Buchwald–Hartwig amination (English Wikipedia)

Analysis of information sources in references of the Wikipedia article "Buchwald–Hartwig amination" in English language version.

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  • Forero-Cortés, Paola A.; Haydl, Alexander M. (2 July 2019). "The 25th Anniversary of the Buchwald–Hartwig Amination: Development, Applications, and Outlook". Organic Process Research & Development. 23 (8): 1478–1483. doi:10.1021/acs.oprd.9b00161. S2CID 198366762.
  • Kosugi, M.; Kameyama, M.; Migita, T. (1983), "Palladium-Catalyzed Aromatic Amination of Aryl Bromides With n,n-Di-Ethylamino-Tributyltin", Chemistry Letters, 12 (6): 927–928, doi:10.1246/cl.1983.927
  • Boger, D.L.; Panek, J.S. (1984), "Palladium(0)- mediated [beta]-carboline synthesis: Preparation of the CDE ring system of lavendamycin", Tetrahedron Letters, 25 (30): 3175–3178, doi:10.1016/S0040-4039(01)91001-9
  • Paul,F.; Patt, J.; Hartwig, J.F. (1994), "Palladium-catalyzed formation of carbon-nitrogen bonds. Reaction intermediates and catalyst improvements in the hetero cross-coupling of aryl halides and tin amides", J. Am. Chem. Soc., 116 (13): 5969–5970, doi:10.1021/ja00092a058
  • Guram, A.S.; Buchwald, S.L. (1994), "Palladium-Catalyzed Aromatic Aminations with in situ Generated Aminostannanes", J. Am. Chem. Soc., 116 (17): 7901–7902, doi:10.1021/ja00096a059
  • Louie,J.; Hartwig, J.F. (1995), "Palladium-catalyzed synthesis of arylamines from aryl halides. Mechanistic studies lead to coupling in the absence of tin reagents", Tetrahedron Letters, 36 (21): 3609–3612, doi:10.1016/0040-4039(95)00605-C
  • Guram, A.S.; Rennels, R.A.; Buchwald, S.L. (1995), "A Simple Catalytic Method for the Conversion of Aryl Bromides to Arylamines", Angewandte Chemie International Edition, 34 (12): 1348–1350, doi:10.1002/anie.199513481
  • Muci, A.R.; Buchwald, S.L. (2002), "Practical Palladium Catalysts for C–N and C–O Bond Formation", Topics in Curr. Chem., Topics in Current Chemistry, 219: 131–209, doi:10.1007/3-540-45313-x_5, ISBN 978-3-540-42175-7
  • Driver, M.S.; Hartwig, J.F. (1997), "Carbon−Nitrogen-Bond-Forming Reductive Elimination of Arylamines from Palladium(II) Phosphine Complexes", J. Am. Chem. Soc., 119 (35): 8232–8245, doi:10.1021/ja971057x
  • Hartwig, J.F.; Richards, S.; Barañano, D.; Paul, F. (1996), "Influences on the Relative Rates for C−N Bond-Forming Reductive Elimination and β-Hydrogen Elimination of Amides. A Case Study on the Origins of Competing Reduction in the Palladium-Catalyzed Amination of Aryl Halides", J. Am. Chem. Soc., 118 (15): 3626–3633, doi:10.1021/ja954121o
  • Driver, M.S.; Hartwig, J.F. (1995), "A Rare, Low-Valent Alkylamido Complex, a Diphenylamido Complex, and Their Reductive Elimination of Amines by Three-Coordinate Intermediates", J. Am. Chem. Soc., 117 (16): 4708–4709, doi:10.1021/ja00121a030
  • Widenhoefer, R.A.; Buchwald, S.L. (1996), "Halide and Amine Influence in the Equilibrium Formation of Palladium Tris(o-tolyl)phosphine Mono(amine) Complexes from Palladium Aryl Halide Dimers", Organometallics, 15 (12): 2755–2763, doi:10.1021/om9509608
  • Hartwig, J.F. (1999), "Approaches to catalyst discovery. New carbon-heteroatom and carbon-carbon bond formation", Pure Appl. Chem., 71 (8): 1416–1423, doi:10.1351/pac199971081417, S2CID 34700080
