Oxidative and Redox‐Neutral Approaches to Symmetrical Diamines and Diols by Single Electron Transfer/Hydrogen Atom Transfer Synergistic Catalysis
Masashi Fujita, Fumihisa Kobayashi, Takafumi Ide, Hiromichi Egami, Yoshitaka Hamashima
Abstract
Homocoupling reactions of benzylamines and benzyl alcohols were examined under synergistic catalysis conditions with a photoredox catalyst and thiobenzoic acid as a hydrogen atom abstractor. When pivalaldehyde was used as an electron acceptor, oxidative dimerization proceeded selectively, whereas the use of benzaldehydes or iminium ions as electron acceptors resulted in redox‐neutral coupling. These reactions afforded symmetrical 1,2‐diamines and 1,2‐diols in good yields.
Topics & Concepts
ChemistryIminiumCatalysisHydrogen atomElectron transferRedoxPhotochemistryOxidative coupling of methaneProton-coupled electron transferAcceptorElectron acceptorOxidative phosphorylationOrganic chemistryAlkylPhysicsBiochemistryCondensed matter physicsRadical Photochemical ReactionsCO2 Reduction Techniques and CatalystsOxidative Organic Chemistry Reactions