HCID 78990988, compound → HCID 178423574, compound

Temperature

70 °C

Following general procedure F using 4i (58 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 70 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed ~7:1 meta:para borylation in 69% yield (30% starting material remaining). The crude product was purified by silica gel chromatography (20% EtOAc in Petroleum Ether 40‐60 o C), however this gave a mixture of the borylated products and starting material, which were inseparable on silica (8.2:1:2.3 mixture of meta:para:starting material ratio, as determined by 1 H NMR), as a colourless oil (60 mg). As the mixture contained 20% of starting material, the isolated yield was corrected by calculating the mass of the starting material in the mixture. Corrected yield for the borylated products was 52 mg, 0.15 mmol, 58%.

ORD record

ord-f0a2a27e40604dfc87dd0d8376f6be53

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967