  • Hartwig, J.F. (1997), "Palladium-Catalyzed Amination of Aryl Halides: Mechanism and Rational Catalyst Design", Synlett, 1997 (4): 329–340, doi:10.1055/s-1997-789, S2CID 196704196
  • Hartwig, J.F. (1998), "Carbon-Heteroatom Bond-Forming Reductive Eliminations of Amines, Ethers, and Sulfides", Acc. Chem. Res., 31: 852–860, doi:10.1021/ar970282g
  • Wolfe, J.P.; Wagaw, S.; Marcoux, J.F.; Buchwald, S.L. (1998), "Rational Development of Practical Catalysts for Aromatic Carbon-Nitrogen Bond Formation", Acc. Chem. Res., 31: 805–818, doi:10.1021/ar9600650
  • Hartwig, J.F. (1998), "Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism", Angew. Chem. Int. Ed., 37 (15): 2046–2067, doi:10.1002/(sici)1521-3773(19980817)37:15<2046::aid-anie2046>3.0.co;2-l, PMID 29711045
  • Hartwig, J.F. (2008), "Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides", Acc. Chem. Res., 41 (11): 1534–1544, doi:10.1021/ar800098p, PMC 2819174, PMID 18681463
  • Surry, D.S.; Buchwald, S.L. (2008), "Biaryl Phosphane Ligands in Palladium-Catalyzed Amination", Angew. Chem. Int. Ed., 47 (34): 6338–6361, doi:10.1002/anie.200800497, PMC 3517088, PMID 18663711
  • Surry, D.S.; Buchwald, S.L. (2011), "Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide", Chem. Sci., 2 (1): 27–50, doi:10.1039/c0sc00331j, PMC 3306613, PMID 22432049
  • Wolfe, J. P.; Buchwald, S. L. (1996), "Palladium-Catalyzed Amination of Aryl Iodides", J. Org. Chem., 61 (3): 1133–1135, doi:10.1021/jo951844h
  • Driver, M.S.; Hartwig, J.F. (1996), "A Second-Generation Catalyst for Aryl Halide Amination: Mixed Secondary Amines from Aryl Halides and Primary Amines Catalyzed by (DPPF)PdCl2", J. Am. Chem. Soc., 118 (30): 7217–7218, doi:10.1021/ja960937t
  • Wolfe, J.P.; Wagaw, S.; Buchwald, S.L. (1996), "An Improved Catalyst System for Aromatic Carbon-Nitrogen Bond Formation: The Possible Involvement of Bis(Phosphine) Palladium Complexes as Key Intermediates", J. Am. Chem. Soc., 118: 7215–7216, doi:10.1021/ja9608306
  • Louie, J.; Driver, M.S.; Hamann, B.C.; Hartwig, J.F. (1997), "Palladium-Catalyzed Amination of Aryl Triflates and Importance of Triflate Addition Rate", J. Org. Chem., 62 (5): 1268–1273, doi:10.1021/jo961930x
  • Wagaw, S.; Rennels, R.A.; Buchwald, S.L. (1997), "Palladium-Catalyzed Coupling of Optically Active Amines with Aryl Bromides", J. Am. Chem. Soc., 119 (36): 8451–8458, doi:10.1021/ja971583o
  • Old, D.W.; Wolfe, J.P.; Buchwald, S.L. (1998), "A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Temperature Suzuki Couplings and Amination of Unactivated Aryl Chlorides", J. Am. Chem. Soc., 120 (37): 9722–9723, doi:10.1021/ja982250+
  • Wolfe, J.P.; Buchwald, S.L. (1999), "A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides", Angew. Chem. Int. Ed., 38 (16): 2413–2416, doi:10.1002/(sici)1521-3773(19990816)38:16<2413::aid-anie2413>3.0.co;2-h, PMID 10458806
  • Hamann, B.C.; Hartwig, J.F. (1998), "Sterically Hindered Chelating Alkyl Phosphines Provide Large Rate Accelerations in Palladium-Catalyzed Amination of Aryl Iodides, Bromides, and Chlorides, and the First Amination of Aryl Tosylates", J. Am. Chem. Soc., 120 (29): 7369–7370, doi:10.1021/ja981318i
  • Wolfe, J.P.; Tomori, H.; Sadighi, J.P.; Yin, J.; Buchwald, S.L. (2000), "Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates" (PDF), J. Org. Chem., 65 (4): 1158–1174, doi:10.1021/jo991699y, PMID 10814067
