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可见光诱导的乙烯基环丙烷脱羧烷基化/开环及酯化反应

Visible-Light-Induced Decarboxylative Alkylation/Ring Opening and Esterification of Vinylcyclopropanes.

作者信息

Chen Pu, Huang Peng-Fei, Xiong Bi-Quan, Huang Hua-Wen, Tang Ke-Wen, Liu Yu

机构信息

Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan 414006, People's Republic of China.

Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, People's Republic of China.

出版信息

Org Lett. 2022 Aug 12;24(31):5726-5730. doi: 10.1021/acs.orglett.2c02151. Epub 2022 Aug 3.

Abstract

A visible-light-induced four-component reaction of vinylcyclopropanes, -(acyloxy)phthalimide esters, ,-dimethylformamide (DMF), and HO through an oxidative ring opening of cyclopropane is presented. This procedure provides a new and effective way to construct formate esters. DMF is employed as both a solvent and the source of CHO. This difunctionalization of vinylcyclopropanes shows good functional group tolerance under room temperature. A radical pathway is involved, and carbonyl oxygen of ester originated from water in this transformation.

摘要

本文报道了一种可见光诱导的乙烯基环丙烷、(酰氧基)邻苯二甲酰亚胺酯、N,N-二甲基甲酰胺(DMF)和水通过环丙烷氧化开环的四组分反应。该方法为甲酸酯的构建提供了一种新的有效途径。DMF既用作溶剂又作为CHO的来源。乙烯基环丙烷的这种双官能化在室温下表现出良好的官能团耐受性。该反应涉及自由基途径,并且酯的羰基氧在此转化过程中源自水。

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