HCID 178424224, compound → HCID 178423573, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐(o‐tolyl)propyl)acetamide (61.3mg, 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 1.6:1 meta:para borylation in 54% 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 1.5:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (46.0 mg, 0.12 mmol, 50%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Provenance & Evidence