  • [ 556-96-7 ]
  • [ 557-21-1 ]
  • [ 22445-42-7 ]
  • 6
  • [ 120-72-9 ]
  • aq ammonia [ No CAS ]
  • [ 556-96-7 ]
  • [ 110-70-3 ]
  • [ 22445-42-7 ]
YieldReaction ConditionsOperation in experiment
15% With potassium cyanide; CuI; In dodecane; ethyl acetate; toluene; Example 216 3,5-Dimethylbenzonitrile from 5-bromo-m-xylene and Potassium Cyanide using N,N'-dimethylethylenediamine as Ligand A Schlenk tube was charged with CuI (19.5 mg, 0.102 mmol, 20 mol %), KCN (78 mg, 1.20 mmol), evacuated, backfilled with Ar. N,N'-Dimethylethylenediamine (21.5 muL, 0.202 mmol, 20 mol %), 5-bromo-m-xylene (136 muL, 1.00 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110 C. for 24 h. Dodecane (internal GC standard, 230 muL), ethyl acetate (2 mL), and 30% aq ammonia (1 mL) were added. A 0.1 mL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide a 15% yield of 3,5-dimethylbenzonitrile.
  • 8
  • [ 556-96-7 ]
  • [ 544-92-3 ]
  • [ 22445-42-7 ]
  • 10
  • potassiumhexacyanoferrate(II) trihydrate [ No CAS ]
  • [ 556-96-7 ]
  • [ 22445-42-7 ]
  • 12
  • [ 556-96-7 ]
  • [ 22445-42-7 ]
  • [ 2622-05-1 ]
  • [ 1285695-66-0 ]
  • 13
  • [ 556-96-7 ]
  • [ 58530-13-5 ]
YieldReaction ConditionsOperation in experiment
29% With potassium permanganate; water; at 80℃; for 2.25h; l-bromo-3,5-dimethylbenzene (15 g, 81 mmol, 1.0 eq) in a mixture of pyridine (133 mL) and H20 (83 mL) was heated to 80C. KMn04 (25.6 g, 162 mmol, 2.0 eq) was added in portions over 45 min. After the addition was completed, heating was continued at 80C for 1.5 h. The hot solution was then filtered, and the filtrate was acidified by addition of concentrated hydrochloric acid. The aqueous solution was extracted with EtOAc and the combined organic extracts washed with water and brine, dried (Na2SC>4), filtered and evaporated in vacuo. The residue was purified by column chromatography (CH2C12: MeOH, 80: 1 to 40: 1) to give the title compound as a white solid (5.2 g, 29 %)LC-MS: m z 212.9, 215 [M+H]+ 1H NMR (400 MHz, MeOD) delta 7.91 (s, 1H), 7.79 (s, 1H), 7.57 (s, 1H), 2.38 (s, 3H).
  • 15
  • [ 556-96-7 ]
  • potassium ferrocyanide [ No CAS ]
  • [ 22445-42-7 ]
YieldReaction ConditionsOperation in experiment
94% With 5,5?-(1,2-phenylene)bis(1H-tetrazole); copper(I) iodide; caesium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 130℃; for 15h;Inert atmosphere; General procedure: A mixture of copper salt (0.3 mmol) and 2 (0.8 mmol) in DMF (2 mL)was stirred at room temperature under a dry nitrogen atmospherefor 10 min to give a homogeneous solution. Next the aryl bromide(1 mmol), base (1.0 mmol), KI (0.5 mmol), K4Fe(CN)6 (0.22 mmol)and DMF (2 mL) were added and the mixture stirred at 130 C for 10 h(Table 2). After completion (as monitored by TLC), H2O (15 mL) was added and the organic layer was extracted with EtOAc (3 × 15 mL),washed with brine (15 mL), dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by columnchromatography. All the products are known and were characterisedby IR, NMR and melting points and their spectroscopic data identicalto that reported in the literature.
93% With caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 8h;Inert atmosphere; Sealed tube; General procedure: Under a dry nitrogen atmosphere, a mixture of aryl bromide(1.0 mmol), K4Fe(CN)6 (0.22 mmol), base (1.0 mmol) and Pd(0)-EGCG-CF (2.0 mol%) in DMF (5 mL) was stirred at 130 C for 8 h (Table 2). After completion (as monitoredby TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography. All of the desired product(s) were characterized by comparison of their physical data with those of known compounds [4,5c,7]. The formation of aryl nitriles was confirmed by IR spectra, which showed one characteristic peak for the CN stretching band between 2225-2360 cm-1.
91% With copper(II) acetate monohydrate; sodium carbonate; 1,3-phenylene-bis-(1H)-tetrazole; potassium iodide; In N,N-dimethyl-formamide; at 130℃; for 8h;Inert atmosphere; General procedure: Under a dry nitrogen atmosphere, a mixture of copper acetate (0.2 mmol) and 2 (0.2 mmol) in DMF (2 mL) was stirred at room temperature for 10 min to give a homogeneous solution. Next the aryl halide (1 mmol), base (0.25mmol), KI (0.5 mmol), K4Fe(CN)6 (0.22 mmol) and DMF (2mL) were added and the mixture was stirred at 130 C for 8h (Table 2). The reaction mixture was cooled at room temperature,diluted with H2O (15 mL), extracted with ethylacetate (3 15 mL), washed with brine (15 mL) and dried(MgSO4). The reaction mixture was filtered. The filtrate was evaporated under reduced pressure and the residue was subjected to gel permeation chromatography to afford pure products. The physical data (mp, IR, NMR) of the products were found to be identical with those reported in the literature[6-11,14,15].
88% With copper(l) iodide; 3,3'-(1,4-phenylene)bis-(2-imino-2,3-dihydrobenzo[d]-oxazol-5-ol); caesium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 130℃; for 8h;Inert atmosphere; General procedure: To a mixture of copper salt (0.3 mmol) and ligand 3 (0.8mmol) in DMF (2.5 mL), aryl halide (1.0 mmol), base (0.25mmol), KI (0.5 mmol), K4Fe(CN)6 (0.2 mmol) and DMF (2.5 mL) were added and the mixture was vigorously stirredat 130 C for 8 h under a dry nitrogen atmosphere. Aftercompletion (as monitored by TLC with EtOAc and nhexane),H2O was added and the organic layer was extractedwith EtOAc, washed with brine, dried over MgSO4, filteredand evaporated under reduced pressure. The residue waspurified by column chromatography. The purity of the compoundswas checked by 1H NMR and yields are based onaryl bromide. All the products are known and the spectroscopicdata (FT-IR and NMR) and melting points were consistentwith those reported in the literature [3-8].
78% With C30H24N3OPPd; triethylamine; In N,N-dimethyl-formamide; at 100℃; for 24h; General procedure: IIn a round bottom flask a mixture of aryl halides (5.5mmol),K4Fe(CN)6 (5.5mmol), palladium catalyst, 2a (0.02 mmol), triethylamine (10mmol) and 10 mL DMF was taken and the mixture wasstirred for 24 h under air at 100 C. After reactionwas over the solventwas evaporated and the productwas poured intowater and extractedwith diethyl ether, dried over Na2SO4 and passed through 12// silicacolumn (60-120mesh).Upon evaporation of the ether, pure productswere obtained. The isolated yields of the products obtained fromall the reactions were determined after isolation and characterizedby IR spectroscopy (Fig. S-21) since cyano substituent(mCN 2230 cm1) exhibit very characteristic stretching band.

