Site‐Selective C−H Functionalization of Carbazoles
Mazen Elsaid, Robbie Ge, Chong Liu, Debabrata Maiti, Haibo Ge
Abstract
Carbazole alkaloids hold great potential in pharmaceutical and material sciences. However, the current approaches for C1 functionalization of carbazoles rely on the use of a pre-installed directing group, severely limiting their applicability and hindering their overall efficiency. Herein, we report for the first time the development of direct Pd-catalyzed C-H alkylation and acylation of carbazoles assisted by norbornene (NBE) as a transient directing mediator. Notably, the involvement of a six-membered palladacycle intermediate was suggested in this case, representing the first example of such intermediacy within the extensively studied Pd/norbornene reactions realm.
Topics & Concepts
CarbazoleSurface modificationNorborneneAlkylationChemistryAcylationCombinatorial chemistryStereocenterHomogeneousStereochemistryCatalysisOrganic chemistryEnantioselective synthesisPolymerThermodynamicsPhysicsPhysical chemistryMonomerCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCatalytic Alkyne Reactions