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Blue-Light-Induced Iron-Catalyzed α-Alkylation of Ketones

Marie-Samira Abdallah, Nicolas Joly, Sylvain Gaillard, Albert Poater, Jean‐Luc Renaud

2022Organic Letters40 citationsDOI

Abstract

We report a visible-light-induced iron-catalyzed α-alkylation of ketones. The photocatalytic system is based on the single diaminocyclopentadienone iron tricarbonyl complex. Two catalytic intermediates of this complex are able to harvest light, allowing the synthesis of substituted aromatic and aliphatic ketones at room temperature using the borrowing hydrogen strategy in the presence of various substituted primary alcohols as alkylating reagents. Preliminary mechanistic studies unveil the role of light for both the dehydrogenation and reduction step.

Topics & Concepts

AlkylationDehydrogenationChemistryCatalysisReagentPhotocatalysisPrimary (astronomy)Visible spectrumPhotochemistryCombinatorial chemistryOrganic chemistryAstronomyPhysicsOptoelectronicsAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsRadical Photochemical Reactions
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