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Allylic Amines via Iridium-Catalyzed C-C Bond Forming Hydrogenation: Imine Vinylation in the Absence of Stoichiometric Byproducts or Metallic Reagents

Andriy Barchuk, Ming-Yu Ngai and Michael J. Krische*

*Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, Email: mkrischemail.utexas.edu

A. Barchuk, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 8432-8433.

DOI: 10.1021/ja073018j (free Supporting Information)


Abstract

Exposure of various N-arylsulfonyl aldimines to 2-butyne and hydrogen at ambient pressure in the presence of a cationic iridium(I) catalyst modified by BIPHEP provides reductive coupling products, allylic amines, in good yields as single geometrical isomers. Nonsymmetric alkynes couple under standard conditions with high levels of regioselection.

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Enantioselective Iridium-Catalyzed Imine Vinylation: Optically Enriched Allylic Amines via Alkyne−Imine Reductive Coupling Mediated by Hydrogen

M.-Y. Ngai, A. Barchuk, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 12644-12645.

Enantioselective Reductive Coupling of Acetylene to N-Arylsulfonyl Imines via Rhodium Catalyzed C-C Bond-Forming Hydrogenation: (Z)-Dienyl Allylic Amines

E. Skucas, J. R. Kong, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 7242-7243.


Key Words

Allylic Amines, Hydrogen, Multicomponent Reactions


ID: J48-Y2007-2180