Visible-Light-Induced Monofluoroalkenylation and gem-Difluoroallylation of Inactivated C(sp3)–H Bonds via 1,5-Hydrogen Atom Transfer (HAT)

The direct monofluoroalkenylation of C­(sp3)–H bonds is of great importance and quite challenging. Current methods have been restricted to the monofluoroalkenylation of activated C­(sp3)–H bonds. Here, we reported the photocatalyzed C­(sp3)–H monofluoroalkenylation of inactivated C­(sp3)–H bonds wit...

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Veröffentlicht in:Journal of organic chemistry 2023-03, Vol.88 (6), p.3883-3896
Hauptverfasser: Bao, Yanyang, Tang, Meifang, Wang, Qing, Cao, Zhong-Yan, Wang, Yanan, Yuan, Zheliang
Format: Artikel
Sprache:eng
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Zusammenfassung:The direct monofluoroalkenylation of C­(sp3)–H bonds is of great importance and quite challenging. Current methods have been restricted to the monofluoroalkenylation of activated C­(sp3)–H bonds. Here, we reported the photocatalyzed C­(sp3)–H monofluoroalkenylation of inactivated C­(sp3)–H bonds with gem-difluoroalkenes via 1,5-hydrogen atom transfer. This process shows good functional group tolerance, such as halides (F, Cl), nitrile, sulfone, ester, and pyridine, and good γ-selectivity. Moreover, this method succeeds in the photocatalyzed gem-difluoroallylation of inactivated C­(sp3)–H with α-trifluoromethyl alkenes.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00144