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Light‐Driven Intramolecular C−N Cross‐Coupling via a Long‐Lived Photoactive Photoisomer Complex
Author(s) -
Jing Dong,
Lu Cong,
Chen Zhuo,
Jin Songyang,
Xie Lijuan,
Meng Ziyi,
Su Zhishan,
Zheng Ke
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201906112
Subject(s) - rutaecarpine , quinazolinone , intramolecular force , chemistry , photochemistry , substrate (aquarium) , electron paramagnetic resonance , combinatorial chemistry , stereochemistry , physics , oceanography , chromatography , nuclear magnetic resonance , geology
Reported herein is a visible‐light‐driven intramolecular C−N cross‐coupling reaction under mild reaction conditions (metal‐ and photocatalyst‐free, at room temperature) via a long‐lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N ‐substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram‐scale synthesis and solar‐driven transformation, as well as promising tumor‐suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV‐vis spectroscopy, EPR, and X‐ray single‐crystal structure of the key intermediate, provides insight into the mechanism.