1,3-Hydro-di/monofluoromethylation of N , N '-Cyclic Azomethine Imines with HCF 2 SO 2 Na/H 2 CFSO 2 Na via Photocatalytic Radical Addition

The radical 1,3-hydro-di/monofluoromethylation of -cyclic azomethine imines with HCF SO Na/H CFSO Na via photoredox catalysis is described. This reaction exhibits broad functional group compatibility, providing the desired products in good yields. However, CF SO Na failed to produce the trifluoromet...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 89; no. 16; pp. 11747 - 11752
Main Authors Kou, Min, Zheng, Jianli, Li, Feifei, Huang, Ling, Cao, Dongdong, Zhong, Aiguo, Yang, Jianguo, Chen, Dingben
Format Journal Article
LanguageEnglish
Published United States 16.08.2024
Online AccessGet full text

Cover

More Information
Summary:The radical 1,3-hydro-di/monofluoromethylation of -cyclic azomethine imines with HCF SO Na/H CFSO Na via photoredox catalysis is described. This reaction exhibits broad functional group compatibility, providing the desired products in good yields. However, CF SO Na failed to produce the trifluoromethyl product. DFT calculations revealed that the transition state activation energy for radical trifluoromethylation was significantly higher and the isotropic charge repulsion makes it difficult for the CF radical to transfer electrons.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00679