메뉴 건너뛰기




Volumn 47, Issue 38, 2008, Pages 7230-7233

Palladium-catalyzed oxidative cyclization of N-aryl enamines: From anilines to indoles

Author keywords

C H activation; Heterocycles; Indoles; Oxidation; Palladium

Indexed keywords

AMINES; CHEMICAL REACTIONS; DIFFERENCE EQUATIONS; MATHEMATICAL TRANSFORMATIONS; PALLADIUM;

EID: 53249142637     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802482     Document Type: Article
Times cited : (420)

References (88)
  • 3
    • 29244491409 scopus 로고    scopus 로고
    • for the physiological activity of indole derivatives
    • c) T. Kawasaki, K. Higuchi, Nat. Prod. Rep. 2005, 22, 761; for the physiological activity of indole derivatives,
    • (2005) Nat. Prod. Rep , vol.22 , pp. 761
    • Kawasaki, T.1    Higuchi, K.2
  • 9
    • 22944454156 scopus 로고    scopus 로고
    • For reviews on methods for the synthesis of indoles, see: a
    • For reviews on methods for the synthesis of indoles, see: a) S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873;
    • (2005) Chem. Rev , vol.105 , pp. 2873
    • Cacchi, S.1    Fabrizi, G.2
  • 11
    • 4444376920 scopus 로고    scopus 로고
    • see also the following reviews: c
    • see also the following reviews: c) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079;
    • (2004) Chem. Rev , vol.104 , pp. 3079
    • Alonso, F.1    Beletskaya, I.P.2    Yus, M.3
  • 13
    • 53249085567 scopus 로고    scopus 로고
    • for some recent indole syntheses, see: e
    • for some recent indole syntheses, see: e) M. Shen, B. E. Leslie, T. G. Driver, Angew. Chem. 2008, 120, 5134;
    • (2008) Angew. Chem , vol.120 , pp. 5134
    • Shen, M.1    Leslie, B.E.2    Driver, T.G.3
  • 24
    • 53249155699 scopus 로고    scopus 로고
    • For the use of indole derivatives in cross-dehydrogenative coupling (CDC) reactions, see: a) T. Tsuchimoto, Y. Ozawa, R. Negoro, E. Shirakawa, Y. Kawakami, Angew. Chem. 2004, 116, 4327;
    • For the use of indole derivatives in cross-dehydrogenative coupling (CDC) reactions, see: a) T. Tsuchimoto, Y. Ozawa, R. Negoro, E. Shirakawa, Y. Kawakami, Angew. Chem. 2004, 116, 4327;
  • 29
    • 34249936878 scopus 로고    scopus 로고
    • for a remarkable CDC of indoles with unfunctionalized benzene derivatives, see: e D. R. Stuart, K. Fagnou, Science 2007, 316, 1172;
    • for a remarkable CDC of indoles with unfunctionalized benzene derivatives, see: e) D. R. Stuart, K. Fagnou, Science 2007, 316, 1172;
  • 44
    • 20544450502 scopus 로고    scopus 로고
    • 2nd ed, Eds, A. de Meijere, F. Diederich, Wiley-VCH, Weinheim
    • b) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
    • (2004) Metal-Catalyzed Cross-Coupling Reactions
  • 58
    • 0001304357 scopus 로고    scopus 로고
    • For a palladium-catalyzed cyclization of a single N-aryl- substituted (cyclic) enaminone under neutral conditions in 31% yield, see: a) H. Iida, Y. Yuasa, C. Kibayashi, J. Org. Chem. 1980, 45, 2938;
    • For a palladium-catalyzed cyclization of a single N-aryl- substituted (cyclic) enaminone under neutral conditions in 31% yield, see: a) H. Iida, Y. Yuasa, C. Kibayashi, J. Org. Chem. 1980, 45, 2938;
  • 59
    • 0001196247 scopus 로고    scopus 로고
    • for a two-step synthesis of indoles by anodic oxidation of an enaminone in 35% yield, and additional cyclizations, see: b W. Eilenberg, H. J. Schäfer, Tetrahedron Lett. 1984, 25, 5023;
