Stereocontrolled Synthesis of Halovinylbenziodoxoles by Hydro- and Iodochlorination of Ethynylbenziodoxoles

Junliang Wu, Xiaozhou Deng, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

Abstract

We report herein the synthesis of highly substituted and stereochemically well-defined vinylbenziodoxole (VBX) derivatives through hydrochlorination and iodochlorination of ethynylbenziodoxoles. The hydrochlorination is achieved using pyridine hydrochloride as an HCl source in an anti-fashion under mild, open-air conditions to afford a 2-chlorinated VBX product, which serves as a useful building block for the stereoselective synthesis of trisubstituted alkenes. Meanwhile, iodochlorination with iodine monochloride proceeds in an unusual syn-pathway, stereoselectively affording a tetrasubstituted VBX derivative.

Original languageEnglish
Pages (from-to)7839-7842
Number of pages4
JournalChemistry - A European Journal
Volume25
Issue number33
DOIs
Publication statusPublished - 2019 Jun 12
Externally publishedYes

Keywords

  • alkynes
  • cross-coupling
  • dihalogenation
  • hydrohalogenation
  • hypervalent iodine compounds

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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