HCID 178497625, compound → HCID 178497422, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using using methyl 2‐(3‐(2,2,2‐trifluoroacetamido)propyl)benzoate (57.9 mg, 0.20 mmol), B2pin2 (101 mg, 0.40 mmol), [Ir(COD)OMe]2 (2.0 mg, 0.0030 mmol) and dtbpy (1.6 mg, 0.0060 mmol) in THF (1.0 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 3:1 meta:para borylation in 76% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1‐8:1) to give the title compound (as a 2.7:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (43.0 mg, 0.10 mmol, 69%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Provenance & Evidence