  • Stambuli, J.P.; Kuwano, R.; Hartwig, J.F. (2002), "Unparalleled Rates for the Activation of Aryl Chlorides and Bromides: Coupling with Amines and Boronic Acids in Minutes at Room Temperature", Angew. Chem. Int. Ed., 41 (24): 4746–4748, doi:10.1002/anie.200290036, PMID 12481346
  • Huang, X.; Anderson, K.W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S.L. (2003), "Expanding Pd-Catalyzed C–N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions", J. Am. Chem. Soc., 125 (22): 6653–6655, doi:10.1021/ja035483w, PMID 12769573
  • Anderson, K.W.; Tundel, R.E.; Ikawa, T.; Altman, R.A.; Buchwald, S.L. (2006), "Monodentate Phosphines Provide Highly Active Catalysts for Pd-Catalyzed C–N Bond-Forming Reactions of Heteroaromatic Halides/Amines and (H)N-Heterocycles", Angew. Chem. Int. Ed., 45 (39): 6523–6527, doi:10.1002/anie.200601612, PMID 16955526
  • Ikawa, T.; Barder, T.E.; Biscoe, M.R.; Buchwald, S.L. (2007), "Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands: A Kinetic, Computational, and Synthetic Investigation", J. Am. Chem. Soc., 129 (43): 13001–13007, doi:10.1021/ja0717414, PMID 17918833
  • Wolfe, J.P.; Ahman, J.; Sadighi, J.P.; Singer, R.A.; Buchwald, S.L. (1997), "An Ammonia Equivalent for the Palladium-Catalyzed Amination of Aryl Halides and Triflates", Tetrahedron Lett., 38 (36): 6367–6370, doi:10.1016/S0040-4039(97)01465-2
  • Lee, S.; Jorgensen, M.; Hartwig, J.F. (2001), "Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides and Lithium Bis(trimethylsilyl)amide as an Ammonia Equivalent", Org. Lett., 3 (17): 2729–2732, doi:10.1021/ol016333y, PMID 11506620
  • Huang, X.; Buchwald, S.L. (2001), "New Ammonia Equivalents for the Pd-Catalyzed Amination of Aryl Halides", Org. Lett., 3 (21): 3417–3419, doi:10.1021/ol0166808, PMID 11594848
  • Vo, G.D.; Hartwig, J.F. (2009), "Palladium-Catalyzed Coupling of Ammonia with Aryl Chlorides, Bromides, Iodides, and Sulfonates: A General Method for the Preparation of Primary Arylamines", J. Am. Chem. Soc., 131 (31): 11049–11061, doi:10.1021/ja903049z, PMC 2823124, PMID 19591470
  • Mann, G.; Incarvito, C.; Rheingold, A.L.; Hartwig, J.F. (1999), "Palladium-Catalyzed C–O Coupling Involving Unactivated Aryl Halides. Sterically Induced Reductive Elimination To Form the C–O Bond in Diaryl Ethers", J. Am. Chem. Soc., 121: 3224–3225, doi:10.1021/ja984321a
  • Torraca, K.E.; Huang, X.; Parrish, C.A.; Buchwald, S.L. (2001), "An Efficient Intermolecular Palladium-Catalyzed Synthesis of Aryl Ethers", J. Am. Chem. Soc., 123 (43): 10770–10771, doi:10.1021/ja016863p, PMID 11674023
  • Heesgaard Jepsen Tue (2011). "Synthesis of Functionalized Dibenzothiophenes - An Efficient Three-Step Approach Based on Pd-Catalyzed C–C and CS Bond Formations". European Journal of Organic Chemistry. 2011: 53–57. doi:10.1002/ejoc.201001393.
  • Culkin, D.A.; Hartwig, J.F. (2003), "Palladium-Catalyzed r-Arylation of Carbonyl Compounds and Nitriles", Acc. Chem. Res., 36 (4): 234–245, doi:10.1021/ar0201106, PMID 12693921
  • Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S.L. (2002), "An Improved Catalyst for the Asymmetric Arylation of Ketone Enolates", J. Am. Chem. Soc., 124 (7): 1261–1268, doi:10.1021/ja011122+, PMID 11841295
  • Liao, X.; Weng, Z.; Hartwig, J.F. (2008), "Enantioselective r-Arylation of Ketones with Aryl Triflates Catalyzed by Difluorphos Complexes of Palladium and Nickel", J. Am. Chem. Soc., 130 (1): 195–200, doi:10.1021/ja074453g, PMC 2551326, PMID 18076166

