Visible-Light-Mediated Decarboxylative (Amino)Alkylation of Azomethine Imines

Herein, we report an efficient, organophotocatalyzed decarboxylative (amino)alkylation of azomethine imines using readily available carboxylic acids as alkylating agents. This transformation exhibits wide scope, and a variety of carboxylic acids, including glycine derivatives, were employed as radical precursors. The use of 4CzIPN as the photocatalyst allowed the application of nonbenzylic secondary and tertiary carboxylic acids also, overcoming previous limitations. The wide scope, applicability of nonprefunctionalized precursors, and mild conditions are the highlights of this method. The intermediacy of key radical intermediates was established by radical trapping experiments.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-07
DOI
https://doi.org/10.1021/acs.joc.5c00159
Citations
1
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.94

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article

Visible-Light-Mediated Decarboxylative (Amino)Alkylation of Azomethine Imines

Anand Singh, Parashuram Sharma, Kirti Khanna, Seshadri Reddy Nasireddy
1 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
0.94
article

Visible-Light-Mediated Decarboxylative (Amino)Alkylation of Azomethine Imines

Anand Singh, Parashuram Sharma, Kirti Khanna, Seshadri Reddy Nasireddy
article en
1 citations

Abstract

Herein, we report an efficient, organophotocatalyzed decarboxylative (amino)alkylation of azomethine imines using readily available carboxylic acids as alkylating agents. This transformation exhibits wide scope, and a variety of carboxylic acids, including glycine derivatives, were employed as radical precursors. The use of 4CzIPN as the photocatalyst allowed the application of nonbenzylic secondary and tertiary carboxylic acids also, overcoming previous limitations. The wide scope, applicability of nonprefunctionalized precursors, and mild conditions are the highlights of this method. The intermediacy of key radical intermediates was established by radical trapping experiments.

The Journal of Organic ChemistryVol. 90(15)
Indian Institute of Technology Kanpur (IN)
Science and Engineering Research Board
Openalex Percentile: Top 27%
Radical Photochemical Reactions
0.94
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