Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-11-08
2005-11-08
Seaman, D. Margaret (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C546S304000, C544S224000
Reexamination Certificate
active
06962999
ABSTRACT:
Methods are provided for the construction of unsymmetrical biaryl compounds and alkylated aromatic compounds from arylnitriles using a nickel or palladium catalyzed coupling in which the catalyst has at least one phosphine or phosphite ligand.
REFERENCES:
patent: 4730032 (1988-03-01), Rossi et al.
patent: 4912276 (1990-03-01), Puckette
patent: 5128366 (1992-07-01), Hirai et al.
patent: 5130439 (1992-07-01), Lo et al.
patent: 5288895 (1994-02-01), Bouisset et al.
patent: 5364943 (1994-11-01), Rosen et al.
patent: 5559277 (1996-09-01), Beller et al.
patent: 5874808 (1999-02-01), Huang et al.
patent: 5922898 (1999-07-01), Miller et al.
patent: 6194599 (2001-02-01), Miller et al.
patent: 0 131 968 (1956-01-01), None
patent: 0 470 795 (2001-02-01), None
Cibulka, Collect Czech Chem Commun, vol. 64, pp 1159-1179, 1999.
Ali et al., 1992. “Palladium-catalysed cross-coupling reactions of arylboronic acids with π-deficient hsteroaryl chlorides,”Tetrahedron48(37):8117-6126.
Bleicher and Cosford, 1995, “Aryl-and heteroaryl-alkyne coupling reactions catalyzed by palladium on carbon and Cul in an aqueous medium,”SYNLETT11:1115-1116.
Bringmann et al., 1990, “The directed synthesis of biaryl compounds: modern concepts and strategies,”Angew, Chem, Int, Ed, Engl, 29:977-991.
Carinl et al., 1991, “Nonpeptide angiotensin II receptor antagonists: the discovery of a series of N-(biphenylymethyl)lmldazoles as potent, orally active antihypertansives,”J. Med. Chem. 34:2525-2547.
Clough et al., 1978, “Coupling of nonequivalent aromatic rings by soluble nickel catalysts. A general route to the 1.8-diaryinaphthalenes,”J. Org. Chem. 41(13):2252-2255.
Kallnin, V. N.. 1992, “Carbon-carbon bond formation in heterocydes using NI- and Pd-catalyzed reactions,”Synthesispp. 413-432.
Mantlo et al., 1991, “Potent orelly active imidazol[4,5-b]pyridine-based angiotensin II receptor antagonists,”J. Med. Chem.34:2918-2922.
Miller and Farrell, 1998, “Preparation of unsymmetrical biaryls via Ni- or Pd-catalyzed coupling of aryl chlorides with arylzincs,”Tetrahedron Letters39:6441-6444.
Miller and Farrell, 1998, “Synthesis of functionally substituted unsymmetrical biaryls via a novel double metal catalyzed coupling reaction,”Tetrahedron Letters39:7275-7278.
Miyaura et al., 1981, The palladium-catalyzed cross-coupling reaction of phenylboronic add with haloarenes in the presence of bases,Synthetic Communications11(7):513-519.
Negishi et al., 1977. “Selective Carbon-carbon bond formation via transition metal catalysis. 3. A highly selective synthesis of uneymmetrical biaryls and diarylmethanes by the nickel-or palladium-catalyzed reaction or aryl-and benzytzinc derivatives with arylhalides.”J. Org. Chem. 42(10):1821-1823.
Pridgen, L.N., 1982 “Oxazolines. 3. Regioselective synthesis of 2-(monosubstituted phenyl) and/or unsymmetrically 2-(disubetituted phenyl) 2-oxazolines by cross-coupling Grignard reagents to (haloaryl)-2-oxazolines,”J. Org. Chem.47:4319-4323.
Sainsbury, M., 1980, “Modern methods of ary-aryl bond formation,”Tetrahedron38:3327-3359.
Slanforth, S. P., 1998, “Catalytic cross-coupling reactions in biaryl synthesis,”Tetrahedron54:263-303.
Selto et al., 1995, “A synthesis of biaryls via nickel(0)-catalyzed cross-coupling reaction of chloroarenes with Phenylboronic acids,”Tetrahedron Letters37(17):2993-2996.
Tamao et al., 1976, Nickel-phosphine complex-catalyzed Grignard coupling. I. Cross-coupling of alkyl, aryl, and alkanyl Grignard reagents with aryl and alkenyl halides: general scope and llmitations,Bulletin of the Chemical Society of Japan49(7):1958-1969.
Whitall et al., 1996, “Organometallic complexes for nonlinear optics. 3. Molecular quadretic hyperpolarlzeblliues of ens, imine, and azo-linked ruthenium α-acetyldes: X-ray crystal structure of Ru(E)-4,4′-C CC6H4CH:CHC6H4NO2)(Pph3)(η-C5H5),”Organometallics15(7):1935-1941 (Abstract).
Zhu et al., 1991, “The direct formation of functionalized alkyl(aryl)zinc halides by oxidative addition of highly reactive zinc with organic halldes and their reactions with acid chlorides, α,β-unsaturated katones, and allylic, aryl and vinyl halides,”J. Org. Chem. 58:1445-1453.
Fuson, R.C. and W.S. Friedlander;“Displacement of substituants in phenyl 2,4,6-trilsoplylphenyl ketone by the action of Grignard reagants;” J. Am. Chem. Soc.; vol. 78, pp. 5410-5411 (1953).
Fuson, R.C. et al.: “The reaction of Grignard reagents with the cyanobanzoyidurenes,” J. Org. Chem.: vol. 16, pp. 648-654 (1951).
Miller, J.A.: “C-C Bond activation with selective functionalization; preparation of unsymmetrical blaryts from benzonitriles;” Tetrahedron Letters; vol. 42, pp. 6991-6993 (2001).
Milner, D.J.: “The mono-alkytdecyanation of tetrafluorolerephtalonitrile by reaction with Grignard reagents;” J. Organometallic Chem.; vol. 302, pp. 147-152 (1986).
Pharmacore, Inc.
Seaman D. Margaret
Townsend and Townsend / and Crew LLP
LandOfFree
Process for preparing unsymmetrical biaryls and alkylated... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for preparing unsymmetrical biaryls and alkylated..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing unsymmetrical biaryls and alkylated... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3497467