Thieme journal awardees - Where are they now? on cobalt-catalyzed biaryl coupling reactions

Synlett

Volumn , Issue 18, 2009, Pages 2919-2923

  Mayer, Matthias ^a   Czaplik, Waldemar Maximilian ^a   Jacobi Von Wangelin, Axel ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Biaryls; Cross coupling; Dimerizations; Domino reactions; Grignard reactions

Indexed keywords

BROMINE DERIVATIVE; COBALT; COBALT CHLORIDE; LIGAND; OXIDIZING AGENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; DIMERIZATION; EXPERIMENT; GRIGNARD REACTION; SCIENTIFIC LITERATURE;

EID: 72049084259     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218013     Document Type: Article

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61. General Procedure A 10 mL flask was charged with Mg ribbons (74 mg, 3.0 mmol), fitted with a rubber septum, and purged with argon (1 min). Dry THF (4 mL) and the arylbromide (2.5 mmol) were added via a syringe. The solution was stirred at r.t. for 13 h under argon. Cooled to 0 C, a solution of CoCl2 (16.1 mg, 0.12 mmol, 5 mol%) in dry THF (6 mL) was added. Synthetic air (20 mL/min) was added through a needle to the solution. After 0.53 h, the reaction was quenched with sat. aq NH4Cl (5 mL), extracted with EtOAc (3 × The combined organic phases were dried (Na2SO4), concentrated, and subjected to flash chromatography (cyclohexeneEtOAc). New Compounds 3′,3′′ Difluoro[1,1′:4,1′′:4′,1′′′] quarter-phenyl (2n): mp 182 C. 1H NMR (300 MHz, CDCl3): d = 7.75 (d, 4 H, J = 6 Hz), 7.657.05 (m, 12 H). 13C NMR (75 MHz, CDCl3): d = 160.0 (d, J = 246 Hz), 140.4 (d, J = 6.8 Hz), 135.3 (d, J = 12.4 Hz), 131.1 (d, J = 3.4 Hz), 128.9, 128.5, 128.1, 122.7, 114.4 (d, J = 24.1 Hz). MS (EI, 70 eV): m/z (%) = 342 (100) [M+], 320 (7), 264 (5), 170 (7), 77 (5). HRMS: m/z = 342.122. IR (ATR): 1550 (m), 1473 (s), 1403 (m), 1246 (m), 1183 (m), 1130 (m), 1040 (m), 911 (s), 823 (s), 766 (s), 695 (s) cm1. 3,3′,4,4′-Tetrafluorobiphenyl (2g): mp 83 C; 1H NMR (300 MHz, CDCl3): d = 7.397.32 (m, 2 H), 7.307.25 (m, 4 H). 13C NMR (75 MHz, CDCl3): d = 152.1 (dd, J = 12.7, 23.9 Hz), 148.8 (dd, J = 12.6, 24.8 Hz), 136.2, 123.0 (q, J = 3.4 Hz), 117.8 (d, J = 17.3 Hz), 116.0 (d, J = 17.9 Hz). MS (EI, 70 eV): m/z (%) = 226 (100 [M+], 206 (22), 175 (8), 156 (7), 138 (7), 112 (8). HRMS: m/z = 226.041. IR (ATR): 3064 (w), 1881 (w), 1599 (s), 1495 (s), 1339 (s), 1316 (m), 1265 (s), 1184 (s), 1150 (m), 117 (s), 1028 (m), 943 (m), 909 (m), 885 (m), 865 (s), 805 (s), 766 (s), 739 (s) cm1.
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