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Anti-Markovnikov Hydroalkylation of Allylic Amine Derivatives via a Palladium-Catalyzed Reductive Cross-Coupling Reaction

Ryan J. DeLuca and Matthew S. Sigman*

*Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States, Email:

R. J. DeLuca, M. S. Sigman, J. Am. Chem. Soc., 2011, 133, 11454-11457.

DOI: 10.1021/ja204080s (free Supporting Information)

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Palladium-catalyzed reductive cross-coupling reaction of various protected allylic amine derivatives with alkylzinc reagents yields anti-Markovnikov products. 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.

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Key Words

Amines, Benzoquinone

ID: J48-Y2011-2120