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

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...

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Veröffentlicht in:Journal of organic chemistry 2024-08, Vol.89 (16), p.11747-11752
Hauptverfasser: Kou, Min, Zheng, Jianli, Li, Feifei, Huang, Ling, Cao, Dongdong, Zhong, Aiguo, Yang, Jianguo, Chen, Dingben
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container_end_page 11752
container_issue 16
container_start_page 11747
container_title Journal of organic chemistry
container_volume 89
creator Kou, Min
Zheng, Jianli
Li, Feifei
Huang, Ling
Cao, Dongdong
Zhong, Aiguo
Yang, Jianguo
Chen, Dingben
description 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.
doi_str_mv 10.1021/acs.joc.4c00679
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title 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
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