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Updated: May 21, 2025

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Synthesis of Ester-Substituted Polycyclic N-Heteroaromatics via Photocatalyzed Alkoxycarbonylation/Tricyclization
Shan-Shan Zhu1, Zhi-Wei Chen1, Dan-Dan Fan1
1College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China.
Abstract:
For the first time, a photoredox-catalyzed alkoxycarbonylation/tricyclization reaction was developed by employing readily accessible enediynes and alkyloxalyl chlorides as starting materials, enabling the synthesis of ester-substituted polycyclic N-heteroaromatics under mild conditions through a radical-mediated mechanism. This photocatalytic strategy is notable for its exceptional compatibility with diverse functional groups, scalability, and efficiency in the formation of rings and chemical bonds. Notably, continuous flow photocatalysis technology markedly improved these reactions compared to the equivalent batch reactions, efficiently decreasing the reaction times to merely 40 min.
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Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

