A four-component reaction to access 3,3-disubstituted indolines <i>via</i> the palladium–norbornene-catalyzed <i>ortho</i> amination/<i>ipso</i> conjunctive coupling
Alexander J. Rago, Rong Ye, Xin Liu, Guangbin Dong
Abstract
conjunctive coupling using an alkene and an external nucleophile. The use of alkene-tethered nitrogen electrophiles provides a rapid and modular synthesis of 3,3-disubstituted indolines from readily available aryl iodides. The reaction exhibits broad functional group tolerance, and its utility is exemplified in a streamlined formal synthesis of a rhodamine dye. Preliminary results of the asymmetric version of this reaction have also been obtained.
Topics & Concepts
NorborneneAlkeneChemistryNucleophileArylAminationElectrophilePalladiumCatalysisCombinatorial chemistryCoupling reactionMedicinal chemistryPhotochemistryOrganic chemistryPolymerAlkylMonomerCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsSynthesis and Catalytic Reactions