Heteroatom Chemistry (Jan 2019)

One-Pot Synthesis of Hypervalent Diaryl(iodo)bismuthanes from o-Carbonyl Iodoarenes by Zincation

  • Toshihiro Murafuji,
  • A. F. M. Hafizur Rahman,
  • Daiki Magarifuchi,
  • Masahiro Narita,
  • Isamu Miyakawa,
  • Katsuya Ishiguro,
  • Shin Kamijo

DOI
https://doi.org/10.1155/2019/2385064
Journal volume & issue
Vol. 2019

Abstract

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Diaryl(iodo)bismuthanes possessing a hypervalent C=O•••Bi–I bond were conveniently synthesized in a one-pot reaction by using arylzinc reagents generated from o-carbonyl iodobenzenes and zinc powder under ultrasonication. This method is superior to the conventional organolithium and Grignard methods because it has a wide functional group tolerance, requires no protecting group manipulations, and proceeds under mild reaction conditions that do not need low temperature control. Furthermore, no intermediate triarylbismuthane precursor for the hypervalent iodobismuthane is necessary.