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Selective C-C Bond Scission of Ketones via Visible-Light-Mediated Cerium Catalysis
Chem ( IF 19.1 ) Pub Date : 2019-12-09 , DOI: 10.1016/j.chempr.2019.11.009
Yilin Chen , Jianbo Du , Zhiwei Zuo

Here, we report a general catalytic manifold for the selective C–C bond scission of ketones via the exploitation of the ligand-to-metal charge transfer (LMCT) excitation mode. Through a cooperative utilization of Lewis acid catalysis and LMCT catalysis, the C–C bond of ketones could be selectively and effectively cleaved, enabling the installation of different functionalities at each carbon of the cleaved C–C bond through a sequential and orthogonal manner. This reaction manifold serves as a photocatalytic alternative to the Norrish type I reaction with the combination of visible light and inexpensive cerium salts. Under operationally simple conditions, a wide range of acyclic and cyclic ketones, from simple strained cyclobutanones to complex androsterone with less strained cyclopentanone moiety, could be successfully transformed into versatile chemical building blocks.



中文翻译:

可见光介导的铈催化酮选择性CC键断裂

在这里,我们报告了通过利用配体到金属的电荷转移(LMCT)激发模式对酮进行选择性C–C键断裂的通用催化流形。通过路易斯酸催化和LMCT催化的协同利用,可以选择性,有效地裂解酮的C–C键,从而可以通过顺序和正交的方式在裂解的C–C键的每个碳原子上安装不同的官能团。该反应歧管可结合可见光和廉价的铈盐,作为Norrish I型反应的光催化替代物。在操作简单的条件下,从简单的应变环丁酮到具有较少应变的环戊酮部分的复杂雄甾酮,各种各样的无环和环状酮,

更新日期:2019-12-09
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