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)
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.
see article for more examples
M.-Y. Ngai, A. Barchuk, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 12644-12645.
E. Skucas, J. R. Kong, M. J. Krische, J. Am. Chem. Soc., 2007, 129, 7242-7243.