HCID 87773595, compound → HCID 178431040, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using N‐(3‐(2‐chlorophenyl)propyl)‐2,2,2‐trifluoroacetamide (66.4 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 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 4:37:55 dimeta:meta:para borylation in 95% 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 1:1.6 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (94.0 mg, 0.24 mmol, 96%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Provenance & Evidence