Synfacts 2009(3): 0261-0261  
DOI: 10.1055/s-0028-1087799
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Isoquinolin-1-ones via Pd-Catalyzed Carbonylation-Heteroannulation

Contributor(s): Victor Snieckus, Jignesh J. Patel
Z. Zheng, H. Alper*
University of Ottawa, Canada
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Publikationsverlauf

Publikationsdatum:
19. Februar 2009 (online)

Significance

A palladium-catalyzed carbonylative cyclization of imines derived from diethyl (2-­iodoaryl)malonates and imidoyl chlorides provides a synthesis of substituted isoquinolin-1(2H)-ones in good yields. As shown, a mechanism involving a palladium-catalyzed carbonylation followed by decarboxylation process is proposed. The reactions depend significantly on the choice of ligand used: bidentate phosphines gave trace amounts of product, while trialkylphosphines gave complex mixtures. The optimum conditions involve use of bulky aryl phosphines with Pd(OAc)2 and 400 psi pressure of CO at 120 ˚C in tetrahydrofuran which may therefore limit the process for large-scale synthesis.