matthey.com

technology.matthey.com

nih.gov

pubmed.ncbi.nlm.nih.gov

  • Hartwig, J.F. (1998), "Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism", Angew. Chem. Int. Ed., 37 (15): 2046–2067, doi:10.1002/(sici)1521-3773(19980817)37:15<2046::aid-anie2046>3.0.co;2-l, PMID 29711045
  • Hartwig, J.F. (2008), "Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides", Acc. Chem. Res., 41 (11): 1534–1544, doi:10.1021/ar800098p, PMC 2819174, PMID 18681463
  • Surry, D.S.; Buchwald, S.L. (2008), "Biaryl Phosphane Ligands in Palladium-Catalyzed Amination", Angew. Chem. Int. Ed., 47 (34): 6338–6361, doi:10.1002/anie.200800497, PMC 3517088, PMID 18663711
  • Surry, D.S.; Buchwald, S.L. (2011), "Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide", Chem. Sci., 2 (1): 27–50, doi:10.1039/c0sc00331j, PMC 3306613, PMID 22432049
  • Wolfe, J.P.; Buchwald, S.L. (1999), "A Highly Active Catalyst for the Room-Temperature Amination and Suzuki Coupling of Aryl Chlorides", Angew. Chem. Int. Ed., 38 (16): 2413–2416, doi:10.1002/(sici)1521-3773(19990816)38:16<2413::aid-anie2413>3.0.co;2-h, PMID 10458806
  • Wolfe, J.P.; Tomori, H.; Sadighi, J.P.; Yin, J.; Buchwald, S.L. (2000), "Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates" (PDF), J. Org. Chem., 65 (4): 1158–1174, doi:10.1021/jo991699y, PMID 10814067
  • Stambuli, J.P.; Kuwano, R.; Hartwig, J.F. (2002), "Unparalleled Rates for the Activation of Aryl Chlorides and Bromides: Coupling with Amines and Boronic Acids in Minutes at Room Temperature", Angew. Chem. Int. Ed., 41 (24): 4746–4748, doi:10.1002/anie.200290036, PMID 12481346
  • Huang, X.; Anderson, K.W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S.L. (2003), "Expanding Pd-Catalyzed C–N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed Reactions", J. Am. Chem. Soc., 125 (22): 6653–6655, doi:10.1021/ja035483w, PMID 12769573
  • Anderson, K.W.; Tundel, R.E.; Ikawa, T.; Altman, R.A.; Buchwald, S.L. (2006), "Monodentate Phosphines Provide Highly Active Catalysts for Pd-Catalyzed C–N Bond-Forming Reactions of Heteroaromatic Halides/Amines and (H)N-Heterocycles", Angew. Chem. Int. Ed., 45 (39): 6523–6527, doi:10.1002/anie.200601612, PMID 16955526
  • Ikawa, T.; Barder, T.E.; Biscoe, M.R.; Buchwald, S.L. (2007), "Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands: A Kinetic, Computational, and Synthetic Investigation", J. Am. Chem. Soc., 129 (43): 13001–13007, doi:10.1021/ja0717414, PMID 17918833
  • Lee, S.; Jorgensen, M.; Hartwig, J.F. (2001), "Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides and Lithium Bis(trimethylsilyl)amide as an Ammonia Equivalent", Org. Lett., 3 (17): 2729–2732, doi:10.1021/ol016333y, PMID 11506620
  • Huang, X.; Buchwald, S.L. (2001), "New Ammonia Equivalents for the Pd-Catalyzed Amination of Aryl Halides", Org. Lett., 3 (21): 3417–3419, doi:10.1021/ol0166808, PMID 11594848
  • Vo, G.D.; Hartwig, J.F. (2009), "Palladium-Catalyzed Coupling of Ammonia with Aryl Chlorides, Bromides, Iodides, and Sulfonates: A General Method for the Preparation of Primary Arylamines", J. Am. Chem. Soc., 131 (31): 11049–11061, doi:10.1021/ja903049z, PMC 2823124, PMID 19591470
  • Torraca, K.E.; Huang, X.; Parrish, C.A.; Buchwald, S.L. (2001), "An Efficient Intermolecular Palladium-Catalyzed Synthesis of Aryl Ethers", J. Am. Chem. Soc., 123 (43): 10770–10771, doi:10.1021/ja016863p, PMID 11674023
  • Culkin, D.A.; Hartwig, J.F. (2003), "Palladium-Catalyzed r-Arylation of Carbonyl Compounds and Nitriles", Acc. Chem. Res., 36 (4): 234–245, doi:10.1021/ar0201106, PMID 12693921
  • Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S.L. (2002), "An Improved Catalyst for the Asymmetric Arylation of Ketone Enolates", J. Am. Chem. Soc., 124 (7): 1261–1268, doi:10.1021/ja011122+, PMID 11841295
  • Liao, X.; Weng, Z.; Hartwig, J.F. (2008), "Enantioselective r-Arylation of Ketones with Aryl Triflates Catalyzed by Difluorphos Complexes of Palladium and Nickel", J. Am. Chem. Soc., 130 (1): 195–200, doi:10.1021/ja074453g, PMC 2551326, PMID 18076166

