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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
Published on: November 29, 2018
Photoinduced remote C-N/C bond formation via ring-opening 1,4-difunctionalization of methylenecyclobutanes
Yan Zhang1, Yahong Chen1, Yecai Liu1
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Key Laboratory of Advanced Catalysis and Adsorption Materials, Zhejiang Normal University Jinhua 321004 China zhangyan001@zjnu.edu.cn.
Abstract:
The construction of C-N bonds is a fundamental transformation in organic synthesis. While significant progress has been made in C-N bond formation at the alkene π-bond or at the allylic position, achieving remote C-N bond formation remains a considerable challenge. Herein, we report a photochemical strategy for remote 1,4-difunctionalization to forge C-N bonds, enabled by strain-induced ring-opening of methylenecyclobutanes. Using pyrazole or acetonitrile as nitrogen nucleophiles, this method delivers a range of bishomoallylic amine derivatives. Notably, the protocol is also extendable to C-C bond formation with carbon nucleophiles, including pyrroles, indoles, naphthol, and electron-rich arenes.
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