Photocatalytic Synthesis of Azetidines and Cyclobutanes via Energy Transfer-Mediated [2 + 2] Cycloaddition

We report a [2 + 2] cycloaddition reaction enabled by triplet energy transfer (EnT) for the efficient construction of four-membered frameworks, including azetidines and cyclobutanes. The reaction proceeds under mild conditions with alkenes bearing biologically relevant motifs, such as 6-azauracil and coumarin, delivering products with excellent diastereo- and regioselectivity. The protocol features operational simplicity, requires no external additives, and affords the desired products in high yields with minimal side reactions.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-11-24
DOI
https://doi.org/10.1021/acs.joc.5c02444
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Photocatalytic Synthesis of Azetidines and Cyclobutanes via Energy Transfer-Mediated [2 + 2] Cycloaddition

Devarajulu Sureshkumar, Koustav Pal, Manasi Mallick
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Photocatalytic Synthesis of Azetidines and Cyclobutanes via Energy Transfer-Mediated [2 + 2] Cycloaddition

Devarajulu Sureshkumar, Koustav Pal, Manasi Mallick
article en

Abstract

We report a [2 + 2] cycloaddition reaction enabled by triplet energy transfer (EnT) for the efficient construction of four-membered frameworks, including azetidines and cyclobutanes. The reaction proceeds under mild conditions with alkenes bearing biologically relevant motifs, such as 6-azauracil and coumarin, delivering products with excellent diastereo- and regioselectivity. The protocol features operational simplicity, requires no external additives, and affords the desired products in high yields with minimal side reactions.

The Journal of Organic ChemistryVol. 90(48)
Indian Institute of Science Education and Research Kolkata (IN)
Openalex Percentile: Top 73%
Radical Photochemical Reactions
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