Bunte Salts as Thiolating Reagents for Alkenes

Sen Lin describes the synthesis of β-acetamido sulfides using Bunte salts as thiolating reagents.

NaI-Mediated Acetamidosulfenylation of Alkenes with Bunte Salts as Thiolating Reagent Leading to β-Acetamido Sulfides: R. Zhang, Z. Yan, D. Wang, Y. Wang, S. Lin
Synlett 2017, 28, DOI: 10.1055/s-0036-1588144

The β-acetamido sulfide motif is present in a number of biologically active and natural compounds such as lactacystin and others. However, its synthesis is not an easy task to accomplish for the synthetic chemist, especially when it comes to performing the synthesis of β-acetamido sulfides in a user-friendly and efficient manner. Recently, the group of Professor Sen Lin from the Nanchang University (P.R. of China) has reported a novel strategy for readily transforming alkenes into the title compounds using Bunte salts (RS-SO3Na) in very good yields (up to 87%). 

Professor Lin said: 

“In our work, a direct and efficient method for the acetamidosulfenylation reaction of alkenes was developed, in which NaI was used as a catalyst, DMSO as the oxidant, nitriles as both the solvent and nucleophiles and stable, readily available Bunte salts as thiolating reagents. The reactions were carried out under mild conditions generating β-acetamido sulfides in good yields, Moreover, the reaction can be performed when alcohols are used as nucleophiles providing the corresponding β-alkoxysulfides in moderate yields, respectively.”