Copper‐Catalyzed Multicomponent Coupling of Organoindium Reagents with Nitrogen‐Containing Aromatic Heterocycles

A mild, copper‐catalyzed coupling of organoindium reagents with nitrogen‐containing aromatic heterocycles and chloroformates is described. This reaction proceeds with a range of organoindium reagents, yielding predominately or exclusively the 1,4‐addition products with pyridine. In addition, a range of other nitrogen‐containing heterocycles can be employed in this reaction (e.g. benzoxazole, benzothiazole, phthalazine). As an illustration of the utility of this reaction, this heterocycle functionalization is coupled with a subsequent oxidation to achieve the one‐pot synthesis of functionalized pyridine and benzothiazole derivatives.