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Photoredox/Cobalt-Catalyzed C(sp3)–H Bond Functionalization toward Phenanthrene Skeletons with Hydrogen Evolution
Organic Letters ( IF 4.9 ) Pub Date : 2020-12-08 , DOI: 10.1021/acs.orglett.0c03665
Jia-Dong Guo 1, 2 , Xiu-Long Yang 1, 2 , Bin Chen 1, 2 , Chen-Ho Tung 1, 2 , Li-Zhu Wu 1, 2
Organic Letters ( IF 4.9 ) Pub Date : 2020-12-08 , DOI: 10.1021/acs.orglett.0c03665
Jia-Dong Guo 1, 2 , Xiu-Long Yang 1, 2 , Bin Chen 1, 2 , Chen-Ho Tung 1, 2 , Li-Zhu Wu 1, 2
Affiliation
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The first example of photoredox strategy for synthesis of phenanthrene skeletons through C(sp3)–H functionalization under external oxidant-free conditions is achieved. This transformation relies on the keto–enol tautomerism of 1,3 dicarbonyl moiety, i.e., the enol form of 1,3-dicarbonyl derivatives with relatively lower oxidation potential can be activated by the excited acridinium photocatalyst. The electron and proton eliminated from the substrate are immediately captured by a cobaloxime catalyst to exclusively afford a-carbonyl radical for highly substituted 10-phenanthrenols in good to excellent yields.
中文翻译:
光致氧化还原/钴催化的菲骨架上具有氢演化的C(sp 3)-H键官能化
实现了在外部无氧化剂条件下通过C(sp 3)–H官能化合成菲骨架的光氧化还原策略的第一个例子。这种转化依赖于1,3-二羰基部分的酮-烯醇互变异构现象,即具有较低氧化电位的1,3-二羰基衍生物的烯醇形式可以通过激发的cri啶光催化剂活化。从底物上除去的电子和质子立即被钴肟催化剂捕获,从而以高至优异的产率专门提供了用于高度取代的10-菲基酚的-羰基。
更新日期:2020-12-18
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
光致氧化还原/钴催化的菲骨架上具有氢演化的C(sp 3)-H键官能化
实现了在外部无氧化剂条件下通过C(sp 3)–H官能化合成菲骨架的光氧化还原策略的第一个例子。这种转化依赖于1,3-二羰基部分的酮-烯醇互变异构现象,即具有较低氧化电位的1,3-二羰基衍生物的烯醇形式可以通过激发的cri啶光催化剂活化。从底物上除去的电子和质子立即被钴肟催化剂捕获,从而以高至优异的产率专门提供了用于高度取代的10-菲基酚的-羰基。