2-Methylbenzylamine, TFA → HCID 178423575, compound

Temperature

50 °C

Following general procedure F using 2,2,2‐trifluoro‐N‐(2‐methylbenzyl)acetamide (54.3 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 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1.1:1 meta:para borylation in 86% yield with 10% SM present. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (17:3) to give the title compound (as a 11:10:1 mixture of meta:para:SM ratio, as determined by 1 H NMR) as a colourless oil (75 mg) with NMR yield used for comparison. By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:

ORD record

ord-eb3dc253a39444108425a28772eae7f5

Source dataset

Borylation dataset from Roche

DOI

10.1002/anie.201708967