Regioselective Copper-catalyzed C-N and C-S Bond Formation using Amines, Thiols and Halobenzoic Acids

Synthesis (Stuttg). 2007 Nov 16:(22):3519-3527. doi: 10.1055/s-2007-990875.

Abstract

A regioselective method for highly efficient C-N and C-S bond formation with 2-halobenzoic acids is described. The Cu/Cu(2)O-catalyzed reaction is carried out in 2-ethoxyethanol or ethylene glycol diethyl ether and does not require the use of strong base or other additives. This procedure eliminates the need for acid protection, tolerates a wide range of functional groups and provides aromatic and aliphatic amines and sulfides in 81 to 99% yield.