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Volumn 125, Issue 22, 2003, Pages 6653-6655

Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONIC ACID DERIVATIVE; CARBON; COPPER; NITROGEN; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONIC ACID DERIVATIVE;

EID: 0038579438     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035483w     Document Type: Article
Times cited : (748)

References (23)
  • 4
    • 0011411784 scopus 로고    scopus 로고
    • 2 could offer a partial solution to this problem, this was both experimentally complicated and still had a fairly narrow substrate scope (e.g., no primary aliphatic amines, no acyclic secondary amines): Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885.
    • (2002) Org. Lett. , vol.4 , pp. 2885
    • Harris, M.C.1    Huang, X.2    Buchwald, S.L.3
  • 6
    • 0032578172 scopus 로고    scopus 로고
    • (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (b) Hartwig, J. F.; Hamann, B. C. U.S. Patent 6,235,938, 2001. Ni-catalyzed coupling of sulfoximines with aryl tosylates: (c) Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000, 911.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7369
    • Hamann, B.C.1    Hartwig, J.F.2
  • 7
    • 0032578172 scopus 로고    scopus 로고
    • U.S. Patent 6,235,938, 2001
    • (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (b) Hartwig, J. F.; Hamann, B. C. U.S. Patent 6,235,938, 2001. Ni-catalyzed coupling of sulfoximines with aryl tosylates: (c) Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000, 911.
    • Hartwig, J.F.1    Hamann, B.C.2
  • 8
    • 0032578172 scopus 로고    scopus 로고
    • (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. (b) Hartwig, J. F.; Hamann, B. C. U.S. Patent 6,235,938, 2001. Ni-catalyzed coupling of sulfoximines with aryl tosylates: (c) Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000, 911.
    • (2000) Synthesis , vol.911
    • Bolm, C.1    Hildebrand, J.P.2    Rudolph, J.3
  • 9
    • 0011720666 scopus 로고    scopus 로고
    • Ligand 1 is commercially available from Strem Chemical. (a) Kaye, S.; Fox, J. M.; Hicks, F. A.; Buchwald, S. L. Adv. Synth. Catal. 2001, 343, 789. (b) Tomori, M.; Fox, J. M.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5334.
    • (2001) Adv. Synth. Catal. , vol.343 , pp. 789
    • Kaye, S.1    Fox, J.M.2    Hicks, F.A.3    Buchwald, S.L.4
  • 10
    • 0034714545 scopus 로고    scopus 로고
    • Ligand 1 is commercially available from Strem Chemical. (a) Kaye, S.; Fox, J. M.; Hicks, F. A.; Buchwald, S. L. Adv. Synth. Catal. 2001, 343, 789. (b) Tomori, M.; Fox, J. M.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5334.
    • (2000) J. Org. Chem. , vol.65 , pp. 5334
    • Tomori, M.1    Fox, J.M.2    Buchwald, S.L.3
  • 12
    • 0037140736 scopus 로고    scopus 로고
    • Only a few examples of the coupling of amides with aryl triflates have been disclosed, cf.: Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 6043
    • Yin, J.1    Buchwald, S.L.2
  • 14
    • 0038332036 scopus 로고    scopus 로고
    • note
    • In preliminary experiments, primary and secondary alcohols provided poor results while tert-amyl alcohol was a suitable solvent.
  • 19
    • 0037031625 scopus 로고    scopus 로고
    • Aqueous hydroxide as a base for palladium-catalyzed amination has been reported; however, a phase transfer catalyst and toluene cosolvent were required: (a) Kuwano, R.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2002, 67, 6479. For the use of solid NaOH in dioxane, see: (b) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729.
    • (2002) J. Org. Chem. , vol.67 , pp. 6479
    • Kuwano, R.1    Utsunomiya, M.2    Hartwig, J.F.3
  • 20
    • 0035900483 scopus 로고    scopus 로고
    • Aqueous hydroxide as a base for palladium-catalyzed amination has been reported; however, a phase transfer catalyst and toluene cosolvent were required: (a) Kuwano, R.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2002, 67, 6479. For the use of solid NaOH in dioxane, see: (b) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729.
    • (2001) J. Org. Chem. , vol.66 , pp. 7729
    • Grasa, G.A.1    Viciu, M.S.2    Huang, J.3    Nolan, S.P.4
  • 21
    • 0032510005 scopus 로고    scopus 로고
    • - could be used instead of 1 with comparable results. (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (b) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 617
    • Nishiyama, M.1    Yamamoto, T.2    Koie, Y.3
  • 22
    • 0035961019 scopus 로고    scopus 로고
    • - could be used instead of 1 with comparable results. (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617. (b) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
    • (2001) Org. Lett. , vol.3 , pp. 4295
    • Netherton, M.R.1    Fu, G.C.2


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