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

James A. Walker Jr., Kevin L. Vickerman, Jenna N. Humke and Levi M. Stanley*

*Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States, Email: lstanleyiastate.edu

J. A. Walker Jr., K. L. Vickerman, J. N. Humke, L. M. Stanley, J. Am. Chem. Soc., 2017, 139, 10228-10231.

DOI: 10.1021/jacs.7b06191 (free Supporting Information)


Abstract

A Ni-catalyzed formal exo-selective carboacylation of o-allylbenzamides with arylboronic acid pinacol esters provides 2-benzyl-2,3-dihydro-1H-inden-1-ones in good yields. 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.

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proposed mechanism



Key Words

indanones


ID: J48-Y2017