HCID 62491089, compound → HCID 178431092, compound

Participants

Reaction Conditions

Reaction Steps

Following general procedure F using 4m (54.5 mg, 0.25 mmol), B2pin2 (95.2 mg, 0.375 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and dtbpy (2.0 mg, 0.0075 mmol) in THF (1.25 mL). Stirred in vial at 35 °C for 6 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 2:1:0.4 meta:para:di(3,5) borylation (overall meta:para borylation 1.4:1) in 99% yield. Purification by silica gel chromatography proved not to be possible, leading to product decomposition. As such, the compounds was characterised from the crude, which contained pinacol borane impurity. By subtracting the resonances for the meta isomer, the NMR data of the para and di(3,5) borylated isomer can be assigned as follows:

Provenance & Evidence