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

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, af...

Full description

Saved in:
Bibliographic Details
Published inChemistry, an Asian journal Vol. 12; no. 24; pp. 3123 - 3127
Main Authors Wu, Bin, Wu, Junliang, Yoshikai, Naohiko
Format Journal Article
LanguageEnglish
Published Germany Wiley Subscription Services, Inc 14.12.2017
Subjects
Alkynes
Aromatic compounds
Chemistry
cross-coupling
cyclization
hypervalent compounds
Indoles
iodine
cross-coupling
iodine
cyclization
hypervalent compounds
alkynes
Online AccessGet full text

Cover

More Information
Summary: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. Hyperactive: A benziodoxole triflate promotes iodo(III)cyclization of alkynes tethered to a variety of nucleophilic moieties, affording benziodoxole‐appended (hetero)arenes such as benzofurans, benzothiophenes, isocoumarins, indoles, and polyaromatics. These unprecedented (hetero)aryl‐IIII compounds are easy to purify, air‐ and thermally stable, and amenable to various synthetic transformations.
Bibliography:Both authors contributed equally to this work.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1861-4728
1861-471X
DOI:10.1002/asia.201701530