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Article: Catalytic annulation of heterocycles via a novel redox process involving the imidazolium salt N-heterocyclic carbene couple
Title | Catalytic annulation of heterocycles via a novel redox process involving the imidazolium salt N-heterocyclic carbene couple |
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Authors | |
Issue Date | 2008 |
Citation | Organometallics, 2008, v. 27, n. 13, p. 3153-3160 How to Cite? |
Abstract | A 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 Identifier | http://hdl.handle.net/10722/219583 |
ISSN | 2023 Impact Factor: 2.5 2023 SCImago Journal Rankings: 0.654 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Normand, Adrien T. | - |
dc.contributor.author | Yen, Swee Kuan | - |
dc.contributor.author | Huynh, Han Vinh | - |
dc.contributor.author | Hor, T. S Andy | - |
dc.contributor.author | Cavell, Kingsley J. | - |
dc.date.accessioned | 2015-09-23T02:57:27Z | - |
dc.date.available | 2015-09-23T02:57:27Z | - |
dc.date.issued | 2008 | - |
dc.identifier.citation | Organometallics, 2008, v. 27, n. 13, p. 3153-3160 | - |
dc.identifier.issn | 0276-7333 | - |
dc.identifier.uri | http://hdl.handle.net/10722/219583 | - |
dc.description.abstract | A 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.language | eng | - |
dc.relation.ispartof | Organometallics | - |
dc.title | Catalytic annulation of heterocycles via a novel redox process involving the imidazolium salt N-heterocyclic carbene couple | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/om800140n | - |
dc.identifier.scopus | eid_2-s2.0-47949114467 | - |
dc.identifier.volume | 27 | - |
dc.identifier.issue | 13 | - |
dc.identifier.spage | 3153 | - |
dc.identifier.epage | 3160 | - |
dc.identifier.isi | WOS:000257448500037 | - |
dc.identifier.issnl | 0276-7333 | - |