"One-pot" two-step synthesis of aryl sulfur compounds by photoinduced reactions of thiourea anion with aryl halides

Org Lett. 2003 Oct 30;5(22):4133-6. doi: 10.1021/ol035545n.

Abstract

[reaction: see text]. The photoinduced reactions of aryl halides with the thiourea anion afford arene thiolate ions in DMSO. These species without isolation, and by a subsequent aliphatic nucleophilic substitution, S(RN)1 reaction, oxidation, or protonation, yield aryl methyl sulfides, diaryl sulfides, diaryl disulfides, and aryl thiols with good yields (50-80%). This is a simple and convenient approach which involves the use of the commercially available and inexpensive thiourea in a "one-pot" two-step process for the synthesis of aromatic sulfur compounds.