    • for a two-step synthesis of indoles by anodic oxidation of an enaminone in 35% yield, and additional cyclizations, see: b) W. Eilenberg, H. J. Schäfer, Tetrahedron Lett. 1984, 25, 5023;
  • 62
    • 53249107322 scopus 로고    scopus 로고
    • [5d]
    • [5d]
  • 63
    • 0035128727 scopus 로고    scopus 로고
    • For Suzuki-Miyaura reactions of chloroindoles, see: a
    • For Suzuki-Miyaura reactions of chloroindoles, see: a) A. FOrstner, A. Leitner, Synlett 2001, 290;
    • (2001) Synlett , pp. 290
    • FOrstner, A.1    Leitner, A.2
  • 66
    • 53249128629 scopus 로고    scopus 로고
    • Bromo-substituted indoles can also be formed; however, a significant amount of the debrominated indole product is also obtained. The optimization of this reaction will be described at a later stage
    • Bromo-substituted indoles can also be formed; however, a significant amount of the debrominated indole product is also obtained. The optimization of this reaction will be described at a later stage.
  • 67
    • 53249140072 scopus 로고    scopus 로고
    • As an example of the value of this method, we quote for one transformation the cost of purchasing the starting materials and the product in 99% purity from Sigma-Aldrich: aniline: 1 L/€24; ethyl acetoacetate: 1 kg/€37; ethyl-2-methylindole-3-carboxylate (2u): 1 g/€60.60.
    • As an example of the value of this method, we quote for one transformation the cost of purchasing the starting materials and the product in 99% purity from Sigma-Aldrich: aniline: 1 L/€24; ethyl acetoacetate: 1 kg/€37; ethyl-2-methylindole-3-carboxylate (2u): 1 g/€60.60.
  • 72
    • 53249089875 scopus 로고    scopus 로고
    • An initial olefin-palladium π complex should also be considered; see: F. Glorius, Angew. Chem. 2004, 116, 3444;
    • An initial olefin-palladium π complex should also be considered; see: F. Glorius, Angew. Chem. 2004, 116, 3444;
  • 73
    • 4544236676 scopus 로고    scopus 로고
    • and references therein
    • Angew. Chem. Int. Ed. 2004, 43, 3364, and references therein.
    • (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3364
  • 78
    • 0037771628 scopus 로고    scopus 로고
    • Some alternative, though less likely mechanisms, may be considered; for a Heck carbopalladation, see: a
    • Some alternative, though less likely mechanisms, may be considered; for a Heck carbopalladation, see: a) C. C. Hughes, D. Trauner, Angew. Chem. 2002, 114, 1639;
    • (2002) Angew. Chem , vol.114 , pp. 1639
    • Hughes, C.C.1    Trauner, D.2
  • 81
    • 18744368757 scopus 로고    scopus 로고
    • IV intermediate, see: c A. J. Mota, A. Dedieu, C. Bour, J. Suffert, J. Am. Chem. Soc. 2005, 127, 7171;
    • IV intermediate, see: c) A. J. Mota, A. Dedieu, C. Bour, J. Suffert, J. Am. Chem. Soc. 2005, 127, 7171;
  • 82
    • 53249134242 scopus 로고    scopus 로고
    • II species, see: d J. Cámpora, E. Gutiérrez-Puebla, J. A. López, A. Monge, P. Palma, D. del Río, E. Carmona, Angew. Chem. 2001, 113, 3753;
    • II species, see: d) J. Cámpora, E. Gutiérrez-Puebla, J. A. López, A. Monge, P. Palma, D. del Río, E. Carmona, Angew. Chem. 2001, 113, 3753;
  • 84
    • 53249153232 scopus 로고    scopus 로고
    • The following reactivity order was found for para-substituted aniline substrates: Cl > H ≈ Me > OMe. Details are provided in the Supporting Information.
    • The following reactivity order was found for para-substituted aniline substrates: Cl > H ≈ Me > OMe. Details are provided in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.