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Iron-Catalyzed Radical Intermolecular Addition of Unbiased Alkenes to Aldehydes

Mar Saladrigas, Jordi Puig, Josep Bonjoch, Ben Bradshaw

2020Organic Letters40 citationsDOIOpen Access PDF

Abstract

The intermolecular reductive radical coupling of aldehydes with nonactivated alkenes, employing metal hydride atom transfer (MHAT) catalysis with a combination of FeII and FeIII salts, is described. This constitutes the first use of aldehydes as viable acceptor groups in MHAT reactions. The insights gained in this study led to the reexamination of the previously reported intramolecular version of the reaction, and the addition of FeII salts allowed the development of a more efficient second-generation approach.

Topics & Concepts

ChemistryIntermolecular forceIntramolecular forceCatalysisHydrideRadicalAcceptorPhotochemistryMetalCoupling reactionCombinatorial chemistryMoleculeOrganic chemistryCondensed matter physicsPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions