Well-defined N-heterocyclic carbenes-palladium(II) precatalysts for cross-coupling reactions

Accounts of Chemical Research

Volumn 41, Issue 11, 2008, Pages 1440-1449

  Marion, Nicolas ^a   Nolan, Steven P ^a  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 57549115030     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800020y     Document Type: Review

References (88)

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39. 2 complex (NHC = N-heterocyclic carbene). Chem. Commun., 2008, 3190-3192.
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46. Bedford, R. B.; Betham, M.; Coles, S. J.; Frost, R. M.; Hursthouse, M. B. An Evaluation of Phosphine and Carbene Adducts of Phosphite- and Phosphinite-Based Palladacycles in the Coupling of Alkyl Bromides With Aryl Boronic Acids. Tetrahedron 2005, 61, 9663-9669.
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48. Viciu, M. S.; Kelly, R. A., III; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Synthesis, Characterization, and Catalytic Activity of N-Heterocyclic Carbene (NHC) Palladacycle Complexes. Org. Lett. 2003, 5, 1479-1482.
49. Navarro, O.; Marion, N.; Oonishi, Y.; Kelly, R. A., III; Nolan, S. P. Suzuki-Miyaura, α-Ketone Arylation and Dehalogenation Reactions by a Versatile N-Heterocyclic Carbene-Palladacycle Complex. J. Org. Chem. 2006, 71, 685-692.
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51. Navarro, O.; Kelly, R. A., III; Nolan, S. P. A General Method for the Suzuki-Miyaura Cross-Coupling of Sterically Hindered Aryl Chlorides: Synthesis of Di- and Tri-ortho- Substituted Biaryls in 2-Propanol at Room Temperature. J. Am. Chem. Soc. 2003, 125, 16194-16195.
52. Tetra-ortho-substituted biaryls are still one of the greatest challenges of the Suzuki-Miyaura reaction; for rare catalytic systems enabling their formation, see: (a) Walker, S. D.; Barder, T, E.; Martinelli, J. R.; Buchwald, S. L. A Rationally Designed Universal Catalyst for Suzuki-Miyaura Coupling Processes. Angew. Chem., Int. Ed. 2004, 43, 1871-1876. (b) See also ref 16c.
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55. Singh, R.; Viciu, M. S.; Kramareva, N.; Navarro, O.; Nolan, S. P. Simple (Imidazol-2-ylidene)-Pd-Acetate Complexes as Effective Pre-catalysts for Sterically Hindered Suzuki-Miyaura Couplings. Org. Lett. 2005, 7, 1829-1832.
56. Singh, R.; Nolan, S. P. An Efficient and Mild Protocol for the α-Arylation of Ketones Mediated by an (Imidazol-2-ylidene) palladium(acetate) System. J. Organomet. Chem. 2005, 690, 5832-5840.
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59. Navarro, O.; Marion, N.; Scott, N. M.; González, J.; Amoroso, D.; Bell, A.; Nolan, S. P. Synthesis of Novel (NHC)Pd(acac)Cl Complexes (acac = acetylacetonate) and Their Activity in Cross-Coupling Reactions. Tetrahedron 2005, 61, 9716-9722.
60. Marion, N.; de Frémont, P.; Puijk, I. M.; Ecarnot, E. C.; Amoroso, D.; Bell, A.; Nolan, S. P. N-Heterocyclic Carbene-Palladium Complexes [(NHC)Pd(acac)Cl]: Improved Synthesis and Catalytic Activity in Large-Scale Cross-Coupling Reactions. Adv. Synth. Catal. 2007, 349, 2380-2384.
61. Marion, N.; Ecarnot, E. C.; Navarro, O.; Amoroso, D.; Bell, A.; Nolan, S. P. (IPr)Pd(acac)Cl: An Easily Synthesized, Efficient, and Versatile Precatalyst for C-N and C-C Bond Formation. J. Org. Chem. 2006, 71, 3816-3821.
62. Marion, N.; Eelman, M. D.; Fogg, D. E.; Nolan, S. P. Unpublished results.
63. Viciu, M. S.; Navarro, O.; Germaneau, R. F.; Kelly, R. A., III; Sommer, W.; Marion, N.; Stevens, E. D.; Cavallo, L.; Nolan, S. P. Synthetic and Structural Studies of (NHC)Pd(allyl)Cl Complexes (NHC = N-Heterocyclic Carbene). Organometallics 2004, 23, 1629-1635.
64. (a) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Well-Defined, Air-Stable (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Catalysts for the Arylation of Ketones. Org. Lett. 2002, 4, 4053-4056.
65. (b) Viciu, M. S.; Germaneau, R. F.; Navarro-Fernandez, O.; Stevens, E. D.; Nolan, S. P. Activity and Reactivity of (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes in Cross-Coupling Reactions. Organometallics 2002, 21, 5470-5472.
66. (a) Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. Cross-Coupling and Dehalogenation Reactions Catalyzed by (N-Heterocyclic Carbene)Pd(allyl)Cl Complexes. J. Org. Chem. 2004, 64, 3173-3180.
67. (b) Marion, N.; Navarro, O.; Kelly, R. A., III; Nolan, S. P. Synthesis of Biaryl, Arylamine and Aryl Ketone Compounds Using a Commercially Available Air- and Moisture-Stable Palladium Catalyst. Synthesis 2003, 2590-2592.
68. Compounds 31, 32 and 41 are commercially available from Strem Chemicals and from Umicore AG.
69. Navarro, O.; Nolan, S. P. Large-Scale One-Pot Synthesis of N-Heterocyclic Carbene-Pd(allyl)Cl Complexes. Synthesis 2006, 366-367.
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72. For key references, see: (a) Reference 33.
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75. Navarro, O.; Marion, N.; Mei, J.; Nolan, S. P. Rapid Room Temperature Buchwald-Hartwig and Suzuki - Miyaura Couplings of Heteroaromatic Compounds Employing Low Catalyst Loadings. Chem. - Eur. J. 2006, 12, 5142-5148.
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85. For rare reports dealing with mechanistic studies on monodentate NHC-Pd systems in cross-coupling, see: (a) Albert, K.; Gisdakis, P.; Rösch, N. On C-C Coupling by Carbene-Stabilized Palladium Catalysts: A Density Functional Study on the Heck Reaction. Organometallics 1998, 77, 1608-1616.
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