Atom Transfer Radical Addition Reactions of Quinoxalin-2(1<i>H</i>)-ones with CBr<sub>4</sub> and Styrenes Using Mes-Acr-MeClO<sub>4</sub> Photocatalyst
Buddhadeb Pal, Sathi Sahoo, Prasenjit Mal
Abstract
The atom transfer radical addition (ATRA) reaction is defined as a method for introducing halogenated compounds into alkenes via a radical mechanism. In this study, we present an ATRA approach for achieving regioselective functionalization of quinoxalin-2(1 H )-ones by activating C–Br bonds of CBr 4 and subsequent trihaloalkyl-carbofunctionalization of styrenes employing the 9-mesityl-10-methylacridinium perchlorate (Fukuzumi) photocatalyst under 3W blue LED (450–470 nm) irradiation. This three-component radical cascade process demonstrates remarkable efficiency in the synthesis of 1-methyl-3-(3,3,3-tribromo-1-(4-chlorophenyl)propyl)quinoxalin-2(1 H )-one derivatives.
Topics & Concepts
ChemistryRegioselectivityPhotocatalysisSurface modificationRadical ionMedicinal chemistryPerchloratePhotochemistryCombinatorial chemistryOrganic chemistryCatalysisPhysical chemistryIonRadical Photochemical ReactionsOxidative Organic Chemistry ReactionsFluorine in Organic Chemistry