Highly selective biaryl cross-coupling reactions between aryl halides and aryl Grignard reagents: A new catalyst combination of N-heterocyclic carbenes and iron, cobalt, and nickel fluorides

Journal of the American Chemical Society

Volumn 131, Issue 33, 2009, Pages 11949-11963

  Hatakeyama, Takuji ^a   Hashimoto, Sigma ^a,b   Ishizuka, Kentaro ^a,b   Nakamura, Masaharu ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDES; ARYL CHLORIDE; ARYL HALIDES; BIARYLS; CATALYTIC CYCLES; CATALYTIC EFFECTS; CONTROL EXPERIMENTS; COUNTERIONS; CROSS COUPLING REACTIONS; CROSS-COUPLING PRODUCTS; CROSS-COUPLINGS; DFT CALCULATION; EXISTING METHOD; GRIGNARD REAGENT; HETEROLEPTIC; HIGH SELECTIVITY; HIGH YIELD; HOMOCOUPLING; IRON CATALYST; IRON FLUORIDES; IRON-GROUP METAL; METAL CHLORIDES; METAL FLUORIDE; METAL-CATALYZED CROSS-COUPLING REACTIONS; N-HETEROCYCLIC CARBENES; NHC LIGANDS; NICKEL FLUORIDE; OXIDATIVE ADDITIONS; PALLADIUM CATALYST; PHOSPHINE LIGANDS; PRACTICAL METHOD; REACTIVE INTERMEDIATE; THEORETICAL STUDY; TRANSMETALATION; UNSYMMETRICAL;

ARGON; BROMINE COMPOUNDS; CATALYSIS; CATALYST SELECTIVITY; CHELATION; CHEMICAL BONDS; CHEMICAL REACTIVITY; CHLORINE COMPOUNDS; COBALT; FLUORINE COMPOUNDS; LIGANDS; LITHIUM BATTERIES; METALS; NICKEL; NICKEL ALLOYS; OPTICAL COMMUNICATION; PALLADIUM; PHOSPHORUS COMPOUNDS; STEEL BEAMS AND GIRDERS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

COMPLEXATION;

BROMIDE; CARBENOID; CHLORIDE; COBALT; FLUORIDE; GRIGNARD REAGENT; HALIDE; HETEROCYCLIC COMPOUND; IODIDE; IRON; MAGNESIUM DERIVATIVE; NICKEL; PALLADIUM; PHOSPHINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; OXIDATION; STOICHIOMETRY; SYNTHESIS;

CATALYSIS; COBALT; FERRIC COMPOUNDS; FLUORIDES; HALOGENS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, AROMATIC; INDICATORS AND REAGENTS; NICKEL;

EID: 69049084551     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9039289     Document Type: Article

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181. Noda, D.; Sunada, Y.; Hatakeyama, T.; Nakamura, M.; Nagashima, H. J. Am. Chem. Soc. 2009, 131, 6078-6079.
182. Although the canonical mechanism has been widely accepted for Pdcatalyzed cross-coupling reactions, several alternatives have been proposed for the cross-coupling reactions based on the first-row transition metal catalysts including Fe, Co, and Ni. See refs 14f, 15o, 26c, 42, and 43.
183. (a) Nakamura, E.; Mori, S.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 8273-8274.
184. (b) Mori, S.; Nakamura, E.; Morokuma, K. J. Am. Chem. Soc. 2000, 122, 7294-7307.
185. 2:
186. (b) Fürstner, A.; Krause, H.; Lehmann, C. W. Angew. Chem., Int. Ed. 2006, 45, 440-444. Fe-F complex:
187. (c) Vela, J.; Smith, J. M.; Yu, Y.; Ketterer, N. A.; Flaschenriem, C. J.; Lachicotte, R. J.; Holland, P. L. J. Am. Chem. Soc. 2005, 127, 7857-7870.
188. The DFT calculations were performed using the B3LYP hybrid functional and the 6-31G* basis set. All stationary points were optimized without any symmetry assumptions, and characterized all by normal coordinate analysis at the same level of the geometry optimization. Details are described in the Supporting Information. Theoretical studies using DFT method on (0)-(II) mechanism for nickel-catalyzed cross-coupling and related reactions: Reinhold, M.; McGrady, J. E.; Perutz, R. N. J. Am. Chem. Soc. 2004, 126, 5268-5267, and references cited therein.
189. See also a recent paper: Yoshikai, N.; Matsuda, H.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 15258-15259.
190. Molecular structures and all electron energies of the stationary points are described in the Supporting Information.
191. 2. Details are described in the Supporting Information.
192. Because the B3LYP functional have been known to overestimate the stability of high spin states, we examined several functionals including the one without HF exchange term (BP91) and the other with modified admixture of HF term (B3LYP*) to obtain the virtually same results. Further computational study on the present catalytic cross-coupling reactions waits for the development of multiconfigurational treatment such as CASSCF calculation using realistic chemical models, and of course, it has been so far impractical. Zein, S.; Borshch, S. A.; Fleurat-Lessard, P.; Casida, M. E.; Chermette, H. J. Chem. Phys. 2007, 126, 014105.
193. For B3LYP* and the coefficient of exact exchange admixture in DFT calculation affects relative energies of states of different multiplicity; see: Reiher, M.; Salomon, O.; Hess, B. A. Theor. Chem. Acc. 2001, 107, 48-55.
194. No reaction pathway for oxidative addition process was obtained in singlet state.