Sonogashira Reaction Using Arylsulfonium Salts as Cross-Coupling Partners

Triarylsulfonium, alkyl- and fluoroalkyl­(diaryl)­sulfonium, and aryl­(dialkyl)­sulfonium triflates are successfully used as a new family of cross-coupling participants in the Sonogashira reaction as aryldiazonium, diaryliodonium, and tetraphenylphosphonium salts. It was found that terminal alkynes...

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Bibliographic Details
Published in:Organic letters 2017-10, Vol.19 (19), p.5454-5457
Main Authors: Tian, Ze-Yu, Wang, Shi-Meng, Jia, Su-Jiao, Song, Hai-Xia, Zhang, Cheng-Pan
Format: Article
Language:English
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Summary:Triarylsulfonium, alkyl- and fluoroalkyl­(diaryl)­sulfonium, and aryl­(dialkyl)­sulfonium triflates are successfully used as a new family of cross-coupling participants in the Sonogashira reaction as aryldiazonium, diaryliodonium, and tetraphenylphosphonium salts. It was found that terminal alkynes reacted mildly with triarylsulfonium or (2,2,2-trifluoroethyl)­diphenylsulfonium triflate at room temperature under Pd- and Cu-cocatalysis to give the corresponding arylalkynes in up to >99% yield. This protocol represents the first use of arylsulfonium salts as cross-coupling partners in the Pd/Cu-catalyzed Sonogashira reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02764