Synthesis of Sulfones and Sulfonamides via Sulfinate Anions: Revisiting the Utility of Thiosulfonates
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- 作者：Pranab K. Shyam ; Hye-Young Jang
- 刊名：Journal of Organic Chemistry
- 出版年：2017
- 出版时间：February 3, 2017
- 年：2017
- 卷：82
- 期：3
- 页码：1761-1767
- 全文大小：482K
- ISSN：1520-6904
文摘
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 SO2, thiosulfinates are proposed to be stable, nontoxic alternatives to metal sulfinate salts.