HCID 178423712, compound → HCID 178423658, compound

Participants

Reaction Conditions

Reaction Steps

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 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 meta:para borylation in 100% 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 1:1.1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (95.0 mg, 0.21 mmol, 85%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Provenance & Evidence