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.

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Reported herein is avisible-light-driven intramolecular CÀNc ross-coupling reaction under mild reaction conditions (metal-and photocatalyst-free,a tr oom temperature) via al ong-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with ab road substrate scope (> 50 examples) and further exploited to synthesizethe natural products tryptanthrin, rutaecarpine,a nd their analogues.T he success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity,p roves the potential of this strategy for practical applications.M echanistic investigations,i ncluding control experiments,D FT calculations,U V-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism. Scheme 1. a) Photoactive EDA complexesa sphotosensitizers. b) Photoisomerization in organic synthesis. c) CÀNbond formation via longlived photoactive photoisomerc omplexes.

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