HCID 178521919, compound → HCID 178431034, compound

Temperature

50 °C

Following general procedure F using cis‐12a (67.8 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 3.4:0.4:1 meta:dimeta:para borylation (overall meta:para ratio of 3.8:1) in 64% yield (with 36% unreacted starting material). The crude product was purified by silica gel chromatography (10% EtOAc in Petroleum Ether 40‐60 o C) and the monoborylated products were partially separated from the dimeta product. Mono borylated products were isolated as colourless oil (52 mg) with 3.7:1 meta:para ratio (as determined by 1 H NMR). A small amount of B2Pin2 impurity was found to be inseparable from the final product on silica. Corrected yield ‐ 50 mg, 0.13 mmol, 52%.

ORD record

ord-4c7acd93e4124831a14ceebdcdf6b869

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967