Issue 11, 2024
From the journal:

Organic Chemistry Frontiers

Photochemical [2 + 2 + 1] annulation of 2-vinyloxy arylalkynes with bromomalonates via energy transfer†

Shuo Tang,‡a   Jiupeng Liu,‡a   Min Zhang,a   Dan Wang,a   Yong Wang, ORCID logo *a   Jingjing Zhao*a  and  Pan Li ORCID logo *a  

* Corresponding authors

a College of Chemistry and Molecular Sciences, Henan University, Kaifeng 475004, P. R. China
E-mail: wangyong@henu.edu.cn, zhaojingjing@henu.edu.cn, panli@henu.edu.cn

Abstract

A photochemical [2 + 2 + 1] radical annulation of 2-vinyloxy arylalkynes with bromomalonates has been developed. This protocol affords a transition-metal-free, oxidant-free and base-free approach to cyclopenta[b]benzofurans under mild conditions. This tandem reaction involves sequential radical addition, 5-exo-dig cyclization, 1,5-H shift, 5-endo-trig annulation, radical coupling, and elimination processes. Significantly, the photoinduced C–Br bond homolysis of bromomalonates involves an energy transfer, and the solvent DMF acts as an acid-binding reagent.

Graphical abstract: Photochemical [2 + 2 + 1] annulation of 2-vinyloxy arylalkynes with bromomalonates via energy transfer

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Article information

DOI
https://doi.org/10.1039/D4QO00249K
Article type
Research Article
Submitted
05 Feb 2024
Accepted
14 Apr 2024
First published
16 Apr 2024

Org. Chem. Front., 2024,11, 3160-3164

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Photochemical [2 + 2 + 1] annulation of 2-vinyloxy arylalkynes with bromomalonates via energy transfer

S. Tang, J. Liu, M. Zhang, D. Wang, Y. Wang, J. Zhao and P. Li, Org. Chem. Front., 2024, 11, 3160 DOI: 10.1039/D4QO00249K

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