Regio- and Stereoselective Allylindation of Alkynes Using InBr₃ and Allylic Silanes: Synthesis, Characterization, and Application of 1,4-Dienylindiums toward Skipped Dienes

Molecules. 2018 Jul 27;23(8):1884. doi: 10.3390/molecules23081884.

Abstract

Regioselective anti-allylindation of alkynes was achieved using InBr₃ and allylic silanes. Various types of alkynes and allylic silanes were applicable to the present allylindation. This sequential process used the generated 1,4-dienylindiums to establish novel synthetic methods for skipped dienes. The 1,4-dienylindiums were characterized by spectral analysis and treated with I₂ to stereoselectively give 1-iodo-1,4-dienes. The Pd-catalyzed cross coupling of 1,4-dienylindium with iodobenzene successfully proceeded in a one-pot manner to afford the corresponding 1-aryl-1,4-diene.

Keywords: alkyne; allylic silane; allylmetalation; indium.

MeSH terms

  • Alkynes / chemical synthesis
  • Catalysis
  • Indium / chemistry*
  • Molecular Structure
  • Silanes / chemistry*
  • Stereoisomerism

Substances

  • Alkynes
  • Silanes
  • indium bromide
  • Indium