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Benziodoxole Triflate as a Versatile Reagent for Iodo(III)cyclization of Alkynes
Author(s) -
Wu Bin,
Wu Junliang,
Yoshikai Naohiko
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201701530
Subject(s) - trifluoromethanesulfonate , reagent , chemistry , nucleophile , electrophile , aryl , alkyne , trifluoromethyl , combinatorial chemistry , alcohol , organic chemistry , catalysis , alkyl
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‐I III compounds proved easy to purify, stable, and amenable to various synthetic transformations.