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Volumn 7, Issue 3, 2005, Pages 439-442

General and efficient indole syntheses based on catalytic amination reactions

Author keywords

[No Author keywords available]

Indexed keywords

CARBENOID; CHLOROBENZENE; COPPER; INDOLE; IODINE; NITROGEN; PALLADIUM COMPLEX;

EID: 13844272578     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047649j     Document Type: Article
Times cited : (204)

References (37)
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    • Selected recent examples: (b) Chen, C.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676-2677. (c) Nazaré, M.; Schneider, C.; Lindenschmidt, A.; Will, D. W. Angew. Chem., Int. Ed. 2004, 43, 4526-4528. (d) Ackermann, L.; Kaspar, L. T.; Gschrei, C. J. Chem. Commun. 2004, 2824-2825.
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    • Selected recent examples: (b) Chen, C.; Lieberman, D. R.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Org. Chem. 1997, 62, 2676-2677. (c) Nazaré, M.; Schneider, C.; Lindenschmidt, A.; Will, D. W. Angew. Chem., Int. Ed. 2004, 43, 4526-4528. (d) Ackermann, L.; Kaspar, L. T.; Gschrei, C. J. Chem. Commun. 2004, 2824-2825.
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    • For a two-step, one-pot approach consisting of a hydroamination and a subsequent intramolecular palladium-catalyzed amination reaction, see: Siebenreicher, H.; Bytschkov, I.; Doye, S. Angew. Chem., Int. Ed. 2003, 42, 3042-3044.
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    • For the use of heterocyclic carbene ligands in C-N bond-forming processes, see: (a) Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309. (b) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423-1426.
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    • note
    • 2O, 200/1) to yield 4a as a white solid (282 mg, 99%).
  • 27
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    • note
    • 4 led to complete conversion (4j: 40% isolated yield) and no conversion of the corresponding alkyne, respectively.
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    • note
    • 4 instead of KO-t-Bu under otherwise identical conditions to the one outlined in Table 1, entry 8, yielded exclusively the corresponding amine 3, supporting the sequence outlined in Scheme 1.
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    • note
    • 2O, 200/1 → 50/1) to yield 4n as a yellow oil (195 mg, 67%).
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    • KO-t-Bu can assist similar cyclization reactions via formation of an aryne intermediate. See, for example: Beller, M.; Breindl, C.; Riermeier, T. H.; Tillack, A. J. Org. Chem. 2001, 66, 1403-1412.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.