General approach to the coupling of organoindium reagents with imines via copper catalysis.
[reaction: see text] A copper-catalyzed three-component coupling of organoindium reagents with imines and acid chlorides is described. This mild carbon-carbon bond forming reaction requires only one-third of an equivalent of indium reagent to proceed in high yield, with the sole byproduct being indium trichloride. The reaction demonstrates broad generality, with aryl-, heteroaryl-, vinyl-, and alkylindiums, as well as functionalized imines and acid chlorides, all providing alpha-substituted amides or N-protected amines in a single step.
Black
Daniel A
DA
Department of Chemistry, McGill University, Montreal, Quebec, Canada.
Arndtsen
Bruce A
BA