Selective C–F Bond Etherification of Trifluoromethylalkenes with Phenols

Selective functionalization of a single sp3 C–F bond of the CF3 group represents an appealing way to generate the pharmaceutically privileged difluoromethylene moiety. Herein, a novel protocol for the C–F bond etherification of trifluoromethylalkenes and phenols is reported. A variety of alkenyl dif...

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Published in:Journal of organic chemistry 2022-08, Vol.87 (16), p.10908-10916
Main Authors: Tian, Qingqiang, Pei, Boqun, Wang, Chuxia, Zhang, Chiying, Li, Yahui
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Language:English
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creator Tian, Qingqiang
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description Selective functionalization of a single sp3 C–F bond of the CF3 group represents an appealing way to generate the pharmaceutically privileged difluoromethylene moiety. Herein, a novel protocol for the C–F bond etherification of trifluoromethylalkenes and phenols is reported. A variety of alkenyl difluoroaryloxy ethers are obtained with good chemoselectivity and functional group tolerance. DFT calculation results and control experiments suggest that metal ion Cs+ might be involved in this defluorooxylation. Furthermore, the desired product exhibits a good insecticidal activity.
doi_str_mv 10.1021/acs.joc.2c01197
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title Selective C–F Bond Etherification of Trifluoromethylalkenes with Phenols
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