Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)



see article for more reactions

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.


see article for more examples



Key Words

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


ID: J54-Y2014