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Pd-Catalyzed Aminocarbonylation of the Blaise Reaction Intermediate: One-Pot Synthesis of (Z)-3-Methyleneisoindolin-1-ones from Nitriles

Zi Xuan, Da Jung Jung, Hyun Ji Jeon and Sang-gi Lee*

*Department of Chemistry and Nano Science, Ewha Womans University, 120-750 Seoul, Korea, Email: sanggiewha.ac.kr

Z. Xuan, D. J. Jung, H. J. Jeon, S.-g. Lee, J. Org. Chem., 2016, 81, 10094-10098.

DOI: 10.1021/acs.joc.6b02095 (free Supporting Information)


Abstract

A tandem sequential reaction 2-bromoarylnitriles with a Reformatsky reagent (Blaise reaction), followed by Pd-catalyzed intramolecular aminocarbonylation with carbon monoxide at 1 atm pressure provides (Z)-3-methyleneisoindolin-1-ones. The conformational flexibility of the bisphophine ligand is of great importance to the success of this tandem aminocarbonylation reaction.

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Key Words

Blaise Reaction, Isoindolinones


ID: J42-Y2016