Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds

Hartwig, John F; Kawatsura, Motoi; Loeber, Oliver

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Title: Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds

Abstract

The present invention is directed to a process for addition of amines to carbon-carbon double bonds in a substrate, comprising: reacting an amine with a compound containing at least one carbon-carbon double bond in the presence a transition metal catalyst under reaction conditions effective to form a product having a covalent bond between the amine and a carbon atom of the former carbon-carbon double bond. The transition metal catalyst comprises a Group 8 metal and a ligand containing one or more 2-electron donor atoms. The present invention is also directed to enantioselective reactions of amine compounds with compounds containing carbon-carbon double bonds, and a calorimetric assay to evaluate potential catalysts in these reactions.

Inventors:

Hartwig, John F ^[1]; Kawatsura, Motoi ^[2]; Loeber, Oliver ^[3]

Durham, CT
Chatham, NJ
New Haven, CT

Issue Date:: Tue Jan 01 00:00:00 EST 2002

Research Org.:: Yale University (New Haven, CT)

OSTI Identifier:: 874407

Patent Number(s):: 6384282

Assignee:: Yale University (New Haven, CT)

Patent Classifications (CPCs):: C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C209/60 - by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
C07C211/44 - having amino groups bound to only one six-membered aromatic ring

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C07D295/15 - to an acyclic saturated chain

Show less

DOE Contract Number:: FG02-96ER14678

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: transition; metal-catalyzed; process; addition; amines; carbon-carbon; double; bonds; directed; substrate; comprising; reacting; amine; compound; containing; bond; presence; metal; catalyst; reaction; conditions; effective; form; product; covalent; carbon; atom; former; ligand; 2-electron; donor; atoms; enantioselective; reactions; compounds; calorimetric; assay; evaluate; potential; catalysts; transition metal; reaction conditions; double bond; /999/356/

Citation Formats


                    Hartwig, John F, Kawatsura, Motoi, and Loeber, Oliver. Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds.  United States: N. p., 2002. 
        Web.

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                    Hartwig, John F, Kawatsura, Motoi, & Loeber, Oliver. Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds.  United States.

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                    Hartwig, John F, Kawatsura, Motoi, and Loeber, Oliver. Tue .  
        "Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds".  United States.  https://www.osti.gov/servlets/purl/874407.

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@article{osti_874407,

  title        = {Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds},

  author       = {Hartwig, John F and Kawatsura, Motoi and Loeber, Oliver},

  abstractNote = {The present invention is directed to a process for addition of amines to carbon-carbon double bonds in a substrate, comprising: reacting an amine with a compound containing at least one carbon-carbon double bond in the presence a transition metal catalyst under reaction conditions effective to form a product having a covalent bond between the amine and a carbon atom of the former carbon-carbon double bond. The transition metal catalyst comprises a Group 8 metal and a ligand containing one or more 2-electron donor atoms. The present invention is also directed to enantioselective reactions of amine compounds with compounds containing carbon-carbon double bonds, and a calorimetric assay to evaluate potential catalysts in these reactions.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {Tue Jan 01 00:00:00 EST 2002},

  month        = {Tue Jan 01 00:00:00 EST 2002}

}

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Works referenced in this record:

Catalytic addition of secondary amines to ethylene (Contribution No. 1720)
journal, January 1971

Coulson, D. R.
Tetrahedron Letters, Vol. 12, Issue 5
https://doi.org/10.1016/S0040-4039(01)96459-7

Reaction between isoprene and aniline on complex palladium catalysts
journal, August 1992

Petrushkina, E. A.; Zakharkin, L. I.
Bulletin of the Russian Academy of Sciences Division of Chemical Science, Vol. 41, Issue 8
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Metal-Initiated Amination of Alkenes and Alkynes ^†
journal, April 1998

Müller, Thomas E.; Beller, Matthias
Chemical Reviews, Vol. 98, Issue 2
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Constrained Geometry Organolanthanide Catalysts. Synthesis, Structural Characterization, and Enhanced Aminoalkene Hydroamination/Cyclization Activity
journal, July 1999

