Copper-Catalyzed Regioselective Trifluoromethylthiolation of Pyrroles by Trifluoromethanesulfonyl Hypervalent Iodonium Ylide

The copper-catalyzed trifluoromethylthiolation of pyrroles with a trifluoromethanesulfonyl hypervalent iodonium ylide under mild conditions has been achieved. A broad set of pyrroles could be transformed to the corresponding products in moderate to excellent yields. The reaction mechanism is hypothe...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 5; pp. 1094 - 1097
Main Authors Huang, Zhongyan, Yang, Yu-Dong, Tokunaga, Etsuko, Shibata, Norio
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 06.03.2015
Subjects
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
Physical Sciences
pyrroles
reaction mechanisms
regioselectivity
Science & Technology
BORONIC ACIDS
MILD
MIGRATION
(PERHALOMETHYLTHIO)HETEROCYCLES
SULFIDES
SUBSTITUTIONS
ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION
ARYL
IODINE REAGENT
CHLORIDE
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ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/ol503616y

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Summary:The copper-catalyzed trifluoromethylthiolation of pyrroles with a trifluoromethanesulfonyl hypervalent iodonium ylide under mild conditions has been achieved. A broad set of pyrroles could be transformed to the corresponding products in moderate to excellent yields. The reaction mechanism is hypothesized.
Bibliography:KAKEN
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol503616y