jo6b00466_si_001.pdf (5.64 MB)
Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem
journal contribution
posted on 2016-04-05, 00:00 authored by Julien
C. Vantourout, Robert P. Law, Albert Isidro-Llobet, Stephen J. Atkinson, Allan J. B. WatsonThe
Chan–Evans–Lam reaction is a valuable C–N
bond forming process. However, aryl boronic acid pinacol (BPin) ester
reagents can be difficult coupling partners that often deliver low
yields, in particular in reactions with aryl amines. Herein, we report
effective reaction conditions for the Chan–Evans–Lam
amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH
solvent system was found to enable effective C–N bond formation
using aryl amines while EtOH is not required for the coupling of alkyl
amines.