Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-07-24
2007-07-24
Wilson, James O. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C556S413000, C564S015000
Reexamination Certificate
active
11229043
ABSTRACT:
One aspect of the present invention relates to novel ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.
REFERENCES:
patent: 4604474 (1986-08-01), Kumobayashi et al.
patent: 4691037 (1987-09-01), Yoshikawa et al.
patent: 4739084 (1988-04-01), Takaya et al.
patent: 4739085 (1988-04-01), Takaya et al.
patent: 4954644 (1990-09-01), Sayo et al.
patent: 4992519 (1991-02-01), Mukherjee et al.
patent: 4994590 (1991-02-01), Takaya et al.
patent: 5012002 (1991-04-01), Kumobayashi et al.
patent: 5144050 (1992-09-01), Chan et al.
patent: 5206399 (1993-04-01), Sayo et al.
patent: 5223632 (1993-06-01), Ishizaki et al.
patent: 5231202 (1993-07-01), Hayashi et al.
patent: 5274146 (1993-12-01), Ishizaki et al.
patent: 5312939 (1994-05-01), Hori et al.
patent: 5347045 (1994-09-01), Herrmann et al.
patent: 5481045 (1996-01-01), Herrmann et al.
patent: 5510503 (1996-04-01), Laue et al.
patent: 5510554 (1996-04-01), Regnat et al.
patent: 5565398 (1996-10-01), Herrmann et al.
patent: 5631393 (1997-05-01), Kohlpaintner et al.
patent: 5648548 (1997-07-01), Takaya et al.
patent: 5663426 (1997-09-01), Albanese et al.
patent: 5693868 (1997-12-01), Sayo et al.
patent: 5710337 (1998-01-01), Unruh et al.
patent: 5710338 (1998-01-01), Unruh et al.
patent: 5736480 (1998-04-01), Davis et al.
patent: 5756760 (1998-05-01), Miyano et al.
patent: 5756838 (1998-05-01), Davis et al.
patent: 5767276 (1998-06-01), Zhang
patent: 5777087 (1998-07-01), Kohlpaintner et al.
patent: 5780692 (1998-07-01), Sakaguchi et al.
patent: 5789609 (1998-08-01), Tamao et al.
patent: 5789624 (1998-08-01), Unruh et al.
patent: 5808162 (1998-09-01), Sayo et al.
patent: 5817877 (1998-10-01), Hartwig et al.
patent: 5824830 (1998-10-01), Ikariya et al.
patent: 5827794 (1998-10-01), Davis et al.
patent: 5847222 (1998-12-01), Yokozawa et al.
patent: 5977361 (1999-11-01), Hartwig et al.
patent: 6100398 (2000-08-01), Hartwig et al.
patent: 6143834 (2000-11-01), Tamao et al.
patent: 6307087 (2001-10-01), Buchwald et al.
patent: 6395916 (2002-05-01), Buchwald et al.
patent: 0118257 (1984-09-01), None
patent: 0135392 (1985-03-01), None
patent: 0156607 (1985-10-01), None
patent: 0174056 (1986-03-01), None
patent: 0174057 (1986-03-01), None
patent: 0118257 (1986-12-01), None
patent: 0235450 (1987-09-01), None
patent: 0135392 (1988-02-01), None
patent: 0174057 (1988-08-01), None
patent: 0156607 (1988-11-01), None
patent: 0466405 (1992-01-01), None
patent: 0503884 (1992-09-01), None
patent: 0466405 (1995-02-01), None
patent: 0667350 (1995-08-01), None
patent: 0731105 (1996-11-01), None
patent: 0802173 (1997-10-01), None
patent: 0826694 (1998-03-01), None
patent: 0849274 (1998-06-01), None
patent: 0647648 (1999-03-01), None
patent: 07330786 (1995-12-01), None
patent: 8311090 (1996-11-01), None
patent: 09235289 (1997-09-01), None
patent: WO 95/22405 (1995-08-01), None
patent: WO 98/12202 (1998-03-01), None
patent: WO 98/15515 (1998-04-01), None
Aranyos et al., “Novel Electron-Rich Bulky Phosphine Ligands Facilitate the Palladium-Catalyzed Preparation of Diaryl Ethers”, J. AM. Chem. Soc. 121: 4369-4378 (1999).
Bayston et al.; “Preparation and Use of a Polymer Supported BINAP Hydrogenation Catalyst”, J.Org. Chem. 63:3137-3140, (1998).
Bei, X. et al., “A Convenient Palladium/Ligand Catalyst for Suzuki Cross-Coupling Reactions of Arylboronic Acids and Aryl Chlorides”, Tetrahedron Letters, 40:3855-3858 (1999).
Bei, X. et al., “General and Efficient Palladium-Catalyzed Aminations of Aryl Chlorides”, Tetrahedron Letters, 40:1237-1240 (1999).
Bei, X. et al., “Phenyl Backbone-Derived P,O- and P,N-Ligands for Palladium/Ligand-Catalyzed Aminations of Aryl Bromides, Iodides, and Chlorides. Synthesis and Structures of (P,O)n-Palladium(II)Aryl(Br) Complexes”, Organometallics, 18:1840-1853 (1999).
