Photocatalytic <i>para</i>-Selective C–H Functionalization of Anilines with Diazomalonates
Ujjwal Karmakar, Ho Seong Hwang, Yunjeong Lee, Eun Jin Cho
Abstract
Visible-light-induced para-selective C–H functionalization of anilines over N–H insertion was developed using diazomalonates with the help of an Ir(III) photocatalyst. The para-selective radical–radical cross coupling proceeded via C-centered radical intermediates generated from both anilines and diazomalonates. The photochemistry of anilines could be extended to other N-heterocycles, such as indole and carbazole. The reaction pathway for the selective C–C coupling was validated by electrochemical and photophysical experiments as well as computational studies.
Topics & Concepts
Surface modificationChemistryPhotocatalysisCombinatorial chemistryOrganic chemistryCatalysisPhysical chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Catalytic Reactions