Catalyst complex with carbene ligand

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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C548S103000, C556S021000, C556S136000, C556S137000, C502S152000, C502S162000, C585S350000, C585S366000, C585S643000

Reexamination Certificate

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07622590

ABSTRACT:
Catalytic complexes including a metal atom having anionic ligands, at least one nucleophilic carbene ligand, and an alkylidene, vinylidene, or allenylidene ligand. The complexes are highly stable to air, moisture and thermal degradation. The complexes are designed to efficiently carry out a variety of olefin metathesis reactions.

REFERENCES:
patent: 4681956 (1987-07-01), Schrock
patent: 5077414 (1991-12-01), Arduengo, III
patent: 5146033 (1992-09-01), Schrock et al.
patent: 5182405 (1993-01-01), Arduengo, III
patent: 5312940 (1994-05-01), Grubbs et al.
patent: 5342909 (1994-08-01), Grubbs et al.
patent: 5710298 (1998-01-01), Grubbs et al.
patent: 5728785 (1998-03-01), Grubbs et al.
patent: 5728839 (1998-03-01), Herrmann et al.
patent: 5728917 (1998-03-01), Grubbs et al.
patent: 5750815 (1998-05-01), Grubbs et al.
patent: 5831108 (1998-11-01), Grubbs et al.
patent: 5917071 (1999-06-01), Grubbs et al.
patent: 5932664 (1999-08-01), Chen et al.
patent: 5969170 (1999-10-01), Grubbs et al.
patent: 5977393 (1999-11-01), Grubbs et al.
patent: 6025496 (2000-02-01), Herrmann et al.
patent: 6048993 (2000-04-01), Grubbs et al.
patent: 6077805 (2000-06-01), Van Der Schaaf et al.
patent: 6107420 (2000-08-01), Grubbs et al.
patent: 6111121 (2000-08-01), Grubbs et al.
patent: 6426419 (2002-07-01), Grubbs et al.
patent: 6635768 (2003-10-01), Herrmann et al.
patent: 7294717 (2007-11-01), Herrmann et al.
patent: 7329758 (2008-02-01), Grubbs et al.
patent: 7378528 (2008-05-01), Herrmann et al.
patent: 2003/0055262 (2003-03-01), Grubbs et al.
patent: 2008/0132708 (2008-06-01), Grubbs et al.
patent: 2008/0207911 (2008-08-01), Herrmann et al.
patent: 196 10 908 (1997-09-01), None
patent: 198 15 275 (1999-10-01), None
patent: 0 921 129 (1999-06-01), None
patent: 1 197 509 (2000-05-01), None
patent: 02000212192 (2000-08-01), None
patent: 96/04289 (1996-02-01), None
patent: WO 97/06185 (1997-02-01), None
patent: WO 97/20865 (1997-06-01), None
patent: WO 97/29135 (1997-08-01), None
patent: WO 99/51344 (1999-10-01), None
patent: WO 00/73366 (2000-05-01), None
patent: WO 00/71554 (2000-11-01), None
Weskamp et al., A Novel Class of Ruthenium Catalysts for Olefin Metathesis, Oct. 2, 1998, Angewandte Chemie, vol. 37, No. 18, pp. 2490-2493.
Herrmann et al., “N-Heterocyclic Carbenes,” Agnew. Chem. Int. Ed. Engl. 1997, 36, No. 19, 2162-2187.
Arduengo, III et al., “Electronic Stabilization of Nucleophilic Carbenes,” Journal of the American Chemical Society, Jul. 1, 1992, vol. 114, No. 14, 5530-5534.
Nguyen et al., “Syntheses and Activities of New Single-Component . . . Catalysts,” Journal of the American Chemical Society, Oct. 20, 1993, vol. 115, No. 21, 9858-9859.
Fu et al., “Catalytic Ring-Closing Metathesis . . . Carbene Complex,” Journal of the American Chemical Society, Oct. 20, 1993, vol. 115, No. 21, 9856-9857.
Schwab et al., “Synthesis and Applications of . . . Metathesis Activity,” Journal of the American Chemical Society, Jan. 10, 1996, vol. 118, No. 1, 100-110.
Dias et al., “Well-Defined Ruthenium . . . and Activity,” Journal of the American Chemical Society, Apr. 30, 1997, vol. 119, No. 17, 3887-3897.
Ulman et al., “Relative Reaction . . . Carbene Metathesis Initiators,” Organometallics, Jun. 8, 1998, vol. 17, No. 12, 2484-2489.
Dr. -Ing. H. W. Wanzlick, “Aspects of Nucleophilic Carbene Chemistry,” Angew. Chem. Internat. Edit., vol. 1 (1962), No. 2, 75-80.
Gonzalez et al., “Synthesis of . . . and Other Ligands,” Journal of the American Chemical Society, 1988, vol. 110, No. 13, 4419-4421.
Gregory J. Kubas, “Molecular Hydrogen . . . Transition Metals,” Accounts of Chemical Research, Mar. 1988, vol. 21. No. 3, 120-128.
Ivin, Kenneth J., Some recent applications of olefin metathesis in organic synthesis: A review, Journal of Molecular Catalysis A: Chemical. 1998, vol. 133, No. 1-2, pp. 1-16.
International Search Report, Dec. 23, 1999.
Poster Abstract from The Royal Society of Chemistry Dalton Division, 11thInternational Symposium on Homogeneous Catalysis, no later than Jul. 17, 1998.
Collins, T.J. et al. (1976). “Cyclic Transition-Metal Carbene Complexes from Ring-Closing Reactions on the .pi.-bound Substrates Carbon Disulfide and Carbon Diselenide. 1, 3-Dithiolan-2-ylidene and 1,3-Diselenolan-2-ylidene Complexes of Ruthenium(II) and Osmium(II),” Database Accession No. 84:135795 andJ. Organomet. Chem.107(3):C37-C39.
Demonceau, A. et al. (1997). “Novel Ruthenium-Based Catalyst Systems for the Ring-Opening Metathesis Polymerization of Low-Strain Cyclic Olefins,”Macromolecules30(11):3127-3136.
Dussel, R. et al. (1991). “Isocyanide Arene-Ruthenium(II) Complexes and Activation of Alkenylacetylenes: Synthesis and Characterization of Isocyanide Carbene-and Mixed Carene Ruthenium Compounds,”Organometallics10(9):3287-3291.
U.S. Appl. No. 60/135,493, filed May 24, 1999, Grubbs et al.
U.S. Appl. No. 60/142,853, filed Jul. 7, 1999, Grubbs et al.
Fürstner, A. et al. (1998). “Cationic Ruthenium Allenylidene Complexes as a New Class of Performing Catalysts for Ring Closing Meathesis,”Chemical Communications(12):1315-1316.
Herrmann, W.A. et al. (1998). “A Novel Class of Ruthenium Catalysts for Olefin Metathesis,” 11thInternational Symposium on Homogeneous CatalysisRetrieved from the Internet: URL:http://chsg-jrb1.st-and.ac.uk/conferences/ishc/posters/WeskampT.html on Sep. 6, 2002.
Jafarpour, L. et al. (1999). “(p-cymene)RuLC12(L=1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene and 1,3-Bis(2,6-diisopropylpheny)imidazol-2-ylidene) and Related Complexes as Ring Closing Metathesis Catalysts,”Organometallics18(18):3760-3763.
Köcher, C. (1997) “Neue Wege zu N-Heterocyclischen Carbenen und deren Metallkomplexen: Anwendungen in der Homogenkatalysy,” Dissertation, Technische Universitat Munchen. pp. 30-59 and 124-172.
Nguyen, S.T. et al. (1995). “The Syntheses and Activities of Polystyrene-Supported Olefin Metathesis Catalysts Based on C12(PR3)2Ru=CH-CH=CPh2,”J. Organometallic Chem. 497(1):195-200.
Roper, W.R. et al. (1982). “Reactions of a (dichlorocarbene)ruthenium Complex, RuC12(CC12)(CO)(PPh3)2,” Database Accession No. 98:34726 andJ. Organomet. Chem.233(3):C59-C63.
Schurer, S.C. et al. (2000). “Synthesis and Application of a Permanently Immobilized Olefin-Metathesis Catalyst,”Angewante Chemie International Edition39(21):3898-3901.
Ackermann, L. et al. (1999). “Ruthenium Carbene Complexes with Imidazolin-2-ylidene Ligands Allow the Formation of Tetrasubstituted Cycloalkenes by RCM,”Tetrahedron Letters40:4787-4790.
Scholl, M. et al. (1999). “Increased Ring Closing Metathesis Activity of Ruthenium-Based Olefin Methathesis Catalysts Coordinated with Imidazolin-2-ylidene Ligands,”Tetrahedron Letters40:2247-2250.
Scholl, M. et al. (1999). “Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligands,”Organic Letters1(6):953-956.
Weskamp, T. et al. (1999). “Highly Active Ruthenium Catalysts for Olefin Metathesis: The Synergy of N-Heterocyclic Carbenes and Coordinatively Labile Ligands,”Angew Chem. Int. Ed.(Communications) 38(16):2416-2419.
Schattenmann, Wolfgang C.: “Neue Katalysatoren für die Olefin-Metathese”, Dissertation, Technische Universität München, Nov. 12, 1997, XP001543131.
Furstner, Alois, et al., “Coordinatively unsaturated ruthenium allenylidene complexes: highly effective, well defined catalysts for the ring-closure metathesis of alpha,omega-dienes and dienynes”, Chem. Commun., Apr. 7, 1999, pp. 601-602.
Harlow, Karsten J., et al., “The first co-ordinatively unsaturated Group 8 allenylidene complexes: insights into Grubbs' vs. Dixneuf-Furstner olefin metathesis catalysts”, J. Chem. Soc., Dalton Trans., 1999, pp. 285-291.
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