Multielectron Reduction of Esters by a Diazabenzacenaphthenium Photoredox Catalyst
Shintaro Okumura, Shusuke Hattori, Lisa Fang, Yasuhiro Uozumi
Abstract
A novel diazabenzacenaphthenium photocatalyst, N- BAP, with high photoredox abilities and visible-light absorption was designed and prepared in one step. Under visible-light irradiation, N- BAP promoted the four-electron reduction of esters in the presence of ammonium oxalate as a “traceless reductant” to generate carbinol anion intermediates that underwent protonation with water to give the corresponding alcohols. The resulting carbinol anions also exhibited nucleophilic reactivity under the photocatalytic conditions to undergo a 1,2-addition to a second carbonyl compound, affording unsymmetric 1,2-diols.
Topics & Concepts
ChemistryPhotocatalysisProtonationPhotochemistryOxalateCatalysisVisible spectrumPhotoredox catalysisNucleophileReactivity (psychology)Absorption (acoustics)IrradiationNucleophilic additionAmmoniumIonMedicinal chemistryOrganic chemistryAcousticsPathologyOptoelectronicsPhysicsMedicineAlternative medicineNuclear physicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods