磺酰亚胺基氟化物的无硅SuFEx反应：范围、对映选择性及机理

Liang Dong-Dong, Streefkerk Dieuwertje E, Jordaan Daan, Wagemakers Jorden, Baggerman Jacob, Zuilhof Han

Laboratory of Organic Chemistry, Wageningen University, Stippeneng 4, 6708WE, Wageningen, The Netherlands.

School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Tianjin, China.

Angew Chem Int Ed Engl. 2020 May 4;59(19):7494-7500. doi: 10.1002/anie.201915519. Epub 2020 Mar 11.

SuFEx reactions, in which an S-F moiety reacts with a silyl-protected phenol, have been developed as powerful click reactions. In the current paper we open up the potential of SuFEx reactions as enantioselective reactions, analyze the role of Si and outline the mechanism of this reaction. As a result, fast, high-yielding, "Si-free" and enantiospecific SuFEx reactions of sulfonimidoyl fluorides have been developed, and their mechanism shown, by both experimental and theoretical methods, to yield chiral products.

已开发出硫氟交换（SuFEx）反应，其中S-F部分与硅烷基保护的苯酚发生反应，该反应已成为强大的点击反应。在本文中，我们开拓了SuFEx反应作为对映选择性反应的潜力，分析了硅的作用并概述了该反应的机理。结果，开发出了磺酰亚胺基氟化物的快速、高产率、“无硅”且对映体特异性的SuFEx反应，并通过实验和理论方法表明其机理可产生手性产物。