Energy Transfer Photocatalytic Radical Rearrangement in <i>N</i>-Indolyl Carbonates
Milan Bera, Ho Seong Hwang, Tae‐Woong Um, Soo Min Oh, Seunghoon Shin, Eun Jin Cho
Abstract
A new type of sp3-like N-centered radical has been generated by selective energy transfer catalysis. Upon photoexcitation, homolytic N–O bond cleavage of N-indolyl carbonate in the presence of an Ir complex produced N- and O-centered radicals. The high spin density at the C3 position of indole led to radical recombination with the O-centered radical, affording valuable 3-oxyindole derivatives without decarboxylation. Transformations of the desired products into various molecules were also demonstrated.
Topics & Concepts
ChemistryRadicalDecarboxylationPhotochemistryIndole testHomolysisPhotoexcitationBond cleavageCatalysisPhotocatalysisMoleculeExcited stateStereochemistryOrganic chemistryPhysicsNuclear physicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques