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Synthesis of C(3) SCF3-Substituted Pyrrolidinoindoline by PIII/PV Redox Catalysis Using CF3SO2Cl as Electrophilic CF3S Reagent.
Yu, Yi-Han; Sun, Gang; Zhao, Di; Wu, Yi-Kai; Yuan, Haoliang; Wen, Xiaoan; Liu, Liu; Xu, Qing-Long.
Afiliação
  • Yu YH; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Longmian Dadao, Nanjing 211198, China.
  • Sun G; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Longmian Dadao, Nanjing 211198, China.
  • Zhao D; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Longmian Dadao, Nanjing 211198, China.
  • Wu YK; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Longmian Dadao, Nanjing 211198, China.
  • Yuan H; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Longmian Dadao, Nanjing 211198, China.
  • Wen X; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Longmian Dadao, Nanjing 211198, China.
  • Liu L; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Longmian Dadao, Nanjing 211198, China.
  • Xu QL; Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 639 Longmian Dadao, Nanjing 211198, China.
J Org Chem ; 2024 Aug 04.
Article em En | MEDLINE | ID: mdl-39097903
ABSTRACT
This work reports a method for the catalytic synthesis of C(3) SCF3-substituted pyrrolidinindoline using a small-ring organophosphorus-based catalyst and a hydrosilane reductant, with trifluoromethanesulfonyl chloride as the electrophilic SCF3 reagent. This method can drive the conversion of tryptamine to the C(3) SCF3-substituted pyrrolidine indoline. The readily available, inexpensive trifluoromethanesulfonyl chloride could be activated as an electrophilic SCF3 source by PIII/PV redox catalysis and could efficiently participate in the reaction of tryptamines, thus providing various substituted C(3) SCF3-substituted pyrrolidinoindoline in moderate to excellent yields. This presented strategy features a broad substrate scope, and the structure has value for in-depth research.

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2024 Tipo de documento: Article País de afiliação: China

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2024 Tipo de documento: Article País de afiliação: China