BF·OEt 介导的亚磺酸钠的不均衡偶联反应：一种合成对称/不对称硫代磺酸盐的方法。
Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF·OEt: An Approach to Symmetrical/Unsymmetrical Thiosulfonates.
机构信息
School of Chemistry and Environment , South China Normal University, Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education , Guangzhou 510006 , P. R. China.
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering , South China University of Technology , 381 Wushan Road , Guangzhou 510640 , P. R. China.
出版信息
Org Lett. 2018 Aug 17;20(16):4754-4758. doi: 10.1021/acs.orglett.8b01808. Epub 2018 Aug 1.
The BF·OEt-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O) bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation. What is more, this transformation can also be applied practically as a gram-scale reaction and to the two-step synthesis of sulfone and sulfonamide in one pot in situ using thiosulfonate as an intermediate.
BF·OEt 介导的亚磺酸钠的不均衡偶联反应为首次发现。在此反应中，多种 S-S(O) 键可形成，以中等至优秀的收率高效地得到硫代硫酸盐。作为一种合成对称和不对称硫代硫酸盐的方便方法，其反应机理涉及通过亚磺酰基自由基歧化形成硫自由基和磺酰基自由基。更重要的是，这种转化还可以实际应用于克级规模的反应，并且可以使用硫代硫酸盐作为中间体一锅法进行两步合成砜和磺酰胺。
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