Photocatalyzed Cascade Reactions of Cyclopropanols and α-Trifluoromethyl-Substituted Olefins for the Synthesis of Fused gem-Difluorooxetanes
Dr. Yunxiao Zhang
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
These authors contributed equally to this work.
Search for more papers by this authorYunhong Niu
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
These authors contributed equally to this work.
Search for more papers by this authorYouyuan Guo
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorJiaxin Wang
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorYizhi Zhang
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorDr. Shanshan Liu
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiao Shen
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorDr. Yunxiao Zhang
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
These authors contributed equally to this work.
Search for more papers by this authorYunhong Niu
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
These authors contributed equally to this work.
Search for more papers by this authorYouyuan Guo
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorJiaxin Wang
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorYizhi Zhang
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorDr. Shanshan Liu
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Xiao Shen
Institute for Advanced Studies, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University, 299 Bayi Road, Wuhan, Hubei 430072 China
Search for more papers by this authorGraphical Abstract
A combination of photoredox catalysis and energy transfer catalysis/direct photo-excitation enables cascade reactions of cyclopropanols and α-CF3-olefins, in which two rings and three bonds are constructed in one reaction, affording fused gem-difluorooxetanes. The reaction shows broad substrate scope, complete cis-selectivity, and downstream transformations of the products demonstrated the synthetic potential.
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.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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