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

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 reac...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 139; no. 30; pp. 10228 - 10231
Main Authors Walker, James A, Vickerman, Kevin L, Humke, Jenna N, Stanley, Levi M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.08.2017
Amer Chemical Soc
Subjects
amides
catalysts
chemical bonding
Chemistry
Chemistry, Multidisciplinary
esters
nickel
Physical Sciences
Science & Technology
BENZOCYCLOBUTENONES
KETONE SYNTHESIS
NICKEL CATALYSIS
ARYL ESTERS
HETEROCYCLIC CARBENE COMPLEXES
TWISTED AMIDES
OLEFINS
CLEAVAGE
QUATERNARY CENTERS
GENERAL-METHOD
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Summary: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.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.7b06191