Chapter 7. Chan–Lam Coupling Reaction: Copper-promoted C–Element Bond Oxidative Coupling Reaction with Boronic Acids

Chan–Lam coupling is a copper-catalysed N/O-arylation reaction using arylboronic acids. It has emerged as a powerful and useful synthetic methodology for medicinal, crop-protection and material chemists. The Chan–Lam coupling reaction is the only reaction that is capable of forming twelve C-element bonds (N, O, S, P, F, Cl, Br, I, Se, Te, C, H) under mild conditions. It is complementary to and as useful as the Nobel-prize Suzuki–Miyauru C–C bond coupling reaction. This chapter will concentrate on the latest reaction development and industrial applications of Chan–Lam coupling during the period of early 2010 to early 2014, where the usefulness of Chan–Lam coupling has recently been demonstrated in the process chemistry scale-up of a marketed drug. As of early 2014, 73% of the cumulative 840 publications on Chan–Lam coupling reactions are in the patent literature, further attesting to the utility of this important reaction in industry.