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Sonogashira Reaction Using Arylsulfonium Salts as Cross-Coupling Partners

Sonogashira Reaction Using Arylsulfonium Salts as Cross-Coupling Partners

Ze-Yu Tian, Shi-Meng Wang, Su-Jiao Jia, Hai-Xia Song, Cheng-Pan Zhang

Org Lett. 2017 Oct 6;19(19):5454-5457.

PMID: 28929767

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP111281120	(4-Phenylthiophenyl)diphenylsulfonium triflate		111281-12-0	Price

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