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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Intramolecular Dearomative [2 + 2] Cycloadditions of (Hetero)arenes Utilizing an Energy-Transfer Organic
Xuning Li1, Tian-Yu Sun2, Xiao-Feng Xia1
1Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu214122, China.
Abstract:
Expanding the application scope of organic photoredox catalysts is of considerable importance in photocatalysis. Herein, we report an energy transfer (EnT)-mediated intramolecular dearomative [2+2] cycloaddition of N-substituted-N-(2-arylallyl)-2-naphthamides, N-acryloyl-N-substituted α/β-naphthamides, and benzoheterocycles using an easily accessible phenothiazine-derived organic photocatalyst. This transformation proceeds under mild conditions and provides efficient access to structurally complex polycyclic frameworks. DFT studies reveal that the photocatalyst plays a pivotal role in facilitating the reaction through the formation of a triplet exciplex between the substrate and the triplet-state photocatalyst.
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