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Volumn 124, Issue 39, 2002, Pages 11684-11688

The copper-catalyzed N-arylation of indoles

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATION;

EID: 0037009958     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja027433h     Document Type: Article
Times cited : (597)

References (45)
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    • note
    • We would like to thank Arran Chemical Company for a generous gift of ligand 1a.
  • 29
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    • note
    • Ligand screening has shown that N-aryl-1,2-diamines (mono or bis) are poor ligands for the N-arylation of indole.
  • 30
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    • note
    • While they are not recommended as a first choice, in some cases their use may be easier vis á vis long-term storage than for the free base.
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    • Massachusetts Institute of Technology. Unpublished results
    • Induction periods were observed and are currently being studied in similar amide arylation chemistry: Strieter, E. R.; Buchwald, S. L. Massachusetts Institute of Technology, 2002. Unpublished results.
    • (2002)
    • Strieter, E.R.1    Buchwald, S.L.2
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    • note
    • CuI (98% purity, purchased from Strem) was of a fine powdered quality.
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    • note
    • Tryptamine (entry 4), melatonin (entry 5), and 5-methoxytryptamine (entry 8) gave a single regioisomer by GC/MS of the crude reaction mixture. However, the reaction employing tryptophol (entry 6) as a substrate gave 7% of the respective bis-arylated byproduct (GC/MS).
  • 34
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    • Practical palladium catalysts for C-N and C-O bond formation
    • Miyaura, N., Ed.; Springer-Verlag: Berlin
    • For reviews on Pd-catalyzed amination, see (a) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p. 133. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576 (1-2), 125. For an example of a new copper-catalyzed amination method, see (e) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
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    • For reviews on Pd-catalyzed amination, see (a) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, p. 133. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576 (1-2), 125. For an example of a new copper-catalyzed amination method, see (e) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
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    • note
    • 3, DMF, 110 °C (63% conversion).
  • 40
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    • note
    • Following conditions of Table 5: Reaction of 2-methylindole with 2-bromotoluene gave no conversion. Reaction of 2-methylindole with 2-iodotoluene gave 10% conversion. Reaction of 2-methylindole with 2-bromoanisole gave only 47% conversion.
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    • note
    • 4 purchased from Alfa Aesar could be ground to a fine powder that provided reproducible results for the several reactions where it was used.
  • 45
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    • note
    • Dodecane was used in the above reactions as an internal GC standard.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.