Tian, Shun; Arredondo, Victor M.; Stern, Charlotte L.
Organometallics, Vol. 18, Issue 14
https://doi.org/10.1021/om990146a

Protonolysis approach to the catalytic amination of olefins with bis(phosphine)palladium(II) dialkyls
journal, March 1993

Seligson, Allen L.; Trogler, William C.
Organometallics, Vol. 12, Issue 3
https://doi.org/10.1021/om00027a026

The First Rhodium-Catalyzed Anti-Markovnikov Hydroamination: Studies on Hydroamination and Oxidative Amination of Aromatic Olefins
journal, April 1999

Beller, M.; Trauthwein, H.; Eichberger, M.
Chemistry - A European Journal, Vol. 5, Issue 4, p. 1306-1319
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Tetrahedron report number 144
journal, January 1983

Gasc, M. B.; Lattes, A.; Perie, J. J.
Tetrahedron, Vol. 39, Issue 5
https://doi.org/10.1016/S0040-4020(01)91847-2

The two component palladium catalyst system for intermolecular hydroamination of allenes
journal, August 1997

Al-Masum, Mohammad; Meguro, Masaki; Yamamoto, Yoshinori
Tetrahedron Letters, Vol. 38, Issue 34
https://doi.org/10.1016/S0040-4039(97)01370-1

Nickel- and Palladium-Catalyzed Additions of Nucleophiles to Cyclic 1,3-Dienes.
journal, January 1986

Andell, Ove S.; Bäckvall, Jan-E.; Moberg, Christina
Acta Chemica Scandinavica, Vol. 40b
https://doi.org/10.3891/acta.chem.scand.40b-0184

Amine-Catalyzed Addition of Azide Ion to α,β-Unsaturated Carbonyl Compounds
journal, October 1999

Guerin, David J.; Horstmann, Thomas E.; Miller, Scott J.
Organic Letters, Vol. 1, Issue 7
https://doi.org/10.1021/ol9909076

Nickel-catalyzed amination of 1,3-dienes Evidence for a π-allyl intermediate
journal, September 1974

Kiji, Jitsuo; Sasakawa, Eiichi; Yamamoto, Kazuyoshi
Journal of Organometallic Chemistry, Vol. 77, Issue 1
https://doi.org/10.1016/S0022-328X(00)89428-0

The [IrCl(Diphosphine)] ₂ /Fluoride System. Developing Catalytic Asymmetric Olefin Hydroamination
journal, November 1997

Dorta, Romano; Egli, Patrick; Zürcher, Fabio
Journal of the American Chemical Society, Vol. 119, Issue 44
https://doi.org/10.1021/ja972594k

Transition metal-catalysed addition reactions of H–heteroatom and inter-heteroatom bonds to carbon–carbon unsaturated linkages via oxidative additions
journal, January 1999

Han, Li-Biao; Tanaka, Masato
Chemical Communications, Issue 5
https://doi.org/10.1039/a806537c

Organolanthanide-Catalyzed Hydroamination/Cyclization. Efficient Allene-Based Transformations for the Syntheses of Naturally Occurring Alkaloids
journal, April 1999

Arredondo, Victor M.; Tian, Shun; McDonald, Frank E.
Journal of the American Chemical Society, Vol. 121, Issue 15
https://doi.org/10.1021/ja984305d

Palladium-Catalyzed Intermolecular Hydroamination of Vinylarenes Using Arylamines
journal, October 2000

Kawatsura, Motoi; Hartwig, John F.
Journal of the American Chemical Society, Vol. 122, Issue 39
https://doi.org/10.1021/ja002284t

Rhodium-Catalyzed Amination of Vinylpyridines: Hydroamination versus Oxidative Amination
journal, July 1999

