5 years ago

Ni-Catalyzed Alkene Carboacylation via Amide C–N Bond Activation

Ni-Catalyzed Alkene Carboacylation via Amide C–N Bond Activation
Jenna N. Humke, James A. Walker, Levi M. Stanley, Kevin L. Vickerman
We report Ni-catalyzed formal carboacylation of o-allylbenzamides with arylboronic acid pinacol esters. The reaction is triggered by oxidative addition of an activated amide C–N bond to a Ni(0) catalyst and proceeds via alkene insertion into a Ni(II)–acyl bond. The exo-selective carboacylation reaction generates 2-benzyl-2,3-dihydro-1H-inden-1-ones in moderate to high yields (46–99%) from a variety of arylboronic acid pinacol esters and substituted o-allylbenzamides. These results show that amides are practical substrates for alkene carboacylation via amide C–N bond activation, and this approach bypasses challenges associated with alkene carboacylation triggered by C–C bond activation.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b06191

DOI: 10.1021/jacs.7b06191

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