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

Jonathan Hédouin (1) , Cédric Schneider (1) , I. Gillaizeau (2) , Christophe Hoarau (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 ICOA - Institut de Chimie Organique et Analytique

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.

Domaines: Chimie

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, 2018, 20 (19), pp.6027-6032. ⟨10.1021/acs.orglett.8b02365⟩. ⟨hal-02024502⟩