Beller, Matthias; Trauthwein, Harald; Eichberger, Martin
European Journal of Inorganic Chemistry, Vol. 1999, Issue 7, p. 1121-1132
URL: 10.1002/(SICI)1099-0682(199907)1999:7<1121::AID-EJIC1121>3.0.CO;2-8

Asymmetric Synthesis of β-Amino Acid Derivatives via Catalytic Conjugate Addition of Hydrazoic Acid to Unsaturated Imides
journal, September 1999

Myers, Jason K.; Jacobsen, Eric N.
Journal of the American Chemical Society, Vol. 121, Issue 38
https://doi.org/10.1021/ja991621z

Rational design in homogeneous catalysis. Iridium(I)-catalyzed addition of aniline to norbornylene via nitrogen-hydrogen activation
journal, September 1988

Casalnuovo, Albert L.; Calabrese, Joseph C.; Milstein, David.
Journal of the American Chemical Society, Vol. 110, Issue 20
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Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization of Aminoalkynes
journal, January 1996

Li, Yanwu; Marks, Tobin J.
Journal of the American Chemical Society, Vol. 118, Issue 39
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Chiral Lewis Acid Catalysis in Conjugate Additions of O -Benzylhydroxylamine to Unsaturated Amides. Enantioselective Synthesis of β-Amino Acid Precursors
journal, July 1998

Sibi, Mukund P.; Shay, John J.; Liu, Mei
Journal of the American Chemical Society, Vol. 120, Issue 26
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?3-Allylpalladium Compounds
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Synthesis of allylic amines through the palladium-catalyzed hydroamination of allenes
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Besson, Laure; Goré, Jacques; Cazes, Bernard
Tetrahedron Letters, Vol. 36, Issue 22
https://doi.org/10.1016/0040-4039(95)00656-W

ChemInform Abstract: REACTION OF AMINES WITH 1,3-DIENES CATALYSED BY NICKEL COMPLEXES
journal, December 1974

Baker, Raymond; Cook, Alan H.; Halliday, Douglas E.
Chemischer Informationsdienst, Vol. 5, Issue 51
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Similar Records

Title: Transition metal-catalyzed process for addition of amines to carbon-carbon double bonds

Abstract

Citation Formats

Catalytic addition of secondary amines to ethylene (Contribution No. 1720) journal, January 1971

Reaction between isoprene and aniline on complex palladium catalysts journal, August 1992

Metal-Initiated Amination of Alkenes and Alkynes † journal, April 1998

Constrained Geometry Organolanthanide Catalysts. Synthesis, Structural Characterization, and Enhanced Aminoalkene Hydroamination/Cyclization Activity journal, July 1999

Protonolysis approach to the catalytic amination of olefins with bis(phosphine)palladium(II) dialkyls journal, March 1993

The First Rhodium-Catalyzed Anti-Markovnikov Hydroamination: Studies on Hydroamination and Oxidative Amination of Aromatic Olefins journal, April 1999

Tetrahedron report number 144 journal, January 1983

The two component palladium catalyst system for intermolecular hydroamination of allenes journal, August 1997

Nickel- and Palladium-Catalyzed Additions of Nucleophiles to Cyclic 1,3-Dienes. journal, January 1986

Amine-Catalyzed Addition of Azide Ion to α,β-Unsaturated Carbonyl Compounds journal, October 1999

Nickel-catalyzed amination of 1,3-dienes Evidence for a π-allyl intermediate journal, September 1974

The [IrCl(Diphosphine)] 2 /Fluoride System. Developing Catalytic Asymmetric Olefin Hydroamination journal, November 1997

Transition metal-catalysed addition reactions of H–heteroatom and inter-heteroatom bonds to carbon–carbon unsaturated linkages via oxidative additions journal, January 1999

Organolanthanide-Catalyzed Hydroamination/Cyclization. Efficient Allene-Based Transformations for the Syntheses of Naturally Occurring Alkaloids journal, April 1999

Palladium-Catalyzed Intermolecular Hydroamination of Vinylarenes Using Arylamines journal, October 2000

