Photocatalyzed Amination of Alkyl Halides to Access Primary Amines
Lilian Geniller, Marc Taillefer, Florian Jaroschik, Alexis Prieto
Abstract
We demonstrate that oxime ester derivatives can be used as both a halogen atom transfer (XAT) agent and an imine source under photocatalytic conditions, allowing the radical amination of alkyl halides, resulting in the formation of a broad scope of imines. Hydrolysis of the latter gives direct access to the corresponding primary amines. Mechanistically, the reaction is believed to proceed through the formation of aryl radical intermediates, which are responsible for the activation of alkyl halides via XAT.
Topics & Concepts
ChemistryAminationAlkylHalideImineArylPrimary (astronomy)HalogenCombinatorial chemistryOximeAryl halideOrganic chemistryCatalysisPhysicsAstronomyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions