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Approach to Access Benzo[j]phenanthridinones from 1,7-Enynes and Aryldiazonium Salts via a Domino Radical Relay Process Enabled by a P/N-Heteroleptic Cu(I)-Photosensitizer.
Xiang, Siwei; Ni, Qibo; Liu, Qian; Zhou, Sicheng; Wang, Huihui; Zhou, Yan; Liu, Yunkui.
Afiliación
  • Xiang S; State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.
  • Ni Q; State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.
  • Liu Q; State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.
  • Zhou S; State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.
  • Wang H; State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.
  • Zhou Y; State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.
  • Liu Y; State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China.
J Org Chem ; 88(18): 13248-13261, 2023 Sep 15.
Article en En | MEDLINE | ID: mdl-37616100
A mild approach for the synthesis of benzo[j]phenanthridin-6(5H)-one derivatives from 1,7-enynes and aryldiazonium salts has been successfully developed involving a domino radical relay process enabled by a heteroleptic Cu(I)-photosensitizer under visible-light-driven photocatalytic conditions. Mechanistic studies disclosed that the oxidative quenching of the excited state of PS 4 with aryldiazonium salts via an SET process generated aryl radicals, which could play a radical initiator-terminator dual role within the whole radical relay process, namely, at the initial step acting as a radical donor to trigger the radical addition to the olefin moieties of 1,7-enynes while at the final stage serving as a radical acceptor to complete the cyclization.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2023 Tipo del documento: Article Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2023 Tipo del documento: Article Pais de publicación: Estados Unidos