Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water.

Author(s) Lin, Y.M.; Lu, G.P.; Wang, G.X.; Bin Yi, W.
Journal J Org Chem
Date Published 2017 Jan 06
Abstract

A newly developed aqueous system with acid and phosphide was introduced in which odorless and stable sodium arylsulfinates can in situ generate arylsulfenyl radicals. These radicals have high reactivity to react with alkynes, alkenes, and H-phosphine oxides for the synthesis of alkyl and alkenyl sulfides and phosphonothioates. The control experiments and quantum calculations are also performed to gain insights into the generation mechanism of arylsulfenyl radicals. Notably, the chemistry is free of thiol odors, organic solvents, and metals.

DOI 10.1021/acs.joc.6b02459
ISSN 1520-6904
Citation Lin Y-, Lu G-, Wang G-, Bin Yi W-. Acid/Phosphide-Induced Radical Route to Alkyl and Alkenyl Sulfides and Phosphonothioates from Sodium Arylsulfinates in Water. J Org Chem. 2017;82(1):382-389.

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