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C3 Selective chalcogenation and fluorination of pyridine using classic Zincke imine intermediates.
Li, Shun; Tang, Juan; Shi, Yonglin; Yan, Meixin; Fu, Yihua; Su, Zhishan; Xu, Jiaqi; Xue, Weichao; Zheng, Xueli; Ge, Yicen; Li, Ruixiang; Chen, Hua; Fu, Haiyan.
Afiliación
  • Li S; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Tang J; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Shi Y; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Yan M; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Fu Y; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Su Z; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Xu J; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Xue W; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Zheng X; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Ge Y; College of Materials, Chemistry and Chemical Engineering, Chengdu University of Technology, Chengdu, Sichuan, 610059, PR China.
  • Li R; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China.
  • Chen H; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China. scuhchen@scu.edu.cn.
  • Fu H; Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, 610064, PR China. scufhy@scu.edu.cn.
Nat Commun ; 15(1): 7420, 2024 Aug 28.
Article en En | MEDLINE | ID: mdl-39198410
ABSTRACT
Regioselective C-H functionalization of pyridines remains a persistent challenge due to their inherent electronically deficient properties. In this report, we present a strategy for the selective pyridine C3-H thiolation, selenylation, and fluorination under mild conditions via classic N-2,4-dinitrophenyl Zincke imine intermediates. Radical inhibition and trapping experiments, as well as DFT theoretical calculations, indicated that the thiolation and selenylation proceeds through a radical addition-elimination pathway, whereas fluorination via a two-electron electrophilic substitution pathway. The pre-installed electron-deficient activating N-DNP group plays a crucial and positive role, with the additional benefit of recyclability. The practicability of this protocol was demonstrated in the gram-scale synthesis and the late-stage modification of pharmaceutically relevant pyridines.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Nat Commun Asunto de la revista: BIOLOGIA / CIENCIA Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Nat Commun Asunto de la revista: BIOLOGIA / CIENCIA Año: 2024 Tipo del documento: Article Pais de publicación: Reino Unido