Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines
Hannah E. Askey, James D. Grayson, Joshua D. Tibbetts, Jacob C. Turner-Dore, Jake M. Holmes, Gabriele Kociok‐Köhn, Gail L. Wrigley, Alexander J. Cresswell
Abstract
-arylation to provide a general and modular access to valuable (spirocyclic) 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydronaphthyridines. Mechanistic and kinetic studies support an irreversible hydrogen atom transfer activation of the alkylamine by the azidyl radical and some contribution from a radical chain. The reaction is photon-limited and exhibits a zero-order dependence on amine, azide, and photocatalyst, with a first-order dependence on styrene.
Topics & Concepts
ChemistryCombinatorial chemistryCatalysisPhotoredox catalysisPhotocatalysisIntramolecular forceAmine gas treatingAryl radicalArylAminationLeaving groupReactive intermediatePhotochemistryOrganic chemistryAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions