Photoredox/NHC Dual Catalysis Enabled de Novo Synthesis of α-Amino Acids Derivatives

Herein, we report a mild and operationally simple photoredox/NHC dual catalysis strategy for the α-carboxylation of tertiary amine C(sp<sup>3</sup>)-H bonds using diethyl pyrocarbonate. This method offers a novel approach for synthesizing α-amino acid derivatives. The protocol features a broad substrate scope, accommodating both N-aryl tetrahydroisoquinolines (THIQ) and <i>N</i>-methyl aniline and is scalable to gram quantities. Additionally, it is suitable for the late-stage derivatization of certain pharmaceutical compounds.

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Publication Details

Journal
Organic Letters
Published
2024-09-23
DOI
https://doi.org/10.1021/acs.orglett.4c03387
Citations
7
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.75

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Photoredox/NHC Dual Catalysis Enabled de Novo Synthesis of α-Amino Acids Derivatives

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7 citations
Organic Letters
Radical Photochemical Reactions
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article

Photoredox/NHC Dual Catalysis Enabled de Novo Synthesis of α-Amino Acids Derivatives

Chenxing Zhou, Youwan Ye, Yong Yuan, Congde Huo, Xiazhen Bao, Xin Zhang, Dongsheng Ji
article en
7 citations

Abstract

Herein, we report a mild and operationally simple photoredox/NHC dual catalysis strategy for the α-carboxylation of tertiary amine C(sp<sup>3</sup>)-H bonds using diethyl pyrocarbonate. This method offers a novel approach for synthesizing α-amino acid derivatives. The protocol features a broad substrate scope, accommodating both N-aryl tetrahydroisoquinolines (THIQ) and <i>N</i>-methyl aniline and is scalable to gram quantities. Additionally, it is suitable for the late-stage derivatization of certain pharmaceutical compounds.

Organic LettersVol. 26(39)
Northwest Normal University (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation
Openalex Percentile: Top 16%
Radical Photochemical Reactions
1.75
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