Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Copper-Catalyzed Trifluoromethylthiolation of Enamines, Indoles, and β‑Keto Esters

A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluorom...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 135; no. 24; pp. 8782 - 8785
Main Authors Yang, Yu-Dong, Azuma, Ayaka, Tokunaga, Etsuko, Yamasaki, Mikio, Shiro, Motoo, Shibata, Norio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.06.2013
Amer Chemical Soc
Subjects
Amines - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
chlorides
copper
Copper - chemistry
esters
Esters - chemistry
Hydrocarbons, Fluorinated - chemistry
indoles
Indoles - chemistry
Ketones - chemistry
Onium Compounds - chemistry
Oxidation-Reduction
Physical Sciences
Science & Technology
Sulfhydryl Compounds - chemistry
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ISSN0002-7863
1520-5126
1520-5126
DOI10.1021/ja402455f

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Summary:A novel electrophilic-type trifluoromethylthiolation reagent, a trifluoromethanesulfonyl hypervalent iodonium ylide, was designed and reacted well with various nucleophiles to afford the desired CF3S-substituted products. In situ reduction of the trifluoromethanesulfonyl group to give the trifluoromethylthio group, which is the key step in this process, was realized in the presence of copper(I) chloride.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja402455f