NaSH-HCl mediated reduction of sulfoxides into sulfides under organic solvent-free reaction conditions. Issue 4 (1st October 2020)

• Record Type: Journal Article
• Authors: Zupanc, Anže; Jereb, Marjan
• Is Part Of: Green chemistry letters and reviews. Volume 13:Issue 4(2020)
• Page Start: 341
• Page End: 348
• Publication Date: 2020-10-01
• Subjects: Sulfoxides -- reduction -- sulfides -- solvent-free; Green chemistry -- Periodicals; 540
• DOI: 10.1080/17518253.2020.1838625
• Languages: English
• ISSNs: 1751-8253

Abstract

ABSTRACT: NaSH·H2 O and 37% aqueous solution of HCl were employed in reduction of sulfoxides to sulfides at room or elevated temperature in the absence of organic reducing agent and solvent-free reaction conditions. Operationally simple transformation took place in the presence of air and in the absence of heavy metals and organic reagents, yielding sodium chloride and sulfur as non-hazardous waste. Heterogeneous reaction conditions proved challenging, particularly in the cases of more hydrophobic substrates, requiring elevated amount of reactants and temperature. Products were isolated by extraction with tert -butyl methyl ether and "filtered" over a short pad of silica gel. Scale-up reaction was demonstrated, including completely solvent-free isolation and purification of the product. A potential reaction course was proposed. GRAPHICAL ABSTRACT: UF0001