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Updated: Feb 19, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Benziodoxole Triflate as a Versatile Reagent for Iodo(III)cyclization of Alkynes
Bin Wu1, Junliang Wu1, Naohiko Yoshikai1
1Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
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.
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