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Synthesis of β,β-Dithioketones by Merging C–C and C–S Bond Cleavage in [1 + 1 + 1 + 1 + 1 + 1] Annulation
Organic Letters ( IF 5.2 ) Pub Date : 2024-05-14 , DOI: 10.1021/acs.orglett.4c01364
Dong-Sheng Yang 1 , Xiang-Long Chen 1 , Chun-Yan Wu 1 , Bo-Cheng Tang 2 , Yong-Cheng Xiao 1 , Yan-Dong Wu 1 , An-Xin Wu 1, 3
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An unconventional [1 + 1 + 1 + 1 + 1 + 1] annulation process was developed for the construction of β,β-dithioketones by merging C–C and C–S bond cleavage. In this reaction, rongalite concurrently served as triple C1 units, dual sulfur(II) synthons, and a reductant for the first time. Mechanism investigation indicated that the reaction involved the self-mediated valence state change of rongalite. By performing this step-economical method, the challenging construction of C5-substituted 1,3-dithiane can be achieved under mild and simple conditions.

中文翻译:


通过合并 [1 + 1 + 1 + 1 + 1 + 1] 环化中的 C–C 和 C–S 键断裂合成 β,β-二硫酮



开发了一种非常规的[1 + 1 + 1 + 1 + 1 + 1]成环工艺,通过合并C-C和C-S键断裂来构建β,β-二硫酮。在此反应中,雕白粉首次同时充当三C1单元、双硫(II)合成子和还原剂。机理研究表明该反应涉及雕白粉自介导的价态变化。通过这种经济的步骤,可以在温和且简单的条件下实现具有挑战性的C 5 -取代的1,3-二噻烷的构建。
更新日期:2024-05-14
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