Palladium-Catalyzed, One-Pot, Three-Component Synthesis of Homoallylic Amines from Aldehydes, Anisidine, and Allyl Trifluoroacetate

Abstract

An allylation reaction that generates homoallylic amines using allyl trifluoroacetate as a nucleophilic allylmetal precursor is reported. A palladium complex catalyzes two transformations in one pot: formation of allylsilane from allyl trifluoroacetate using hexamethyldisilane and subsequent imine allylation. A three-component reaction was developed where preformed imines were replaced with aldehydes and anisidine. Under these reaction conditions a variety of substrates, including electron-rich aromatic and aliphatic aldehydes, react smoothly to afford homoallylic amines.