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Rhodium-Catalyzed Deoxygenation and Borylation of Ketones: A Combined Experimental and Theoretical Investigation

Lei Tao, Xueying Guo, Jie Li, Ruoling Li, Zhenyang Lin, Wanxiang Zhao

2020Journal of the American Chemical Society64 citationsDOI

Abstract

have been developed, leading to efficient formation of alkenes, vinylboronates, and vinyldiboronates. These reactions feature mild reaction conditions, a broad substrate scope, and excellent functional-group compatibility. Mechanistic studies support that the ketones initially undergo a Rh-catalyzed deoxygenation to give alkenes via boron enolate intermediates, and the subsequent Rh-catalyzed dehydrogenative borylation of alkenes leads to the formation of vinylboronates and diboration products, which is also supported by density functional theory calculations.

Topics & Concepts

BorylationChemistryRhodiumDeoxygenationCatalysisBoronPhotochemistryOrganic chemistryArylAlkylOrganoboron and organosilicon chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions
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