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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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
Online AccessGet full text
ISSN1523-7060
1523-7052
1523-7052
DOI10.1021/ol503616y

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Abstract 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.
AbstractList 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.
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.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.
Author Shibata, Norio
Yang, Yu-Dong
Huang, Zhongyan
Tokunaga, Etsuko
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  surname: Yang
  fullname: Yang, Yu-Dong
  organization: Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya466-8555, Japan
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  givenname: Etsuko
  surname: Tokunaga
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  givenname: Norio
  surname: Shibata
  fullname: Shibata, Norio
  organization: Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya466-8555, Japan
BackLink https://www.ncbi.nlm.nih.gov/pubmed/25685938$$D View this record in MEDLINE/PubMed
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Issue 5
Keywords BORONIC ACIDS
MILD
MIGRATION
(PERHALOMETHYLTHIO)HETEROCYCLES
SULFIDES
SUBSTITUTIONS
ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION
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Publisher Amer Chemical Soc
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Snippet The copper-catalyzed trifluoromethylthiolation of pyrroles with a trifluoromethanesulfonyl hypervalent iodonium ylide under mild conditions has been achieved....
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StartPage 1094
SubjectTerms chemical reactions
chemical structure
Chemistry
Chemistry, Organic
Physical Sciences
pyrroles
reaction mechanisms
regioselectivity
Science & Technology
Title Copper-Catalyzed Regioselective Trifluoromethylthiolation of Pyrroles by Trifluoromethanesulfonyl Hypervalent Iodonium Ylide
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https://www.ncbi.nlm.nih.gov/pubmed/25685938
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Volume 17
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