HCID 178523284, compound → HCID 178431086, compound

Temperature

35 °C

Following general procedure F using N‐(3‐(3‐fluorophenyl)propyl)‐2,2,2‐trifluoroacetamide (62.3 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 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 35 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1.4:1 meta:para borylation in 92% 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 1.3:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (51.4 mg, 0.14 mmol, 55%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

ORD record

ord-ecd9643eeec54ad3ad0e7b4f571b441a

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967