Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF3SiMe3 and Elemental Sulfur

A metal-free oxidative trifluoromethyl-thiol­ation of terminal alkynes using readily available CF3SiMe3 and elemental sulfur at room temperature has been developed. This reaction provides an efficient and convenient method for the preparation of alkynyl trifluoromethyl sulfides bearing a wide range...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 134; no. 30; pp. 12454 - 12457
Main Authors Chen, Chao, Chu, Lingling, Qing, Feng-Ling
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.08.2012
Amer Chemical Soc
Subjects
air
alkynes
Alkynes - chemistry
ambient temperature
Chemistry
Chemistry, Multidisciplinary
Hydrocarbons, Fluorinated - chemistry
oxidants
Oxidants - chemistry
Oxidation-Reduction
Physical Sciences
Science & Technology
Sulfhydryl Compounds - chemistry
sulfides
sulfur
Sulfur - chemistry
Trimethylsilyl Compounds - chemistry
ALKENES
CROSS-COUPLING REACTIONS
COPPER-CATALYZED TRIFLUOROMETHYLATION
ARYL BORONIC ACIDS
FACILE SYNTHESIS
FLUORINATED ETHERS
SULFIDES
ARENES
REDUCTIVE ELIMINATION
BOND-FORMATION
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ISSN0002-7863
1520-5126
1520-5126
DOI10.1021/ja305801m

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Summary:A metal-free oxidative trifluoromethyl-thiol­ation of terminal alkynes using readily available CF3SiMe3 and elemental sulfur at room temperature has been developed. This reaction provides an efficient and convenient method for the preparation of alkynyl trifluoromethyl sulfides bearing a wide range of functional groups. Preliminary investigation revealed that elemental sulfur instead of air acted as the oxidant.
Bibliography:ObjectType-Article-1
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ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja305801m