Beller, M. et al., “First Palladium-Catalyzed Aminations of Aryl Chlorides”, Tetrahedron Letters, 38:2073-2074 (1997).
Beller, M., “Palladacycles as Efficient Catalysts for Aryl Coupling Reactions”, Agnew. Chem. Int. Ed. Engl., 34:1848-1849 (1995).
Brenner, E. et al., “New Efficient Nickel(0) Catalysed Amination of Aryl Chlorides”, Tetrahedron Letters, 39:5359-5362 (1998).
Bronco, S. and Consiglio, G., “Regio- and Stereoregular Copolymerisation of Propene with Carbon Monoxide Catalysed by Palladium Complexes Containing Atropisomeric Diphosphine Ligands”, Macromol. Chem. Phys. 197: 355-365 (1996).
Bumagin, N. et al., “Ligandless Palladium catalyzed Reactions of Arylboronic Acids and Sodium Tetraphenylborate with Aryl Halides in Aqueous Media”, Tetrahedron, 53:14437-14450 (1997).
Chemical Abstracts vol. 123; No. 15, Oct. 9, 1995, Abstract No. 197945; Colombus, Ohio, US.
Chemical Abstracts vol. 124 No. 25, Jun. 17, 1996; Abstract No. 343650, Colombus Ohio, US.
Chemical Abstracts vol. 127 No. 21; Nov. 24, 1997, Abstract No. 293410, Colombus Ohio.
Cho, S. Y. et al, “The assymetric synthesis of cyclopentane derivatives by palladium-catalyzed coupling of prochiral alkylboron compounds”, Tetrahedron:Assymetry, 9:3751-3754 (1998).
Cho, Y. S. and Shibasaki, M.; “Synthesis and Evaluation of a New Chiral Ligand: 2- diphenylarsino-2′ -diphenylphosphino-1,1′ -binaphthyl (BINAPAS)”, Tetrahedron Letters 39 : 1773-1776 (1998).
Cornils, B., “Industrial Aqueous Biphasic Catalysis: Status and Directions”, Org. Proc. Res. Dev., 2:121-127 (1998).
Crameri et al., “Pratical Synthesis of (S)2(4fluorophenyl)3methylbutanoic acid, key building block for the calcium antagonist Mibefradil”, Tetrahedron : Asymmetry 8 (21): 3617-3623 (1997).
Database CAPLUS on STN Chemical Abstract (Columbus, Ohio USA), Old et al., CA 133:43406 “Efficient Palladium-Catalyzed N-Arylation of Indoles” abse of Organic Letters. 200, vol. 2, No. 10, pp. 1403-1406.
Database CAPLUS on STN Chemical Abstracts (Columbus, Ohio USA) Fabbri et al., CA:121:108962 “Binaphthyl-substituted chiral phosphines and oxides from binaphthophospholes and nucleophiles” abs of Synethetic Comm., 1994, vol. 24, No. 9, pp. 1271-1278.
Database CAPLUS on STN Chemical Abstracts (Columbus, Ohio USA) Tomori et al. CA:133:266921 “An Improved Synthesis of Functionalized Biphneyl-Based Phosphine Ligands” abs of Journal of Organic Chemistry. 2000, vol. 65, No. 17, pp. 5334-5341.
Database CAPLUS on STN Chemical Abstracts (Columbus, Ohio USA), Huang et al., CA:139:117168 Expanding Pd-Catalyed Bond Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination and Complementary with Cu-Catalyzed Reactions, abs of J. Amer. Chem. Soc. 2003, vol. 125, No. 22, pp. 6653-6655.
Database CAPLUS on STN Chemical Abstracts (Columbus, Ohio USA), Van Der Winkel et al., CA:114:229033 “Investigations of highly crowded phosphino lambda 3, lambda 5-diphosphaphenanthrene” abs of Heteroatom Chemistry. 1991, vol. 2, No. 1, pp. 17-28.
David W. Old et al., “A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Temperature Suzuki Couplings and Amination of Unactivated Aryl Chlorides,” J. Am. Chem. Soc., vol. 120, pp. 9722-9723 (1998).
Ding, K. et al., “Highly Efficient and Pratical Optical Resolution of 2Amino2′hydroxy1,1′binaphthyl by Molecular Complexation with N-Benzylcinchonidium Chloride: A Direct Transformation to Binaphthyl Amino Phosphine”, Chem. Eur. J. 5 (6): 1734-1737 (1999).
Driver M. S. and Hartwig F. J. A Second Generation Catalyst for Aryl Halide Animation : Mixed Secondary Amines From Aryl Halides and Primary Amines Catalyzed by (DPPF) PdCl2 ), J. Am. Chem. Soc. 118 : 7217-7218 (1996)
Buchwald Stephen L.
Kamikawa Ken
Old David W.
Palucki Michael
Wolfe John P.
Foley & Hoag LLP
Gordon Dana M.
Massachusetts Institute of Technology
Sackey Ebenezer
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