Rhodium-Catalyzed Amination of Vinylpyridines: Hydroamination versus Oxidative Amination journal, July 1999

Asymmetric Synthesis of β-Amino Acid Derivatives via Catalytic Conjugate Addition of Hydrazoic Acid to Unsaturated Imides journal, September 1999

Rational design in homogeneous catalysis. Iridium(I)-catalyzed addition of aniline to norbornylene via nitrogen-hydrogen activation journal, September 1988

Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization of Aminoalkynes journal, January 1996

Chiral Lewis Acid Catalysis in Conjugate Additions of O -Benzylhydroxylamine to Unsaturated Amides. Enantioselective Synthesis of β-Amino Acid Precursors journal, July 1998

?3-Allylpalladium Compounds journal, April 1985

Synthesis of allylic amines through the palladium-catalyzed hydroamination of allenes journal, May 1995

ChemInform Abstract: REACTION OF AMINES WITH 1,3-DIENES CATALYSED BY NICKEL COMPLEXES journal, December 1974

Catalytic addition of secondary amines to ethylene (Contribution No. 1720)
journal, January 1971

Reaction between isoprene and aniline on complex palladium catalysts
journal, August 1992

Metal-Initiated Amination of Alkenes and Alkynes ^†
journal, April 1998

Constrained Geometry Organolanthanide Catalysts. Synthesis, Structural Characterization, and Enhanced Aminoalkene Hydroamination/Cyclization Activity
journal, July 1999

Protonolysis approach to the catalytic amination of olefins with bis(phosphine)palladium(II) dialkyls
journal, March 1993

The First Rhodium-Catalyzed Anti-Markovnikov Hydroamination: Studies on Hydroamination and Oxidative Amination of Aromatic Olefins
journal, April 1999

Tetrahedron report number 144
journal, January 1983

The two component palladium catalyst system for intermolecular hydroamination of allenes
journal, August 1997

Nickel- and Palladium-Catalyzed Additions of Nucleophiles to Cyclic 1,3-Dienes.
journal, January 1986

Amine-Catalyzed Addition of Azide Ion to α,β-Unsaturated Carbonyl Compounds
journal, October 1999

Nickel-catalyzed amination of 1,3-dienes Evidence for a π-allyl intermediate
journal, September 1974

The [IrCl(Diphosphine)] ₂ /Fluoride System. Developing Catalytic Asymmetric Olefin Hydroamination
journal, November 1997

Transition metal-catalysed addition reactions of H–heteroatom and inter-heteroatom bonds to carbon–carbon unsaturated linkages via oxidative additions
journal, January 1999

Organolanthanide-Catalyzed Hydroamination/Cyclization. Efficient Allene-Based Transformations for the Syntheses of Naturally Occurring Alkaloids
journal, April 1999

Palladium-Catalyzed Intermolecular Hydroamination of Vinylarenes Using Arylamines
journal, October 2000

Rhodium-Catalyzed Amination of Vinylpyridines: Hydroamination versus Oxidative Amination
journal, July 1999

Asymmetric Synthesis of β-Amino Acid Derivatives via Catalytic Conjugate Addition of Hydrazoic Acid to Unsaturated Imides
journal, September 1999

Rational design in homogeneous catalysis. Iridium(I)-catalyzed addition of aniline to norbornylene via nitrogen-hydrogen activation
journal, September 1988

Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization of Aminoalkynes
journal, January 1996

Chiral Lewis Acid Catalysis in Conjugate Additions of O -Benzylhydroxylamine to Unsaturated Amides. Enantioselective Synthesis of β-Amino Acid Precursors
journal, July 1998

?3-Allylpalladium Compounds
journal, April 1985

Synthesis of allylic amines through the palladium-catalyzed hydroamination of allenes
journal, May 1995

ChemInform Abstract: REACTION OF AMINES WITH 1,3-DIENES CATALYSED BY NICKEL COMPLEXES
journal, December 1974