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Photochemical reduction of acylimidazolium salts

Lookup NU author(s): Dr Matt HopkinsonORCiD

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Abstract

Light-mediated methodologies for the reduction of acylazolium species generated during N-heterocyclic carbene (NHC)-catalyzed reactions have been developed. Employing the simple amine, DIPEA, as the terminal reductant, products resulting from overall 2-electron or 4-electron-reduction processes could be obtained using either a photocatalytic approach under blue light irradiation or directly under UV-A light irradiation without an additional photocatalyst. Moreover, under the same photocatalyst-free conditions, UV-A-light-mediated reduction could be achieved using triethylsilane as the only reductant with subsequent desilylation and NHC elimination with fluoride delivering the corresponding aldehyde product.

Publication metadata

Author(s): Jakob M, Bechler N, Abdelwahab H, Weber F, Wasternack J, Kleebauer L, Götze JP, Hopkinson MN

Publication type: Article

Publication status: Published

Journal: Beilstein Journal of Organic Chemistry

Year: 2025

Volume: 21

Pages: 1973-1983

Online publication date: 25/09/2025

Acceptance date: 11/09/2025

Date deposited: 07/10/2025

ISSN (print): 2195-951X

ISSN (electronic): 1860-5397

Publisher: Beilstein-Institut

URL: https://doi.org/10.3762/bjoc.21.153

DOI: 10.3762/bjoc.21.153

Data Access Statement: Data generated and analyzed during this study is available from the corresponding author upon reasonable request.

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