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.reeves
boehringer-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
