Site-Selective C-H Functionalization of Carbazoles.

Mazen Elsaid, Robbie Ge, Chong Liu, Debabrata Maiti, Haibo Ge

Angewandte Chemie (International ed. in English) 2023 Jun 19

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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. © 2023 Wiley-VCH GmbH.

Citation

Mazen Elsaid, Robbie Ge, Chong Liu, Debabrata Maiti, Haibo Ge. Site-Selective C-H Functionalization of Carbazoles. Angewandte Chemie (International ed. in English). 2023 Jun 19;62(25):e202303110