Reacción #1577989

ord-7a7ce259d48648448218c44b7d39ce2e

Ecuación de reacción

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Reactantes

Cc1ccc(-c2ccccc2CCCNC(=O)C(F)(

CAS: 2135636-47-2

Reactivos

C1=CCCC=CCC1.C1=CCCC=CCC1.C[OH

CAS: 12148-71-9

CC1(C)OB(B2OC(C)(C)C(C)(C)O2)O

CAS: 73183-34-3

CCCC[N+](CCCC)(CCCC)CCCC.Cc1cc

CAS: 2007932-96-7

Disolventes

C1CCOC1

CAS: 109-99-9

Condiciones de reacción

Temperatura

50°CELSIUS

Procedimiento

Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐(4'‐methyl‐[1,1'‐biphenyl]‐2‐ yl)propyl)acetamide (80.3 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 10.4:1 meta:para borylation in 99% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐9:1) to give the title compound (as a 9.5:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (102.4 mg, 0.23 mmol, 92%).

Fuente

DOI: 10.1002/anie.201708967Borylation dataset from Roche