HCID 178463897, compound → HCID 178463895, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using N‐(3‐(2‐Bromophenyl)propyl)‐N‐ethyl‐2,2,2‐trifluoroacetamide (169 mg, 0.50 mmol), B2pin2 (190 mg, 0.75 mmol), [Ir(COD)OMe]2 (5.0 mg, 0.0075 mmol) and 5,5’‐ dimethyl‐2,2’‐dipyridyl (2.8 mg, 0.015 mmol) in THF (2.5 mL). The reaction was stirred at 40 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐ dimethoxyethane showed 1:1.4 meta:para borylation in 98% 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 colourless oil (191 mg, 0.37 mmol, 74%*) as a 1:1.6 meta:para mixture containing 17% B2pin2. *Adjusted yield accounting for B2pin2

Provenance & Evidence