Regioselective Aminomethylation and Benzylation of N -Heterocycles via Controllable Cleavage of Triazinanes under Ambient Conditions

Abstract A site-selective reaction for the aminomethylation of imidazoheterocycles is developed using photoredox catalysis under mild conditions. A complementary metal free HFIP promoted reaction is also developed which gives corresponding anilines in good yields. Metal free conditions, scalability, less use of triazinanes, use of recyclable solvents, and ease of operation are the advantages of the developed protocol. Mechanistic studies were conducted to elucidate the mechanism underlying the alkylation reactions. Moreover, solvent recycling experiment has also been carried out to highlight the sustainability of the developed protocol.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-10-06
DOI
https://doi.org/10.1021/acs.joc.6c01570
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Regioselective Aminomethylation and Benzylation of N -Heterocycles via Controllable Cleavage of Triazinanes under Ambient Conditions

Abhinay S. Chillal, Umesh A. Kshirsagar, Mahesh Sasamal, Varsha Kumari
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Regioselective Aminomethylation and Benzylation of N -Heterocycles via Controllable Cleavage of Triazinanes under Ambient Conditions

Abhinay S. Chillal, Umesh A. Kshirsagar, Mahesh Sasamal, Varsha Kumari
article en

Abstract

Abstract A site-selective reaction for the aminomethylation of imidazoheterocycles is developed using photoredox catalysis under mild conditions. A complementary metal free HFIP promoted reaction is also developed which gives corresponding anilines in good yields. Metal free conditions, scalability, less use of triazinanes, use of recyclable solvents, and ease of operation are the advantages of the developed protocol. Mechanistic studies were conducted to elucidate the mechanism underlying the alkylation reactions. Moreover, solvent recycling experiment has also been carried out to highlight the sustainability of the developed protocol.

The Journal of Organic Chemistry
Indian Institute of Technology Indore (IN)
Openalex Percentile: Top 23%
Radical Photochemical Reactions
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