Nickel/Photoredox Dual-Catalyzed Conversion of Allyl Esters to Ketones via the Formal Deletion of Oxygen
Ryoma Shimazumi, Riku Tanimoto, Mamoru Tobisu
Abstract
We report herein the catalytic conversion of allylic esters into the corresponding ketones by the formal deletion of an oxygen atom. The key to the success of the reaction is the dual use of nickel and photoredox catalysts; the former mediates C–O bond activation and C–C bond formation, while the latter is responsible for deoxygenation of the acyloxy group using PPh 3 as a stoichiometric reductant. Catalytic replacement of an oxygen atom of an allyl ester with a tethered alkene is also accomplished.
Topics & Concepts
ChemistryDeoxygenationCatalysisAllylic rearrangementAlkeneNickelOxygenStoichiometryDouble bondPhotochemistryRutheniumMedicinal chemistryAtom economyAtom (system on chip)Polymer chemistryOrganic chemistryEmbedded systemComputer scienceCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions