Molecules (Jul 2018)

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

  • Yoshihiro Nishimoto,
  • Junyi Yi,
  • Tatsuaki Takata,
  • Akio Baba,
  • Makoto Yasuda

DOI
https://doi.org/10.3390/molecules23081884
Journal volume & issue
Vol. 23, no. 8
p. 1884

Abstract

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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.

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