The Chan–Lam Reaction

<jats:title>Abstract</jats:title> <jats:p> 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 allows arylation, vinylation, and alkylation of a wide range of heteroatom‐based functional groups including amines, amides, sulfonamides, <jats:italic>N</jats:italic> ‐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. </jats:p> <jats:p> This chapter presents a thorough overview of the Chan–Lam reaction with <jats:italic>N</jats:italic> ‐, <jats:italic>O</jats:italic> ‐, and <jats:italic>S</jats:italic> ‐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. </jats:p>