Olefin Functionalization/Isomerization Enables Stereoselective Alkene Synthesis. Academic Article uri icon


  • Despite tremendous efforts aimed at devising methods for stereoselective alkene synthesis, critical challenges are yet to be addressed. Direct access to a diverse range of 1aryl(boryl)-1-methyl-functionalized tri- and tetrasubstituted trans alkenes, entities that are prevalent in many important molecules of interest, through a catalytic manifold from readily available -olefin substrates remains elusive. Here, we demonstrate that catalytic amounts of a nonprecious N-heterocyclic carbene-Ni(I) complex in conjunction with a sterically bulky base promote site- and trans-selective union of monosubstituted olefins with a wide array of electrophilic reagents to deliver tri- and tetrasubstituted alkenes in up to 92% yield and >98% regio- and stereoselectivity. The protocol is amenable to the preparation of carbon- and heteroatom-substituted C=C bonds, providing distinct advantages over existing transformations. Utility is highlighted through concise stereoselective synthesis of biologically active compounds.

published proceedings

  • Nat Catal

author list (cited authors)

  • Liu, C., Wang, H., Martin, R. T., Zhao, H., Gutierrez, O., & Koh, M. J.

complete list of authors

  • Liu, Chen-Fei||Wang, Hongyu||Martin, Robert T||Zhao, Haonan||Gutierrez, Osvaldo||Koh, Ming Joo

publication date

  • January 2021