title: Anti-Markovnikov hydroalkylation of allylic amine derivatives via a palladium-catalyzed reductive cross-coupling reaction.
abstract: Palladium-catalyzed hydroalkylation of allylic amine derivatives by alkylzinc reagents is reported. This reductive cross-coupling reaction yields anti-Markovnikov products using a variety of allylic amine protecting groups. Preliminary mechanistic studies suggest that a reversible β-hydride elimination/hydride insertion process furnishes the primary Pd-alkyl intermediate, which then undergoes transmetalation followed by reductive elimination to form a new sp(3)-sp(3) carbon-carbon bond.
authors: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
authors: Ryan J
authors: RJ
authors: DeLuca
authors: Matthew S
authors: MS
authors: Sigman
mesh_terms: D000478:Alkylation; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000588:Amines; D010165:Palladium