  • 16
  • [ 556-96-7 ]
  • [ 526-08-9 ]
  • C23H22N4O2S [ No CAS ]
  • 17
  • [ 556-96-7 ]
  • [ 198904-31-3 ]
  • C54H68N6O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
146.1 mg With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 35℃; for 72h;Inert atmosphere; Glovebox; General procedure: Unless otherwise stated, in an Argon filled glove-box a crimp-cap microwave vial equipped with a magnetic stirring bar was charged with the appropriate cyclometalated Ru(ll)-catalyst (like Ru1-Ru46, from 3 mol % to 10 mol %), KOAc (5.9 mg, 0.06 mmol, 30 mol %), K2CO3 (2.0 - 4.0 equiv.), the appropriate DG-containing arene (like N1-N12, 0.20 mmol, 1.0 equiv.), the appropriate (hetero)aryl (pseudo)halide (like X1-X42, 0.2 mmol, 1.0 equiv) and /V-methyl-2- pyrrolidone (NMP) (200 pL, 1 M). The vial was capped and stirred at 35 C for 24 hours. Upon completion, the crude mixture was loaded on a silica gel column and purified by flash chromatography
  • 18
  • [ 556-96-7 ]
  • [ 75-05-8 ]
  • [ 22445-42-7 ]
  • 19
  • [ 630-18-2 ]
  • [ 556-96-7 ]
  • [ 22445-42-7 ]
YieldReaction ConditionsOperation in experiment
70% General procedure: To a solution of 4-bromobiphenyl 1a (3.0 mmol, 699.3 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol, 1.55 M in hexane, 2.87 mL) at 50 C. The obtained mixture was stirred for 30 min at 50 C under an argon atmosphere. Pivalonitrile (6.0 mmol, 498.8 mg) in THF (2.0 mL) was added to the mixture at 50 C and the obtained mixture was stirred for 30 min in the temperature range of 50 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 4-cyanobiphenyl 2a (451.6 mg, 84%).
 

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A125625 [1611-92-3]

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A163712 [60956-23-2]

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A487852 [2725-82-8]

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A205299 [90267-03-1]

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