2,2,2-trifluoro-N-[[2-(trifluoromethyl)phenyl]methyl]acetamide → 2,2,2-trifluoro-N-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenyl]methyl]acetamide

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Reaction Conditions

Reaction Steps

Following general procedure F using 2,2,2‐trifluoro‐N‐(2‐(trifluoromethyl)benzyl)acetamide (67.8 mg, 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 rt for 20 hours before cooling and the solventsremoved. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 1:1 meta:para borylation in 99% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1‐7:1) to give the title compound (as a 1:1.1:0.7 mixture of meta:para:B2pin2 ratio, as determined by 1 H NMR) as a colourless oil (50.1 mg, 0.13 mmol, 50%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

Provenance & Evidence