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用于合成稠合偕二氟氧杂环丁烷的环丙醇与α-三氟甲基取代烯烃的光催化串联反应

Photocatalyzed Cascade Reactions of Cyclopropanols and α-Trifluoromethyl-Substituted Olefins for the Synthesis of Fused gem-Difluorooxetanes.

作者信息

Zhang Yunxiao, Niu Yunhong, Guo Youyuan, Wang Jiaxin, Zhang Yizhi, Liu Shanshan, Shen Xiao

机构信息

Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072, China.

出版信息

Angew Chem Int Ed Engl. 2022 Nov 2;61(44):e202212201. doi: 10.1002/anie.202212201. Epub 2022 Oct 5.

Abstract

Fluorinated fused rings are challenging to construct from simple starting materials. Herein, we report the first photocatalyzed cascade reactions of readily available cyclopropanols and α-trifluoromethyl-substituted olefins for the synthesis of fused gem-difluorooxetanes. Two rings and three bonds were efficiently constructed in one reaction. The reaction showed broad substrate scope and the downstream transformations of the products demonstrated the synthetic potential of the reaction. The mechanistic study supported the presence of cascade photoredox catalysis and energy transfer catalysis/direct photo-excitation processes.

摘要

从简单的起始原料构建氟化稠环具有挑战性。在此,我们报道了首例光催化的易得环丙醇与α-三氟甲基取代烯烃的串联反应,用于合成稠合偕二氟氧杂环丁烷。在一个反应中高效构建了两个环和三个键。该反应底物范围广泛,产物的下游转化展示了该反应的合成潜力。机理研究支持了串联光氧化还原催化以及能量转移催化/直接光激发过程的存在。

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