Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with Diazodicarbonyls for Skeleton-Divergent Synthesis of Isocoumarins and Naphthalenes,Organic Letters

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Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with Diazodicarbonyls for Skeleton-Divergent Synthesis of Isocoumarins and Naphthalenes
Organic Letters ( IF 4.9 ) Pub Date : 2022-10-19 , DOI: 10.1021/acs.orglett.2c03288
Weiping Wu ₁ , Xuan Wu ₁ , Shuaixin Fan ₁ , Jin Zhu ₁

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Diversity-oriented synthesis is tremendously useful for expanding the explorable chemical space but restricted by the limited available toolbox of skeleton-diversification chemistry. We report herein Rh(III)-catalyzed coupling of enaminones and diazodicarbonyls for skeleton-divergent synthesis of isocoumarins and naphthalenes. The diazodicarbonyl ring size and pH dependence of the skeleton-forming process demonstrates the achievement of both substrate- and reagent-controlled skeletal diversity generation in a single type of system. An intriguing C–C bond cleavage reactivity is critical for enabling facile synthetic access to isocoumarins.

中文翻译：

Rh(III)-催化烯胺酮导向 C-H 偶联重氮二羰基用于异香豆素和萘的骨架发散合成

面向多样性的合成对于扩展可探索的化学空间非常有用，但受到骨架多样化化学可用工具箱的限制。我们在此报告了 Rh(III) 催化的烯胺酮和重氮二羰基偶联，用于异香豆素和萘的骨架发散合成。骨架形成过程的重氮二羰基环大小和 pH 依赖性证明了在单一类型的系统中实现了底物和试剂控制的骨架多样性产生。有趣的 C-C 键裂解反应性对于能够轻松合成获得异香豆素至关重要。

更新日期：2022-10-19

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