Photochemical, Catalyst-Free [2+2] Cycloaddition of Coumarin-3-carboxylates with Alkenes

Herein, we report a visible light-promoted, photocatalyst-free [2+2] photocycloaddition of coumarin-3-carboxylates with alkenes, resulting in an expeditious and efficient synthesis of cyclobutane-fused coumarins. The reaction was demonstrated on a gram scale and can also be performed under solar irradiation. The wide substrate scope, short reaction times, and high yields are highlights of this method. Preliminary mechanistic studies indicate that the reaction occurs through the involvement of an excited triplet state intermediate.

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Publication Details

Journal
Organic Letters
Published
2025-12-08
DOI
https://doi.org/10.1021/acs.orglett.5c04113
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Photochemical, Catalyst-Free [2+2] Cycloaddition of Coumarin-3-carboxylates with Alkenes

Anand Singh, Nisha Rawat, Parashuram Sharma, Seshadri Reddy Nasireddy et al.
Organic Letters
Radical Photochemical Reactions
article

Photochemical, Catalyst-Free [2+2] Cycloaddition of Coumarin-3-carboxylates with Alkenes

Anand Singh, Nisha Rawat, Parashuram Sharma, Seshadri Reddy Nasireddy, Riya Sikdar
article en

Abstract

Herein, we report a visible light-promoted, photocatalyst-free [2+2] photocycloaddition of coumarin-3-carboxylates with alkenes, resulting in an expeditious and efficient synthesis of cyclobutane-fused coumarins. The reaction was demonstrated on a gram scale and can also be performed under solar irradiation. The wide substrate scope, short reaction times, and high yields are highlights of this method. Preliminary mechanistic studies indicate that the reaction occurs through the involvement of an excited triplet state intermediate.

Organic LettersVol. 27(50)
Indian Institute of Technology Kanpur (IN)
Openalex Percentile: Top 71%
Radical Photochemical Reactions
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