TY - JOUR
T1 - Benziodoxole Triflate as a Versatile Reagent for Iodo(III)cyclization of Alkynes
AU - Wu, Bin
AU - Wu, Junliang
AU - Yoshikai, Naohiko
N1 - Funding Information:
This work was supported by the Singapore Ministry of Education and Nanyang Technological University (RG3/15, RG114/15, and MOE2016-T2-2–043). We thank Drs. Yongxin Li and Rakesh Ganguly (Nanyang Technological University) for assistance with X-ray crystallographic analysis.
Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/12/14
Y1 - 2017/12/14
N2 - 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.
AB - 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.
KW - alkynes
KW - cross-coupling
KW - cyclization
KW - hypervalent compounds
KW - iodine
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U2 - 10.1002/asia.201701530
DO - 10.1002/asia.201701530
M3 - Article
C2 - 29086497
AN - SCOPUS:85034265249
VL - 12
SP - 3123
EP - 3127
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 24
ER -