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Article: Catalytic annulation of heterocycles via a novel redox process involving the imidazolium salt N-heterocyclic carbene couple

TitleCatalytic annulation of heterocycles via a novel redox process involving the imidazolium salt N-heterocyclic carbene couple
Authors
Issue Date2008
Citation
Organometallics, 2008, v. 27, n. 13, p. 3153-3160 How to Cite?
AbstractA novel atom-efficient catalytic reaction, which converts imidazolium salts, with N-butenyl, N-substituted butenyl, and N-pentenyl substituents, into five- and six-membered fused-ring imidazolium and thiazolium salts has been developed. The reaction proceeds through azolium, C2-H, oxidative addition to Ni(O) followed by intramolecular insertion of the N-alkenyl double bond into the Ni hydride to give an intramolecularly bound carbene-Ni-alkyl intermediate. Reductive elimination of the linked carbene and alkyl groups gives the fused-ring azolium products and regenerates the Ni(0) catalyst. Products are potential building blocks for the synthesis of pharmaceuticals and novel ionic liquids. For example, 1,7-dimethyl-6,7-dihydro-5H-pyrrole[l,2-α] imidazolium bromide (2f), a five-membered fused-ring imidazolium salt, is formed from the catalytic ring closing of l-butenyl-3-methylimidazolium bromide (1f). The reaction proceeds at moderate temperatures (50 °C) to give the products in high yield and selectivity. The catalyst was formed in situ from Ni(COD) 2 plus added ligand L (where L = IMes, SMes, IPr, SPr, 4,5-Me 2IPr, PPh3, PCy3, PCy2(Biphenyl), P'Bu3) in DMF. © 2008 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/219583
ISSN
2015 Impact Factor: 4.186
2015 SCImago Journal Rankings: 2.043

 

DC FieldValueLanguage
dc.contributor.authorNormand, Adrien T.-
dc.contributor.authorYen, Swee Kuan-
dc.contributor.authorHuynh, Han Vinh-
dc.contributor.authorHor, T. S Andy-
dc.contributor.authorCavell, Kingsley J.-
dc.date.accessioned2015-09-23T02:57:27Z-
dc.date.available2015-09-23T02:57:27Z-
dc.date.issued2008-
dc.identifier.citationOrganometallics, 2008, v. 27, n. 13, p. 3153-3160-
dc.identifier.issn0276-7333-
dc.identifier.urihttp://hdl.handle.net/10722/219583-
dc.description.abstractA novel atom-efficient catalytic reaction, which converts imidazolium salts, with N-butenyl, N-substituted butenyl, and N-pentenyl substituents, into five- and six-membered fused-ring imidazolium and thiazolium salts has been developed. The reaction proceeds through azolium, C2-H, oxidative addition to Ni(O) followed by intramolecular insertion of the N-alkenyl double bond into the Ni hydride to give an intramolecularly bound carbene-Ni-alkyl intermediate. Reductive elimination of the linked carbene and alkyl groups gives the fused-ring azolium products and regenerates the Ni(0) catalyst. Products are potential building blocks for the synthesis of pharmaceuticals and novel ionic liquids. For example, 1,7-dimethyl-6,7-dihydro-5H-pyrrole[l,2-α] imidazolium bromide (2f), a five-membered fused-ring imidazolium salt, is formed from the catalytic ring closing of l-butenyl-3-methylimidazolium bromide (1f). The reaction proceeds at moderate temperatures (50 °C) to give the products in high yield and selectivity. The catalyst was formed in situ from Ni(COD) 2 plus added ligand L (where L = IMes, SMes, IPr, SPr, 4,5-Me 2IPr, PPh3, PCy3, PCy2(Biphenyl), P'Bu3) in DMF. © 2008 American Chemical Society.-
dc.languageeng-
dc.relation.ispartofOrganometallics-
dc.titleCatalytic annulation of heterocycles via a novel redox process involving the imidazolium salt N-heterocyclic carbene couple-
dc.typeArticle-
dc.description.natureLink_to_subscribed_fulltext-
dc.identifier.doi10.1021/om800140n-
dc.identifier.scopuseid_2-s2.0-47949114467-
dc.identifier.volume27-
dc.identifier.issue13-
dc.identifier.spage3153-
dc.identifier.epage3160-

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