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Photoinduced copper catalyzed nitrogen-to-alkyl radical relay Sonogashira-type coupling of o-alkylbenzamides with alkynes.
Zhan, Yan-Fang; Chen, Jia-Ming; Sheng, Xia-Xin; Qiu, Chao-Ying; Jiang, Yan; Yang, Sen; Chen, Ming.
Afiliación
  • Zhan YF; Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Chang-zhou University, Changzhou, 213164, China. jy@cczu.edu.cn.
  • Chen JM; Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Chang-zhou University, Changzhou, 213164, China. jy@cczu.edu.cn.
  • Sheng XX; Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Chang-zhou University, Changzhou, 213164, China. jy@cczu.edu.cn.
  • Qiu CY; Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Chang-zhou University, Changzhou, 213164, China. jy@cczu.edu.cn.
  • Jiang Y; Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Chang-zhou University, Changzhou, 213164, China. jy@cczu.edu.cn.
  • Yang S; Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Chang-zhou University, Changzhou, 213164, China. jy@cczu.edu.cn.
  • Chen M; Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Chang-zhou University, Changzhou, 213164, China. jy@cczu.edu.cn.
Chem Commun (Camb) ; 60(61): 7906-7909, 2024 Jul 25.
Article en En | MEDLINE | ID: mdl-38979947
ABSTRACT
This report describes a copper-catalyzed, photoinduced N-to-alkyl radical relay Sonogashira-type reactions at benzylic sites in o-alkylbenzamides with alkynes. The process employs an N-to-alkyl radical mechanism, initiated through the copper-catalyzed reductive generation of nitrogen radicals. Radical translocation is facilitated by a 1,5-hydrogen atom transfer (1,5-HAT), leading to the formation of translocated carbon radicals. These radicals are then subjected to copper-catalyzed alkynylation. The methodology exhibits broad sub-strate scope and applicability to the synthesis of complex natural products.

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Reino Unido

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Commun (Camb) Asunto de la revista: QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Reino Unido