Visible‐Light‐Mediated Energy Transfer Enables the Synthesis of β‐Lactams via Intramolecular Hydrogen Atom Transfer
Meghan J. Oddy, Daniel A. Kusza, Ryan G. Epton, Jason M. Lynam, William P. Unsworth, Wade F. Petersen
Abstract
Abstract The synthesis of 2‐azetidinones (β‐lactams) from simple acrylamide starting materials by visible‐light‐mediated energy transfer catalysis is reported. The reaction features a C(sp 3 )−H functionalization via a variation of the Norrish–Yang photocyclization involving a carbon‐to‐carbon 1,5‐hydrogen atom transfer (supported by deuterium labelling and DFT calculations) and can be used for the construction of a diverse range of β‐lactam products.
Topics & Concepts
Intramolecular forceHydrogen atomPhotochemistryChemistryCatalysisDeuteriumSurface modificationAtom (system on chip)Carbon fibersMaterials scienceStereochemistryPhysical chemistryOrganic chemistryAtomic physicsEmbedded systemPhysicsComposite numberAlkylComposite materialComputer scienceSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions