Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2008-01-24
2009-06-02
Puttlitz, Karl J. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C564S012000, C564S013000, C564S014000
Reexamination Certificate
active
07541462
ABSTRACT:
Methods and compounds are provided for the formation of carbon-nitrogen or carbon-carbon bonds comprising reacting an amine or an aryl boronic acid with an aryl halide in the presence of a palladium catalyst, a base, and a compound of formula II:
REFERENCES:
patent: 2005/0176978 (2005-08-01), Verkade et al.
B.L.Laube, R.D.Bertrand, G.A.Casedu. R.D.Compton, J.G.Verkade, Polycyclic Group V Ligands, III, Inorganic Chemistry, 1967, vol. 6, No. 1, pp. 173-176.
S.Urgaonkar, M.Nagarajan, J.G.Verkade, P[N(i-Bu)CH2CH2]3N: A versatile ligand for the Pd-Catalyzed amination of aryl chlorides, Organic Letters, 2003, vol. 5, No. 6, pp. 815-818.
U.S. Appl. No. 10/989,538, Restriction Requirement mailed Sep. 24, 2007, 7 pgs.
U.S. Appl. No. 11/236,877, Notice of Allowance mailed Dec. 27, 2007, 7 pgs.
U.S. Appl. No. 11/236,877 Non Final Office Action mailed Jul. 3, 2007, 7 pgs.
U.S. Appl. No. 11/236,877, Response filed Oct. 3, 2007 to Non-Final Office Action mailed Jul. 3, 2007., 8 pgs.
Clardy, J.C., et al., “Crystal and Molecular Structures of the Caged Amino Phosphorus Molecules OP(NMeCH2)3CMe and H3BP(NMeCH2)3CMe”,Phosphorus, 4(3), (1974), 133-141.
Cowley, A H., et al., “A UV Photoelectron Spectroscopic Investigation of Some Polycyclic Group VA Compounds and Related Acyclic Species. Part I: Free and Coordinated Aminophosphines and Related Compounds”,Inorg. Chem., 21, (1981),543-9.
Crochet, P., et al., “New Flouroionophores from Aniline Dimer Derivatives: a Variation of Cation Signalling Mechanism With the Number of Amino Groups”,Chem. Commun., (2000), 289-290.
De Silva, A. P., et al., “Signaling Recognition Events with Fluorescent Sensors and Switches”,Chem Rev., 97(5), School of Chemistry, Queen's University, Belfast BT9 5AG, Northern Ireland,(1997),1515-66.
Driver, MS., et al., “A Second-Generation Catalyst for Aryl Halide Amination: Mixed Secondary Amines from Aryl Halides and Primary Amines Catalyzed by (DPPF)PdCI2”,Amer. Chem. Soc., 118(30), (Jul. 1996), 7217-7218.
Fleischer, E. B., et al., “Conversion of Aliphatic and Alicyclic Polyalcohols to the Corresponding Primary Polyamines, 36”,J. Org. Chem, 36, (1971), 3042-3044.
Friedrich, M., et al., “Easy Access to Derivatives of 2-(Hydroxymethyl)propane-1,2,3-triol (Isoerythritol) with up to Four Separately Addressable Functionalities”,Journal of Organic Chemistry, 34(39), (2003), 2138-2143.
Grasa, G., “Animation Reactions of Aryl Halides with Nitrogen Containing reagents Mediated by Palladium / Imidazolium Salt systems”,Journal of Organic Chemistry, 66, (2001), 7729-7737.
Greco, G. E., et al., “Synthesis of Aryl-substituted Triamidoamine Ligands and Molybdenum (IV) Complexes that Contain Them”,Organomatallics, 17(26), (1998), 5591-5593.
Hartwig, J. F., et al., “Room-Temperature Palladium-Catalyzed Amination of Aryl Bromides and Chlorides and Extended Scope of Aromatic C-N and Chlorides and Extended Scope of Aromatic C-N”,J. Org. Chem., 64, (1999), 5575-5580.
Hirano, T., et al., “Novel-Zinc Fluorescent Probes Excitable with Visible Light for Biological Applications”,Angew. Chem. Int. Ed., 39(6), (2000), 1052-1054.
Kataoka, Noriyasu , et al., “Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C-C, C-N, and C-O Bond-Forming Cross-Couplings”,J. Org. Chem., 67, (2002), 5553-5566.
Laube, B L., et al., “Polycyclic Group V Ligands. III. 2,6,7-Trimethyl-4methyl-2,6,7-friaza1-phosphabicyclo[2.2.2] octane. A Bidentate Donor”,Inorganic Chemistry, 6, (Jan. 1967), 173-176.
Litke, Adam F., et al., “Versatile catalysts for the suzuki cross coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions”,Journal of the American Chemical Society, 122, (2000), 4020-4028.
Littke, Adam F., et al., “Palladium-catalyzed coupling reactions of aryl chlorides”,Angew. Chem. Int. Ed., 41, (2002), 4176-4211.
Lohr, H.-G., et al., “Chromo- and Fluoroionophores. A New Class of Dye Reagents”,Acc. Chem. Res., 18, (1985), 65-72.
