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Large yet flexible N-heterocyclic carbene ligands for palladium catalysis

(2013) CHEMISTRY-A EUROPEAN JOURNAL. 19(51). p.17358-17368
Author
Organization
Abstract
A straightforward and scalable eight-step synthesis of new N-heterocyclic carbenes (NHCs) has been developed from inexpensive and readily available 2-nitro-m-xylene. This process allows for the preparation of a novel class of NHCs coined ITent (Tent for tentacular) of which the well-known IMes (N,N-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene), IPr (N,N-bis(2,6-di(2-propyl)phenyl)imidazol-2-ylidene) and IPent (N,N-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene) NHCs are the simplest and already known congeners. The synthetic route was successfully used for the preparation of three members of the ITent family: IPent (N,N-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene), IHept (N,N-bis(2,6-di(4-heptyl)phenyl)imidazol-2-ylidene) and INon (N,N-bis(2,6-di(5-nonyl)phenyl)imidazol-2-ylidene). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes. Finally the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated.
Keywords
bulky, catalysis, flexible, N-heterocyclic carbene, palladium, tentacular, CROSS-COUPLING REACTIONS, ORTHO-SUBSTITUTED BIARYLS, SUZUKI-MIYAURA COUPLINGS, PD-PEPPSI-IPENT, ARYL CHLORIDES, ROOM-TEMPERATURE, AMINATION REACTIONS, BUCHWALD-HARTWIG, BOND FORMATION, C-N

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MLA
Meiries, Sebastien, et al. “Large yet Flexible N-Heterocyclic Carbene Ligands for Palladium Catalysis.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 19, no. 51, 2013, pp. 17358–68.
APA
Meiries, S., Le Duc, G., Chartoire, A., Collado, A., Speck, K., Arachchige, K. S. A., … Nolan, S. (2013). Large yet flexible N-heterocyclic carbene ligands for palladium catalysis. CHEMISTRY-A EUROPEAN JOURNAL, 19(51), 17358–17368.
Chicago author-date
Meiries, Sebastien, Gaetan Le Duc, Anthony Chartoire, Alba Collado, Klaus Speck, Kasun S Athukorala Arachchige, Alexandra MZ Slawin, and Steven Nolan. 2013. “Large yet Flexible N-Heterocyclic Carbene Ligands for Palladium Catalysis.” CHEMISTRY-A EUROPEAN JOURNAL 19 (51): 17358–68.
Chicago author-date (all authors)
Meiries, Sebastien, Gaetan Le Duc, Anthony Chartoire, Alba Collado, Klaus Speck, Kasun S Athukorala Arachchige, Alexandra MZ Slawin, and Steven Nolan. 2013. “Large yet Flexible N-Heterocyclic Carbene Ligands for Palladium Catalysis.” CHEMISTRY-A EUROPEAN JOURNAL 19 (51): 17358–17368.
Vancouver
1.
Meiries S, Le Duc G, Chartoire A, Collado A, Speck K, Arachchige KSA, et al. Large yet flexible N-heterocyclic carbene ligands for palladium catalysis. CHEMISTRY-A EUROPEAN JOURNAL. 2013;19(51):17358–68.
IEEE
[1]
S. Meiries et al., “Large yet flexible N-heterocyclic carbene ligands for palladium catalysis,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 19, no. 51, pp. 17358–17368, 2013.
@article{8168613,
  abstract     = {A straightforward and scalable eight-step synthesis of new N-heterocyclic carbenes (NHCs) has been developed from inexpensive and readily available 2-nitro-m-xylene. This process allows for the preparation of a novel class of NHCs coined ITent (Tent for tentacular) of which the well-known IMes (N,N-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene), IPr (N,N-bis(2,6-di(2-propyl)phenyl)imidazol-2-ylidene) and IPent (N,N-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene) NHCs are the simplest and already known congeners. The synthetic route was successfully used for the preparation of three members of the ITent family: IPent (N,N-bis(2,6-di(3-pentyl)phenyl)imidazol-2-ylidene), IHept (N,N-bis(2,6-di(4-heptyl)phenyl)imidazol-2-ylidene) and INon (N,N-bis(2,6-di(5-nonyl)phenyl)imidazol-2-ylidene). The electronic and steric properties of each NHC were studied through the preparation of both nickel and palladium complexes. Finally the effect of these new ITent ligands in Pd-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-couplings was investigated.},
  author       = {Meiries, Sebastien and Le Duc, Gaetan and Chartoire, Anthony and Collado, Alba and Speck, Klaus and Arachchige, Kasun S Athukorala and Slawin, Alexandra MZ and Nolan, Steven},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {bulky,catalysis,flexible,N-heterocyclic carbene,palladium,tentacular,CROSS-COUPLING REACTIONS,ORTHO-SUBSTITUTED BIARYLS,SUZUKI-MIYAURA COUPLINGS,PD-PEPPSI-IPENT,ARYL CHLORIDES,ROOM-TEMPERATURE,AMINATION REACTIONS,BUCHWALD-HARTWIG,BOND FORMATION,C-N},
  language     = {eng},
  number       = {51},
  pages        = {17358--17368},
  title        = {Large yet flexible N-heterocyclic carbene ligands for palladium catalysis},
  url          = {http://dx.doi.org/10.1002/chem.201302471},
  volume       = {19},
  year         = {2013},
}

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