Double C-H bond functionalization for the annulative pi-extension of 1-arylimidazoles: A palladium-catalyzed one pot access to imidazo[1,5-f]phenanthridines - INSTITUT DES SCIENCES CHIMIQUES DE RENNES Accéder directement au contenu
Article Dans Une Revue Applied Organometallic Chemistry Année : 2022

Double C-H bond functionalization for the annulative pi-extension of 1-arylimidazoles: A palladium-catalyzed one pot access to imidazo[1,5-f]phenanthridines

Résumé

The Pd-catalyzed annulative pi-extension reaction of 1-arylimidazoles for the one pot preparation of imidazo[1,5-f]phenanthridines was explored. The higher reactivity of imidazole C5-H bond compared to C2-H bond of imidazoles for Pd-catalyzed direct arylation in the presence of carboxylate bases allows the selective synthesis of imidazo[1,5-f]phenanthridines. The reaction proceeds via successive palladium-catalyzed direct intermolecular C5-arylation of the imidazole unit followed by an intramolecular direct arylation step. This synthetic pathway allowed us to describe the first synthesis of imidazo[1,5-f]phenanthridine. Moreover, by using the appropriate substrates, the introduction of desired functional groups at positions 5, 7, 10, and 11 of imidazo[1,5-f]phenanthridines is possible.
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Dates et versions

hal-03714973 , version 1 (27-09-2022)

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Linhao Liu, Hai-Yun Huang, Henri Doucet. Double C-H bond functionalization for the annulative pi-extension of 1-arylimidazoles: A palladium-catalyzed one pot access to imidazo[1,5-f]phenanthridines. Applied Organometallic Chemistry, 2022, 36 (7), pp.-e6747. ⟨10.1002/aoc.6747⟩. ⟨hal-03714973⟩
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