The Reaction of Grignard Reagents with Bunte Salts: A Thiol-Free Synthesis of Sulfides
Organic Letters2014Vol. 16(4), pp. 1196–1199
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Jonathan T. Reeves, Kaddy Camara, Zhengxu S. Han, Yibo Xu, Heewon Lee, Carl A. Busacca, Chris H. Senanayake
Abstract
S-Alkyl, S-aryl, and S-vinyl thiosulfate sodium salts (Bunte salts) react with Grignard reagents to give sulfides in good yields. The S-alkyl Bunte salts are prepared from odorless sodium thiosulfate by an SN2 reaction with alkyl halides. A Cu-catalyzed coupling of sodium thiosulfate with aryl and vinyl halides was developed to access S-aryl and S-vinyl Bunte salts. 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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