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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: jerome.waserepfl.ch

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 (free Supporting Information)


Abstract

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.


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Key Words

alkynyl sulfides


ID: J48-Y2014