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.waser
epfl.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
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.
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
ID: J48-Y2014
