title: The reaction of Grignard reagents with Bunte salts: a thiol-free synthesis of sulfides.
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.
authors: Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc. , 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
authors: Jonathan T
authors: JT
authors: Reeves
authors: Kaddy
authors: K
authors: Camara
authors: Zhengxu S
authors: ZS
authors: Han
authors: Yibo
authors: Y
authors: Xu
authors: Heewon
authors: H
authors: Lee
authors: Carl A
authors: CA
authors: Busacca
authors: Chris H
authors: CH
authors: Senanayake
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007202:Indicators and Reagents; D013440:Sulfides; D003300:Copper