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J Org Chem. 2017 Feb 03;82(3):1761-1767. doi: 10.1021/acs.joc.6b03016. Epub 2017 Jan 25.

Synthesis of Sulfones and Sulfonamides via Sulfinate Anions: Revisiting the Utility of Thiosulfonates.

The Journal of organic chemistry

Pranab K Shyam, Hye-Young Jang

Affiliations

  1. Department of Energy Systems Research, Ajou University , Suwon 16499, Korea.

PMID: 28078894 DOI: 10.1021/acs.joc.6b03016

Abstract

Simple and high-yielding strategies for the production of a variety of sulfones and sulfonamides, using thiosulfonates synthesized by copper-catalyzed aerobic dimerization, are reported. Although thiosulfonates are an old class of compound, practical methods for their synthesis and utilization have not been rigorously developed. In this study, we revisit the reactions of easily accessible thiosulfonates to form sulfinate anions. Because of the similar reactivity of thiosulfonates and metal sulfinates derived from toxic SO

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