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通过协同的铜/钯催化炔烃的硼二氟乙烯基化反应合成 -二氟代 1,3-二烯。

Synthesis of -Difluorinated 1,3-Dienes via Synergistic Cu/Pd-Catalyzed Borodifluorovinylation of Alkynes.

机构信息

Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China.

Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, Center for Excellence in Molecular Synthesis of CAS, University of Science and Technology of China, Hefei, Anhui 230026, People's Republic of China.

出版信息

Org Lett. 2022 Aug 19;24(32):5884-5889. doi: 10.1021/acs.orglett.2c01875. Epub 2022 Aug 4.

Abstract

-Difluoroalkenes (=CF), which normally act as metabolically stable bioisosteres for carbonyl groups (C═O), are widely applied in agrochemicals and pharmaceuticals and are also used as building blocks in organic synthesis. Herein, an example of Cu/Pd-catalyzed borodifluorovinylation was achieved using alkynes, difluoroethylene bromide, and Bpin as chemical feedstocks, providing the corresponding conjugated -difluoroalkene scaffold with good functional group compatibility. Moreover, an array of fluorinated synthons can be obtained through further transformations.

摘要

二氟烯烃(=CF)通常作为羰基(C=O)的代谢稳定的生物等排体,广泛应用于农用化学品和药物中,也可用作有机合成中的构建块。在此,使用炔烃、二氟乙烯溴化物和 Bpin 作为化学原料,实现了铜/钯催化的硼二氟乙烯基化反应,为具有良好官能团兼容性的相应共轭 -二氟烯烃支架提供了可能性。此外,还可以通过进一步的转化获得一系列氟化合成子。

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