著者

西本 能弘 安田 誠

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.80, no.11, pp.1000-1010, 2022-11-01 (Released:2022-11-05)

参考文献数

117

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In recent years, carbon-fluorine (C-F) bond transformation for organic synthesis has been remarkably developed. Herein, we describe four types of C-F bond transformation mediated by Lewis acids: (1) C(sp2)-F bond transformation of gem-difluoroalkenes through oxyindation/β-fluorine elimination to afford fluorinated isocoumarins; (2) B(C6F5)3-catalyzed substitution of fluorine in 1-fluorostyrenes with silyl ketene acetals via abstraction of F− by in situ generated silylium ions; (3) BF3-catalyzed formal insertion of diazoesters into the C-F bonds of benzylic fluorides; and, (4) photoredox catalyst/Lewis acidic Sn species-mediated C(sp3)-F bond allylation of perfluoroalkylarenes. Density functional theory (DFT) study of the reaction mechanisms suggests the importance of choosing the appropriate Lewis acid to achieve an appropriate activation method for the C-F bonds in each reaction.