Matsumoko, K., et al., “Ag+Ion-selective lariat ethers: high pressure syntheses and cation recognition properties”,J. Chem. Soc. Perkins Trans., (1995), 2497-2502.
Miyaura, N., et al., “Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds”,Chem. Rev., 95, (1995),2457-83.
Moloy, K. G., et al. “N-Pyrrolyl Phosphines: An Unexploited Class of Phosphine Ligands with Exceptional n-Acceptor Character”,J. Am. Chem. Soc., 117, (1995), 7696-7710.
Muci, A. R., et al., “Practical Palladium Catalysts for C-N and C-O Bond Formation”,Topics in Current Chemistry, 219, (2002), 133-209.
Nishiyama, M., et al., “Synthesis of N-Arylpiperazines from Aryl Halides and Piperazine under a Palladium Tri-tert-butylphosphine Catalyst”,Tetrahedron Letters, 39, (1998), 617-620.
Romming, C., et al., “Structural Studies on the Phosphorus-Nitrogen Bond. II. The Crystal Structure of Tris(morpholino)phosphine Selenide, Tris(piperidino)phosphine Selenide, and Tris(dimethylamino)-phosphine Selenide”,Acta Chemica Scandinavica A, 33, (1979), 187-197.
Romming, C., et al., “Structural Studies on the Phosphorus-Nitrogen Bond. IV. The Crystal Structure of Ttris(morpholino)arsine. A Comparision With the Crystal Structure of Tri(morpholino)phosphine”,Acta Chemica Scandinavica A, 34, (1980), 365-373.
Socol, S. M., et al., “Ligation of Phosphorous Ligands to Silver(1). 1. Coordination of One to Four P(NR2)3Ligands and the Structure of a Nonlinear Two-Coordinate Complex”,Inorg. Chem., 23, (1984), 88-94.
Stanforth, S. P., “Catalytic Cross-coupling Reactions in Biaryl Synthesis”,Tetrahedron, 54, (1998), 263-303.
Su, W., et al., “Pd2(dba)3/P(i-BuNCH2CH2)3N-Catalyzed Stille Cross-Coupling of Aryl Chlorides”,Organic Letters, 6(9), (2004), 1421-1424.
Urgaonkar, S., et al., “Application of a New Bicyclic Triaminophosphine Ligand in Pd-Catalyzed Buchwald-Hartwig Amination Reactions of Aryl Chlorides, Bromides, and Iodides”,J. Org. Chem., 68, (2003), 8416-8423.
Urgaonkar, S., et al., “P(iBuNCH2CH2)3N: an Effective Ligand in the Palladium-Catalyzed Amination of Aryl Bromides and Iodides.”,Journal of Organic Chemistry, 68(2), (2003), 452-459.
Urgaonkar, S., et al., “P[N(i-Bu)CH2CH2]3N: a Versatile Ligand for the Pd-Catalyzed Amination of Aryl Chlorides”,Organic Letters, 5(6), (2003), 815-818.
Urgaonkar, S., et al., “Palladium/Proazaphosphatrane-Catalyzed Amination of Aryl Halides Possessing in a Phenol, Alcohol, Acetanilide, Amide or an Enolizable Ketone Functional Group:Efficacy of Lithium Bis(trimethylsilyl)amide as the Base”,Adv. Synth. Catal., 346, (2004), 611-616.
Urgaonkar, S., et al., “Pd/P(i-BuNCH2CH2)3N: an Efficient Catalyst for Suzuki Cross-Coupling of Aryl Bromides and Chlorides with Arylboronic Acids”,Tetrahedron Letters, 43, (2002), 8921-8924.
Urgaonkar, S., “Synthesis of N-aryl-aza-crown ethers via Pd-catalyzed amination reactions of aryl chlorides with aza-crown ethers”,Tetrahedron, 60, (2004),11837-11842.
Verkade, J . , “P(RNCH2CH2)3N: Very Strong Non-Ionic Bases Useful in Organic Synthesis”,Topics in Current Chemistry, 223, (2003), 3-40.
Verkade, J., et al., “Recent Applications of Proazaphosphatranes in Organic Synthesis”,Adrichema Acta, 37(1), (2004),3-26.
Verkade, J., et al., “Triaminophosphate Ligands for Carbon-Nitrogen and Carbon-Carbon Bond Formation”, U.S. Appl. No. 11/236,877, filed Sep. 27, 2005, 49 pgs.
Witulski, B. et al., “N-(9-Anthryi)aza-18-crown-6: Palladium-catalysed Synthesis, Photophysical Properties and Cation Binding Ability”,Tetrahedron Letters, 39, (1998), 4807-4808.
Witulski, B., et al., “Novel Alkali Cation Chemosensors Based onN-9-Anthrylaza-crown Ethers”,Organic Letters, 3(1
Urgaonkar Sameer
Verkade John G.
Xu JuHua
Haukaas Michael H.
Iowa State University & Research Foundation, Inc.
Katakam Sudhakar
Puttlitz Karl J.
Schwegman Lundberg & Woessner, P.A.
LandOfFree
Triaminophosphine ligands for carbon-nitrogen and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Triaminophosphine ligands for carbon-nitrogen and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Triaminophosphine ligands for carbon-nitrogen and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4064765