Benziodoxole Triflate as a Versatile Reagent for Iodo(III)cyclization of Alkynes

Bin Wu, Junliang Wu, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

Abstract

The utility of benziodoxole triflate, derived from α,α-bis(trifluoromethyl)-2-iodobenzyl alcohol, as a versatile reagent for iodo(III)cyclization via electrophilic activation of alkyne, is reported herein. The reagent promotes cyclization of alkynes tethered to a variety of nucleophilic moieties, affording benziodoxole-appended (hetero)arenes such as benzofurans, benzothiophenes, isocoumarins, indoles, and polyaromatics under mild conditions. This unprecedented class of (hetero)aryl-IIII compounds proved easy to purify, stable, and amenable to various synthetic transformations.

Original languageEnglish
Pages (from-to)3123-3127
Number of pages5
JournalChemistry - An Asian Journal
Volume12
Issue number24
DOIs
Publication statusPublished - 2017 Dec 14
Externally publishedYes

Keywords

  • alkynes
  • cross-coupling
  • cyclization
  • hypervalent compounds
  • iodine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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