Light-Driven N-Heterocyclic Carbene-Catalyzed Multi-Component Reaction for the Synthesis of β-Amino Ketones

A N-heterocyclic carbene-catalyzed (NHC) three-component reaction involving <i>N</i>-aminopyridinium salts, alkenes, and aldehydes for the synthesis of β-amino ketones is described. In this reaction, <i>N</i>-aminopyridinium salts and the Breslow intermediate, which is generated from NHC and aldehydes, are utilized to undergo a single-electron transfer process, forming a ketyl radical intermediate and amidyl radicals. Subsequent to the formation of the amidyl radical, it undergoes selective capture by alkenes, followed by radical cross-coupling to yield the desired β-amino ketones.

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Publication Details

Journal
Organic Letters
Published
2024-10-08
DOI
https://doi.org/10.1021/acs.orglett.4c03288
Citations
6
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.50

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article

Light-Driven N-Heterocyclic Carbene-Catalyzed Multi-Component Reaction for the Synthesis of β-Amino Ketones

Wujiong Xia, Chengcheng Shi, Lin Guo, Chao Yang et al.
6 citations
Organic Letters
Catalytic C–H Functionalization Methods
1.50
article

Light-Driven N-Heterocyclic Carbene-Catalyzed Multi-Component Reaction for the Synthesis of β-Amino Ketones

Wujiong Xia, Chengcheng Shi, Lin Guo, Chao Yang, Jiawen Yin, Nan Zhong
article en
6 citations

Abstract

A N-heterocyclic carbene-catalyzed (NHC) three-component reaction involving <i>N</i>-aminopyridinium salts, alkenes, and aldehydes for the synthesis of β-amino ketones is described. In this reaction, <i>N</i>-aminopyridinium salts and the Breslow intermediate, which is generated from NHC and aldehydes, are utilized to undergo a single-electron transfer process, forming a ketyl radical intermediate and amidyl radicals. Subsequent to the formation of the amidyl radical, it undergoes selective capture by alkenes, followed by radical cross-coupling to yield the desired β-amino ketones.

Organic LettersVol. 26(41)
Harbin Institute of Technology (CN), Henan Normal University (CN)
Science and Technology Foundation of Shenzhen City, National Natural Science Foundation of China, Natural Science Foundation of Guangdong Province, State Key Laboratory of Urban Water Resource and Environment, Basic and Applied Basic Research Foundation of Guangdong Province
Openalex Percentile: Top 19%
Catalytic C–H Functionalization Methods
1.50
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