Site-Selective C−H Functionalization of Carbazoles


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.


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C(sp2)-H Functionalization, Carbazole, Norbornene, Palladium, Transient Directing Mediator


Elsaid, M., Ge, R., Liu, C., Maiti, D., Ge, H., Angew. Chem. Int. Ed. 2023, 62, e202303110.