American Chemical Society
ja7b06191_si_001.pdf (22.02 MB)

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

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journal contribution
posted on 2017-07-14, 00:00 authored by James A. Walker, Kevin L. Vickerman, Jenna N. Humke, Levi M. Stanley
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.