Palladium-catalyzed, one-pot, three-component synthesis of homoallylic amines from aldehydes, anisidine, and allyl trifluoroacetate.
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.
Grote
Robin E
RE
Natural Sciences I 4114, Department of Chemistry, University of California, Irvine, Irvine California 92697, USA.
Jarvo
Elizabeth R
ER