Journal article
Aryl methyl sulfides via SNAr using DMSO as the source of the thiomethyl moiety
Abstract
A unique synthesis of aryl methyl sulfides is reported proceeding via reduction of dimethylsulfoxide to dimethylsulfide at elevated temperature in the presence of Hunig’s base followed by nucleophilic aromatic substitution and demethylation. Activated aryl fluorides, chlorides, and nitrobenzenes are suitable substrates with 13 examples provided. Dimethylsulfoxide serves as a simple and inexpensive formal source of the thiomethyl moiety.
Authors
Jones-Mensah E; Magolan J
Journal
Tetrahedron Letters, Vol. 55, No. 38, pp. 5323–5326
Publisher
Elsevier
Publication Date
September 2014
DOI
10.1016/j.tetlet.2014.07.058
ISSN
0040-4039