α‐Nucleophilic Addition to α,β‐Unsaturated Carbonyl Compounds via Photocatalytically Generated α‐Carbonyl Carbocations

Abstract We report the photocatalytic oxidation of α‐carbonyl radicals of amides or esters to the corresponding α‐carbonyl carbocations through super photoreductant CBZ6 induced redox‐neutral photocatalysis. The α‐carbonyl radicals are formed by the β‐addition of alkyl radicals generated in situ by the photocatalytic fragmentation of N ‐hydroxyphthalimide esters to the α,β‐unsaturated amides and esters. This method enables the α‐nucleophilic addition of hydroxyl or alkoxyl radicals to amides and esters without any prefunctionalization.

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Publication Details

Journal
Angewandte Chemie
Published
2024-11-05
DOI
https://doi.org/10.1002/ange.202415496
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

α‐Nucleophilic Addition to α,β‐Unsaturated Carbonyl Compounds via Photocatalytically Generated α‐Carbonyl Carbocations

J.F. Chen, Zhen‐Zhen Liu, Yan‐Biao Kang, Chong‐Jin Zhang et al.
Angewandte Chemie
Asymmetric Synthesis and Catalysis
article

α‐Nucleophilic Addition to α,β‐Unsaturated Carbonyl Compounds via Photocatalytically Generated α‐Carbonyl Carbocations

J.F. Chen, Zhen‐Zhen Liu, Yan‐Biao Kang, Chong‐Jin Zhang, Jian‐Ping Qu, Fang Wang, Hao Zhang, Yu Sun, Jie Gong
article en

Abstract

Abstract We report the photocatalytic oxidation of α‐carbonyl radicals of amides or esters to the corresponding α‐carbonyl carbocations through super photoreductant CBZ6 induced redox‐neutral photocatalysis. The α‐carbonyl radicals are formed by the β‐addition of alkyl radicals generated in situ by the photocatalytic fragmentation of N ‐hydroxyphthalimide esters to the α,β‐unsaturated amides and esters. This method enables the α‐nucleophilic addition of hydroxyl or alkoxyl radicals to amides and esters without any prefunctionalization.

Angewandte ChemieVol. 137(3)
University of Science and Technology of China (CN), Nanjing Tech University (CN)
National Natural Science Foundation of China, National Key Research and Development Program of China
Openalex Percentile: Top 86%
Asymmetric Synthesis and Catalysis
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