HCID 3869638, compound → HCID 178427430, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 4‐methyl‐N‐(2‐(trifluoromethyl)benzyl)benzenesulfonamide (82.3 mg, 0.25 mmol), B2pin2 (95 mg, 0.375 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 solventsremoved. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 2.5:1 meta:para borylation in 88% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1) to give the title compound (as a 17:35:1 mixture of meta:para ratio as determined by 1 H NMR) as a white solid (93 mg), due to the presence of the SM the NMR yield was used for all comparisons. Using a combination of 2D NMR analysis the meta and para isomers are described:

Provenance & Evidence