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. 2025 May 8;15(19):15155-15163.
doi: 10.1039/d5ra02540k. eCollection 2025 May 6.

Electron donor-acceptor complex-driven photocatalyst-free synthesis of nitrocyclopropanes

Paula Pérez-Ramos  1 , Patrícia I C Godinho  1 , Raquel G Soengas  1 , Humberto Rodríguez-Solla  1
Affiliations

Electron donor-acceptor complex-driven photocatalyst-free synthesis of nitrocyclopropanes

Paula Pérez-Ramos et al. RSC Adv. .

Abstract

Herein, a visible light-promoted metal-free protocol for the synthesis of nitrocyclopropanes under mild conditions is reported. Specifically, the process is driven by the photochemical activity of ternary EDA complexes formed upon complexation of α-bromonitrostyrenes and DIPEA in the presence of benzaldehyde. This reaction provides a variety of densely functionalized cyclopropanes with good selectivity under mild reaction conditions. Mechanistic investigations on the aspects of the process also demonstrate formation of the hypothesized EDA complex.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Methods for the photocatalytic construction of cyclopropanes from Michael acceptors.
Scheme 2
Scheme 2. Proposed mechanism for the EDA complex-driven cyclopropanation strategy.
Scheme 3
Scheme 3. Organocatalytic ring-opening reaction of nitrocyclopropanes 2a/2a′.
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