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苯并三唑基和亚胺基自由基促进的苯乙烯、吲哚和苯并呋喃的光催化不对称双胺化反应

Photocatalytic Unsymmetrical Diamination of Styrenes, Indoles, and Benzofurans Facilitated by Benzotriazolyl and Iminyl Radicals.

作者信息

Luo Xue-Ling, Ye Dan-Dan, Zheng Judun, Chen Dan-Na, Chen Li-Ning, Li Lin, Li Shu-Hui, Xia Peng-Ju

机构信息

School of Chemistry and Pharmaceutical Sciences, State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Guangxi Normal University, Guilin, Guangxi 541004, P. R. China.

Molecular Diagnosis and Treatment Center for Infectious Diseases, Dermatology Hospital, Southern Medical University, Guangzhou, Guangdong 510091, P. R. China.

出版信息

Org Lett. 2024 Jan 19;26(2):559-564. doi: 10.1021/acs.orglett.3c04148. Epub 2024 Jan 9.

Abstract

Utilizing energy transfer catalysis, this research employed the bifunctional reagents benzotriazole carboxylic acid oxime esters to simultaneously generate benzotriazole and imine radicals. The synthesis of two distinct C-N bonds in a single conversion is showcased through radical addition and radical-radical cross-coupling processes between benzotriazole carboxylic acid oxime ester and olefins. This process facilitates the intermolecular two-component unsymmetrical diamination reaction of olefins. Using this approach, more than 40 benzotriazole-containing molecules were successfully synthesized using styrene, indole, and benzofuran as acceptors, with yields ranging from moderate to excellent.

摘要

本研究利用能量转移催化,采用双功能试剂苯并三唑羧酸肟酯同时生成苯并三唑和亚胺自由基。通过苯并三唑羧酸肟酯与烯烃之间的自由基加成和自由基-自由基交叉偶联过程,展示了在单一转化中合成两种不同C-N键的方法。该过程促进了烯烃的分子间双组分不对称双胺化反应。使用这种方法,以苯乙烯、吲哚和苯并呋喃为受体,成功合成了40多种含苯并三唑的分子,产率从中等到优异。

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