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Decatungstate/Cobalt Dual Catalyzed Dehydrogenation of Ketones Enabled by Polarity-Matched Site-Selective Activation

Bin Sun, Jia‐Yin Wang, Shuangshuang Zhou, Jiaxing Xu, Xiaohui Zhuang, Zehui Meng, Yifan Xu, Zhiguo Zhang, Can Jin

2024ACS Catalysis37 citationsDOI

Abstract

The direct dehydrogenation of ketones has been widely utilized in both academic and industrial settings as the most efficient means of constructing unsaturated ketones and phenols. In contrast to the induction of dehydrogenation at the α-site of carbonyl by enol activation, direct and efficient activation of the carbonyl β-C(sp 3 )-H bond to form unsaturated ketones remains unexplored. Herein, we report a polarity-matching-based activation strategy for the carbonyl β-C(sp 3 )-H bond, enabling the photoinduced intramolecular dehydrogenation of ketones without prefunctionalization via the merger of photoredox and cobalt catalysis. This photoinduced mode employs a benign and mild approach to construct unsaturated ketone and phenol skeletons via acceptorless catalytic dehydrogenation, showcasing potential applications in the field of drug synthesis.

Topics & Concepts

DehydrogenationCatalysisCobaltPhotochemistryDual (grammatical number)ChemistryPolarity (international relations)Combinatorial chemistryInorganic chemistryOrganic chemistryCellArtBiochemistryLiteratureAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsCarbon dioxide utilization in catalysis
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