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Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

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journal contribution
posted on 09.07.2020, 20:29 by José Tiago M. Correia, Gustavo Piva da Silva, Camila M. Kisukuri, Elias André, Bruno Pires, Pablo S. Carneiro, Márcio W. Paixão
A metal- and photocatalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a single electron transfer (SET) event involving a photoexcited electron-donor–acceptor complex between an NHPI ester and a Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. The method provides an operationally simple, robust, and step-economical approach toward the construction of diversely functionalized dihydroquinolinones bearing quaternary centers. A sequential one-pot hydroalkylation–isomerization approach is also offered, giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance were observed in both approaches.