HCID 178497626, compound → HCID 178497423, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 4g (68.8 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). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 23:1 meta:para borylation in 97% yield (these numbers include a small amount of meta isomer that also underwent NH borylation). The crude product was purified by silica gel chromatography (15% EtOAc in Petroleum Ether 40‐60 o C) which resulted in the cleavage of the N‐B bond in the small amount of N‐borylated product and gave the title compound (as a 17.8:1 mixture of meta:para ratio, as determined by 1 H NMR) as an off‐white solid (97 mg, 0.24 mmol, 97%).

Provenance & Evidence