Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 30, Pages 10228-10231Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b06191
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Funding
- NSF [CHE-1352080]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1352080] Funding Source: National Science Foundation
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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-benzy-12,3-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.
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