Sustainable Cascades to Difluoroalkylated Polycyclic Imidazoles

We reported herein a visible light promoted difluoroalkylated cascade of imidazoles and alkenes to afford highly functionalized polycyclic imidazoles. This method features a direct radical cyclization of imidazoles with alkenes using BrCF2R as radical sources. The reaction conditions tolerate a wide...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-08, Vol.2021 (31), p.4485-4489
Main Authors: Lin, Sheng‐Nan, Chen, Yu, Luo, Xiao‐Dong, Li, Yi
Format: Article
Language:English
Subjects:
Alkenes
Cascade/cyclization
Difluoroalkylation
Imidazole
Photocatalysis
Polycyclic imidazoles
Radicals
Substrates
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Summary:We reported herein a visible light promoted difluoroalkylated cascade of imidazoles and alkenes to afford highly functionalized polycyclic imidazoles. This method features a direct radical cyclization of imidazoles with alkenes using BrCF2R as radical sources. The reaction conditions tolerate a wide range of substrate scope and afford the desired products with up to 95 % isolated yield under mild conditions. Radical‐trapping and light‐on/off experiments indicated a photocatalytic radical mechanism. A sustainable cascade synthesis of imidazoles from alkenes is described here. Series of highly functionalized polycyclic imidazoles were prepared efficiently with 0.01 equiv. of fac‐Ir(ppy)3 as photocatalyst under the irradiation of 3 W blue LEDs. This method is characterized by a wide substrate scope with up to 95 % isolated yield under mild conditions. Mechanistic studies indicated a photocatalyzed direct radical difluoroalkylated cyclization of imidazoles with alkenes.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100868