Cooperative photoactivation/Lewis base catalyzed [4 + 2] annulations of α-diazoketones and ortho-amino MBH carbonates to access dihydroquinolinone frameworks,Organic Chemistry Frontiers

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Cooperative photoactivation/Lewis base catalyzed [4 + 2] annulations of α-diazoketones and ortho-amino MBH carbonates to access dihydroquinolinone frameworks
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2023-01-10 , DOI: 10.1039/d2qo01974d
Jin Zhou ₁ , Chen Chen ₁ , Qiwen Pang ₁ , Wei-Fang Zuo ₁ , Xiang Li ₁ , Gu Zhan ₁ , Qian-Qian Yang ₁ , Bo Han ₁

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A series of multifunctional dihydroquinolinone frameworks have been synthesized via synergistic catalysis combining photolysis and Lewis base catalysis utilizing in situ generated ketenes from the visible-light-mediated Wolff rearrangement of α-diazoketones and ortho-amino MBH carbonates. This powerful [4 + 2] annulation further broadens the application of MBH carbonates in cooperative catalysis and features good compatibility and high efficiency. Furthermore, the control experiments indicate that a synergistic catalysis strategy plays a crucial role in the cycloaddition reaction, and a plausible mechanism is proposed to explain the reaction process.

中文翻译：

协同光活化/路易斯碱催化 [4 + 2] α-重氮酮和邻氨基 MBH 碳酸盐的环化以获得二氢喹啉酮框架

通过结合光解和路易斯碱催化的协同催化，利用可见光介导的 α-重氮酮和邻氨基 MBH 碳酸盐的沃尔夫重排原位生成的乙烯酮，合成了一系列多功能二氢喹啉酮骨架。这种强大的[4 + 2]环化进一步拓宽了MBH碳酸盐在协同催化中的应用，具有良好的相容性和高效性。此外，控制实验表明，协同催化策略在环加成反应中起着至关重要的作用，并提出了一个似是而非的机制来解释反应过程。

更新日期：2023-01-10

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