1. The Reaction of Grignard Reagents with Bunte Salts:A Thiol-Free Synthesis of Sulfides.
- Author
-
Reeves, Jonathan T., Camara, Kaddy, Han, Zhengxu S., Xu, Yibo, Lee, Heewon, Busacca, Carl A., and Senanayake, Chris H.
- Subjects
- *
GRIGNARD reagents , *CHEMICAL reactions , *BUNTE salts , *THIOL synthesis , *SULFIDE synthesis , *THIOSULFATES , *SODIUM salts - Abstract
S-Alkyl,S-aryl, and S-vinyl thiosulfate sodium salts (Bunte salts)react with Grignard reagents to give sulfides in good yields. TheS-alkyl Bunte salts are prepared from odorless sodium thiosulfateby an SN2 reaction with alkyl halides. A Cu-catalyzed couplingof sodium thiosulfate with aryl and vinyl halides was developed toaccess S-aryl and S-vinyl Bunte salts. The reaction is amenable toa broad structural array of Bunte salts and Grignard reagents. Importantly,this route to sulfides avoids the use of malodorous thiol startingmaterials or byproducts. [ABSTRACT FROM AUTHOR]
- Published
- 2014
- Full Text
- View/download PDF