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The Reaction of Grignard Reagents with Bunte Salts: A Thiol-Free Synthesis of Sulfides

Jonathan T. Reeves*, Kaddy Camara, Zhengxu S. Han, Yibo Xu, Heewon Lee, Carl A. Busacca and Chris H. Senanayake

*Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States, Email: jonathan.reevesboehringer-ingelheim.com

J. T. Reeves, K. Camara, Z. S. Han, Y. Xu, H. Lee, C. A. Busacca, C. H. Senanayaka, Org. Lett., 2014, 16, 1196-1199.

DOI: 10.1021/ol500067f



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Abstract

S-Alkyl, S-aryl, and S-vinyl thiosulfate sodium salts (Bunte salts), which can readily be prepared from sodium thiosulfate, react with Grignard reagents to give sulfides in good yields. The reaction is amenable to a broad structural array of Bunte salts and Grignard reagents. Importantly, this route to sulfides avoids the use of malodorous thiol starting materials or byproducts.


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Key Words

alkyl sulfides, aryl sulfides, benzyl sulfides, vinyl sulfides, alkynyl sulfides


ID: J54-Y2014