Aromatization-driven deconstruction and functionalization of spiro dihydroquinazolinones via dual photoredox/nickel catalysis is developed. The aromatization effect was introduced to synergistically drive unstrained cyclic C–C bond cleavage, with the aim of overcoming the ring-size limitation of nitrogen-centered radical induced deconstruction of carbocycles. Herein, we demonstrate the synergistic photoredox/nickel catalyzed deconstructive cross-coupling of spiro dihydroquinazolinones with organic halides. Remarkably, structurally diverse organic halides including aryl, alkenyl, alkynyl, and alkyl bromides were compatible for the coupling. In addition, this protocol is also characterized by its mild and redox-neutral conditions, excellent functional group compatibility, high atom economy, and easy scalability. A telescoped procedure involving condensation and ring-opening/coupling was found to be accessible. This work provides a complementary strategy to the existing radical-mediated C–C bond cleavage of unstrained carbocycles.

中文翻译：

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通过双光氧化还原/镍催化芳香化驱动的螺二氢喹唑啉酮解构官能化

开发了通过双光氧化还原/镍催化对螺环二氢喹唑啉酮进行芳香化驱动的解构和官能化。引入芳构化效应来协同驱动无应变环状C-C键断裂，目的是克服以氮为中心的自由基诱导碳环解构的环尺寸限制。在此，我们证明了螺二氢喹唑啉酮与有机卤化物的协同光氧化还原/镍催化解构交叉偶联。值得注意的是，结构多样的有机卤化物（包括芳基、烯基、炔基和烷基溴）适合偶联。此外，该协议还具有条件温和、氧化还原中性、官能团兼容性优异、原子经济性高、易于扩展等特点。发现涉及冷凝和开环/耦合的伸缩程序是可行的。这项工作为现有的自由基介导的无应变碳环 C-C 键断裂提供了补充策略。