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Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues

Abstract : Palladium-catalyzed intramolecular carbopalladation onto allenamides completed by direct C–H allylation of heterocycles is studied. The domino construction/heteroarylation of isoquinolone process is first achieved. A general three-step one-pot strategy, involving in situ generation of allenamide, π-allyl-Pd complex generation, and interception with heteroarenes, has been subsequently set up. This methodology has been extended to the construction/heteroarylation of indoles, dihydroquinolines, isoquinolin(on)es, and medium-sized nitrogen heterocycles, which are known to be key challenging structural motifs with pharmaceutical significance.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02024502
Contributor : Madeleine Roux-Merlin <>
Submitted on : Tuesday, February 19, 2019 - 11:09:46 AM
Last modification on : Thursday, July 2, 2020 - 3:28:44 AM

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Jonathan Hédouin, Cédric Schneider, I. Gillaizeau, Christophe Hoarau. Palladium-Catalyzed Domino Allenamide Carbopalladation/Direct C-H Allylation of Heteroarenes: Synthesis of Primprinine and Papaverine Analogues. Organic Letters, American Chemical Society, 2018, 20 (19), pp.6027-6032. ⟨10.1021/acs.orglett.8b02365⟩. ⟨hal-02024502⟩

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