Catalyst-Free <i>N</i>-Deoxygenation by Photoexcitation of Hantzsch Ester
Mikhail O. Konev, Luana Cardinale, Axel Jacobi von Wangelin
Abstract
A mild and operationally simple protocol for the deoxygenation of a variety of heteroaryl N-oxides and nitroarenes has been developed. A mixture of substrate and Hantzsch ester is proposed to result in an electron donor–acceptor complex, which upon blue-light irradiation undergoes photoinduced electron transfer between the two reactants to afford the products. N-oxide deoxygenation is demonstrated with 22 examples of functionally diverse substrates, and the chemoselective reduction of nitroarenes to the corresponding hydroxylamines is also shown.
Topics & Concepts
DeoxygenationChemistryPhotoexcitationCatalysisElectron transferElectron acceptorPhotochemistrySubstrate (aquarium)AcceptorCombinatorial chemistryOrganic chemistryPhysicsNuclear physicsCondensed matter physicsGeologyExcited stateOceanographyRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions