Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1997-09-19
1998-10-06
Burn, Brian M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
544163, 544178, 546192, 546205, 558422, 564396, 564408, C07C20922
Patent
active
058178775
ABSTRACT:
A process of preparing an organic amine having at least one unsaturated group, such as an arylamine, involving contacting an unsaturated organic sulfonate, such as an aryl sulfonate, with a reactant amine, such as an alkyl or aryl amine, in the presence of a base and a transition metal catalyst under reaction conditions. The transition metal catalyst contains a Group 8 metal and a chelating ligand, for example a Group 15-substituted arylene or Group 15-substituted metallocene, such as 1,1'-bis(diphenylphosphino)-2,2'-binaphthyl or 1,1'-bis(diphenylphosphino)-ferrocene, respectively. The aryl sulfonate can be prepared from a phenol and sulfonating agent.
REFERENCES:
patent: 5576460 (1996-11-01), Buchwald et al.
J. P. Wolfe and S. L. Buchwald, "Palladium-Catalyzed Amination of Aryl Triflates," Journal of the American Chemical Society, 62 (No. 5), 1997, 1264-1267.
J. Louie and J. F. Hartwig, "Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides. Mechanistic Studies Lead to Coupling in the Absence of Tin Reagents," Tetrahedron Letters, 36 (No. 21), 1995, 3609-3612.
J. Louie, M. S. Driver, B. C. Hamann, and J. F. Hartwig, "Palladium-Catalyzed Amination of Aryl Triflates and Importance of Triflate Addition Rate," Journal of Organic Chemistry, 62 (No. 5), 1997, 1268-1273.
H. Kotsuki et al., "High Pressure Organic Chemistry; XI. A New Convenient Synthesis of Aromatic Amines from Activated Phenols," Synthesis, Dec. 1990, 1145-1146.
J. P. Wolfe, R. A. Rennels, and S. L. Buchwald, "Intramolecular Palladium-Catalyzed Aryl Amination and Aryl Amidation," Tetrahedron, 52 (No. 21), 1996, 7525-7546.
M. S. Driver and J. F. Hartwig, "A Second Generation Catalyst for Aryl Halide Amination: Mixed Secondary Amines from Aryl Halides and Primary Amines Catalyzed by (DPPF)PdCl.sub.2," Journal of the American Chemical Society, 118 (No. 30), 1996, 7217-7218.
J. P. Wolfe et al., "An Improved Catalyst System for Aromatic Carbon-Nitrogen Bond Formation: The Possible Involvement of Bis(Phosphine)Palladium Complexes as Key Intermediates," Journal of the American Chemical Society, Communications, 118 (No. 30), 1996, 7215-7216.
J. P. Wolfe and S. L. Buchwald, "Palladium-Catalyzed Amination of Aryl Iodides," Journal of Organic Chemistry, 61 (No. 3), 1996, 1133-1135.
A. S. Guram et al., "A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines," Angew. Chem. Int. Ed. Engl., 34 (No. 12), 1995, 1348-1350.
V. Farina et al., "Palladium-Catalyzed Coupling of Arylstannanes with Organic Sulfonates: A Comprehensive Study," Journal of Organic Chemistry, 58 (No. 20), 1993, 5434-5444.
Ng Ph. Buu-Hoi, "The Scope of the Knoevenagel Synthesis of Aromatic Secondary Amines," Journal of the Chemical Society, 1952, 4346-4349.
R. A. Rossi and J. F. Bunnett, "A General Conversion of Phenols to Anilines," Journal of Organic Chemistry, Communications, 37 (1972), 3570.
H. Seeboth, "The Bucherer Reaction and the Preparative Use of its Intermediate Products," Angew. Chem. International Edition, 6 (No. 4), 1967, 307-317.
Driver Michael S.
Hamann Blake
Hartwig John F.
Louie Janis
Burn Brian M.
Yale University
Zuckerman Marie F.
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