One-Pot Synthesis of Pyrrolo[1,2-f]phenanthridines From 1-Arylpyrroles via Successive Palladium-Catalyzed Direct Arylations - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2021

One-Pot Synthesis of Pyrrolo[1,2-f]phenanthridines From 1-Arylpyrroles via Successive Palladium-Catalyzed Direct Arylations

Résumé

A Pd-catalyzed annulative pi-extension reaction of 1-arylpyrroles using 1,2-dihalobenzenes as the coupling partners was investigated. The higher reactivity of pyrrole C2-H bond compared to C-H bonds of the aryl unit of 1-arylpyrroles allows selective synthesis of pyrrolo[1,2-f]phenanthridines via successive palladium-catalyzed direct intermolecular followed by intramolecular direct arylation steps. From 1-bromo-2-iodobenzenes bearing substituents at C4- or C5-positions and ortho-, meta- or para-substituted 1-arylpyrroles, the access to pyrrolo[1,2-f]phenanthridines containing substituents at C5, C6, C7, C8, C10 and/or C11 positions is possible.
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Dates et versions

hal-03414079 , version 1 (10-11-2021)

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Paternité - Pas d'utilisation commerciale

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Citer

Jian Zhang, Xinzhe Shi, Henri Doucet. One-Pot Synthesis of Pyrrolo[1,2-f]phenanthridines From 1-Arylpyrroles via Successive Palladium-Catalyzed Direct Arylations. European Journal of Organic Chemistry, 2021, 2021 (35), pp.4974-4983. ⟨10.1002/ejoc.202100766⟩. ⟨hal-03414079⟩
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