Sulfoxidation of alkenes and alkynes with NFSI as a radical initiator and selective oxidant

Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol-ene...

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Published inChemical communications (Cambridge, England) Vol. 53; no. 1; pp. 184 - 187
Main Authors Zhang, Yuexia, Wong, Zeng Rong, Wu, Xingxing, Lauw, Sherman J. L., Huang, Xuan, Webster, Richard D., Chi, Yonggui Robin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2017
Subjects
Alkenes
Alkynes
Chemistry
Chemistry, Multidisciplinary
Initiators
Oxidants
Oxidizing agents
Physical Sciences
Radicals
Science & Technology
Sulfides
Thiols
CHEMOSELECTIVE OXIDATION
COMPLEX
PUMMERER REACTION
ALPHA-FLUORINATION
SULFIDES
AMINOFLUORINATION
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Summary:Sulfoxides are important functional molecules. We develop a short-route (one-pot) synthesis of this class of molecules by reacting thiols with alkenes or alkynes under mild and metal-free conditions. N-Fluorobenzenesulfonimide (NFSI) is used to play dual roles: as a radical initiator for a thiol-ene/-yne reaction to form sulfide adducts, and as efficient oxidant for conversion of the sulfides formed in situ to sulfoxides. Over-oxidation of the sulfoxides to sulfones is avoided in our approach.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc08631d