2-Methylbenzylamine, TFA → HCID 178423575, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 2,2,2‐trifluoro‐N‐(2‐methylbenzyl)acetamide (54.3 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 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 7.8:1 meta:para borylation in 93% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (17:3)* to give the title compound (as a 7.7:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (77 mg, 0.20 mmol, 90%).

Provenance & Evidence