HCID 101803207, compound → HCID 178431037, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using N‐(3‐(2‐bromophenyl)propyl)‐2,2,2‐trifluoroacetamide (77.5 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 solventsremoved. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 1:2 meta:para borylation in 93% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐8:1) to give the title compound (as a 1:1.7 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (85.9 mg, 0.20 mmol, 79%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Provenance & Evidence