HCID 17949209, compound → HCID 178474519, compound

Temperature

50 °C

Following general procedure F using N‐(2‐(trifluoromethyl)benzyl)acetamide (54.3 mg, 0.25 mmol), B2pin2 (95 mg, 0.375 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and dtbpy (2.0 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 1:1.1 meta:para borylation in 92% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (7:3) to give the title compound (as a 1:1.9 mixture of meta:para ratio with pinacol and B2pin2 as determined by 1 H NMR) as a white solid (59.7 mg), due to multiple impurities, the NMR yield was used for all comparisons. By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

ORD record

ord-8010aff80abc4b47811060147030b55e

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967