Organic Chemistry Portal



Fast and Highly Chemoselective Alkynylation of Thiols with Hypervalent Iodine Reagents Enabled through a Low Energy Barrier Concerted Mechanism

Reto Frei, Matthew D. Wodrich, Durga Prasad Hari, Pierre-Antoine Borin, Clément Chauvier and Jérôme Waser*

*Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland, Email:

R. Frei, M. D. Wodrich, D. P. Hari, P.-A. Borin, C. Chauvier, J. Waser, J. Am. Chem. Soc., 2014, 136, 16563-16573.

DOI: 10.1021/ja5083014


Alkynylation of thiols using ethynyl benziodoxolone (EBX) hypervalent iodine reagents enables the synthesis of aryl- and alkyl-substituted alkynes containing a broad range of functional groups. New sulfur nucleophiles such as thioglycosides, thioacids, and sodium hydrogen sulfide were also alkynylated successfully to lead to a general and practical method for the synthesis of thioalkynes.

see article for more examples

Tosyloxybenziodoxolone: A Platform for Performing the Umpolung of Alkynes in One-Pot Transformations

J. Borrel, J. Waser, Org. Lett., 2022, 24, 142-146.

Key Words

alkynyl sulfides

ID: J48-Y2014