ncbi.nlm.nih.gov

  • Hartwig, J.F. (2008), "Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides", Acc. Chem. Res., 41 (11): 1534–1544, doi:10.1021/ar800098p, PMC 2819174, PMID 18681463
  • Surry, D.S.; Buchwald, S.L. (2008), "Biaryl Phosphane Ligands in Palladium-Catalyzed Amination", Angew. Chem. Int. Ed., 47 (34): 6338–6361, doi:10.1002/anie.200800497, PMC 3517088, PMID 18663711
  • Surry, D.S.; Buchwald, S.L. (2011), "Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide", Chem. Sci., 2 (1): 27–50, doi:10.1039/c0sc00331j, PMC 3306613, PMID 22432049
  • Vo, G.D.; Hartwig, J.F. (2009), "Palladium-Catalyzed Coupling of Ammonia with Aryl Chlorides, Bromides, Iodides, and Sulfonates: A General Method for the Preparation of Primary Arylamines", J. Am. Chem. Soc., 131 (31): 11049–11061, doi:10.1021/ja903049z, PMC 2823124, PMID 19591470
  • Liao, X.; Weng, Z.; Hartwig, J.F. (2008), "Enantioselective r-Arylation of Ketones with Aryl Triflates Catalyzed by Difluorphos Complexes of Palladium and Nickel", J. Am. Chem. Soc., 130 (1): 195–200, doi:10.1021/ja074453g, PMC 2551326, PMID 18076166

semanticscholar.org

api.semanticscholar.org

  • Forero-Cortés, Paola A.; Haydl, Alexander M. (2 July 2019). "The 25th Anniversary of the Buchwald–Hartwig Amination: Development, Applications, and Outlook". Organic Process Research & Development. 23 (8): 1478–1483. doi:10.1021/acs.oprd.9b00161. S2CID 198366762.
  • Hartwig, J.F. (1999), "Approaches to catalyst discovery. New carbon-heteroatom and carbon-carbon bond formation", Pure Appl. Chem., 71 (8): 1416–1423, doi:10.1351/pac199971081417, S2CID 34700080
  • Hartwig, J.F. (1997), "Palladium-Catalyzed Amination of Aryl Halides: Mechanism and Rational Catalyst Design", Synlett, 1997 (4): 329–340, doi:10.1055/s-1997-789, S2CID 196704196

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