Issue 1, 2024

Photocatalytic (3 + 2) dipolar cycloadditions of aziridines driven by visible-light

Abstract

Herein, we document the design and development of a novel (3 + 2) cycloaddition reaction aided by the activity of an organic photocatalyst and visible light. The process is extremely fast, taking place in a few minutes, with virtually complete atom economy. A large variety of structurally diverse aziridines were used as masked ylides in the presence of different types of dipolarophiles (28 examples with up to 94% yield and >95 : 5 dr). Mechanistic insights obtained from photophysical, electrochemical and experimental studies highlight that the chemistry is driven by the in situ generation of the reactive ylide through two consecutive electron-transfer processes. We also report an aerobic cascade process, where an additional oxidation step grants access to a vast array of pyrrole derivatives (19 examples with up to 95% yield). Interestingly, the extended aromatic core exhibits a distinctive absorption and emission profile, which can be easily used to tag the effectiveness of this covalent linkage.

Graphical abstract: Photocatalytic (3 + 2) dipolar cycloadditions of aziridines driven by visible-light

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Article information

Article type
Edge Article
Submitted
08 11月 2023
Accepted
29 11月 2023
First published
29 11月 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 271-277

Photocatalytic (3 + 2) dipolar cycloadditions of aziridines driven by visible-light

D. Mazzarella, T. Bortolato, G. Pelosi and L. Dell'Amico, Chem. Sci., 2024, 15, 271 DOI: 10.1039/D3SC05997A

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