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Copper-catalyzed radical-mediated intermolecular cyanomonofluoroalkylation of alkenes and alkynes.
Cui, Xuhui; Wang, Xia; Huang, Yanlan; Jiang, Qi; Liu, Li; Wang, Yanzhao; Wu, Jingjing; Wu, Fanhong.
Affiliation
  • Cui X; School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.
  • Wang X; School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.
  • Huang Y; School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.
  • Jiang Q; School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.
  • Liu L; School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.
  • Wang Y; School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.
  • Wu J; Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai Institute of Technology, Shanghai 201418, China. wfh@sit.edu.cn.
  • Wu F; School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, China.
Org Biomol Chem ; 21(16): 3447-3452, 2023 Apr 26.
Article in En | MEDLINE | ID: mdl-37039316
ABSTRACT
A novel copper-catalyzed three-component reaction of monofluoroalkylation agents, alkenes and TMSCN is described. In addition, alkynes could also be compatible with the reaction system to obtain three-component products for the first time with moderate yield and excellent E/Z stereoselectivity. This reaction provides a facile method for the synthesis of cyanomonofluoroalkyl compounds, which may serve as potentially useful organic intermediates for further transformations. Preliminary mechanistic investigation indicated that monofluoroalkyl free radicals were involved in the cyanomonofluoroalkylation process.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2023 Document type: Article Affiliation country: China
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2023 Document type: Article Affiliation country: China