Abstract

The Chan–Lam reaction is a copper-mediated or -catalyzed formation of a wide variety of carbon–heteroatom bonds from an organoboron compound and a heteroatom nucleophile. In its broadest sense, The Reaction">the reaction allows arylation, vinylation, and alkylation of a wide range of heteroatom-based functional groups including amines, amides, sulfonamides, N-heterocycles, alcohols, phenols, and thiols. The coupling partner is usually a boronic acid, although boronic esters have also been successful. An inexpensive copper mediator or catalyst, such as copper(II) acetate, is employed in the reaction. The typically mild, user-friendly reaction conditions often involve an atmosphere of air, ambient temperature, and no ligand.

This chapter presents a thorough overview of the Chan–Lam reaction with N-, O-, and S-based nucleophiles. The current understanding of the reaction mechanism is discussed along with a detailed overview of the scope and limitations of the process, and representative reaction conditions. Applications in the context of complex molecule synthesis are provided, as are comparisons to complementary metal-catalyzed heteroatom-functionalization methods using copper and palladium.