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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| Published in | Journal of the American Chemical Society Vol. 139; no. 30; pp. 10228 - 10231 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
02.08.2017
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | 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. 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.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. 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. 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. |
| Author | Walker, James A Humke, Jenna N Vickerman, Kevin L Stanley, Levi M |
| AuthorAffiliation | Department of Chemistry Iowa State University |
| AuthorAffiliation_xml | – name: Iowa State University – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: James A surname: Walker fullname: Walker, James A – sequence: 2 givenname: Kevin L surname: Vickerman fullname: Vickerman, Kevin L – sequence: 3 givenname: Jenna N surname: Humke fullname: Humke, Jenna N – sequence: 4 givenname: Levi M orcidid: 0000-0001-8804-1146 surname: Stanley fullname: Stanley, Levi M email: lstanley@iastate.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28708388$$D View this record in MEDLINE/PubMed |
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| Keywords | BENZOCYCLOBUTENONES KETONE SYNTHESIS NICKEL CATALYSIS ARYL ESTERS HETEROCYCLIC CARBENE COMPLEXES TWISTED AMIDES OLEFINS CLEAVAGE QUATERNARY CENTERS GENERAL-METHOD |
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| Snippet | We report Ni-catalyzed formal carboacylation of o-allylbenzamides with arylboronic acid pinacol esters. The reaction is triggered by oxidative addition of an... |
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| SubjectTerms | amides catalysts chemical bonding Chemistry Chemistry, Multidisciplinary esters nickel Physical Sciences Science & Technology |
| Title | Ni-Catalyzed Alkene Carboacylation via Amide C–N Bond Activation |
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