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Volumn 105, Issue 7, 2005, Pages 2873-2920

Synthesis and functionalization of indoles through palladium-catalyzed reactions

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CATALYSTS; CHEMICAL BONDS; COMPLEXATION; MOLECULAR DYNAMICS; NITROGEN COMPOUNDS; OLEFINS; ORGANOMETALLICS; PALLADIUM COMPOUNDS; REDUCTION; SYNTHESIS (CHEMICAL);

EID: 22944454156     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr040639b     Document Type: Review
Times cited : (1742)

References (435)
  • 1
    • 84943388739 scopus 로고
    • Katritzky, A. R., Rees, C.W., Eds.; Pergamon: Oxford
    • Sundberg R. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4, p 313.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 313
    • Sundberg, R.J.1
  • 2
    • 22944493132 scopus 로고
    • For some recent books on palladium catalysis in organic synthesis, see: Liebeskind, L. S., Ed.; JAI Press: London, Chapter 3
    • For some recent books on palladium catalysis in organic synthesis, see: Larock, R. C. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1994; Vol. 5, Chapter 3.
    • (1994) Advances in Metal-Organic Chemistry , vol.5
    • Larock, R.C.1
  • 7
    • 0034249671 scopus 로고    scopus 로고
    • For some masterful recent reviews on palladium catalysis in organic synthesis, see: Heck reaction:
    • For some masterful recent reviews on palladium catalysis in organic synthesis, see: Heck reaction: Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
    • (2000) Chem. Rev. , vol.100 , pp. 3009
    • Beletskaya, I.P.1    Cheprakov, A.V.2
  • 11
    • 0013165218 scopus 로고    scopus 로고
    • Special Issue 30 Years of the Cross-coupling Reaction
    • Special Issue 30 Years of the Cross-coupling Reaction. J. Organomet. Chem. 2002, 653, 1.
    • (2002) J. Organomet. Chem. , vol.653 , pp. 1
  • 12
    • 0036589259 scopus 로고    scopus 로고
    • Reactions of aryl halides with soft nonorganometallic nucleophiles:
    • Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. Reactions of aryl halides with soft, nonorganometallic nucleophiles:
    • (2002) Chem. Rev. , vol.102 , pp. 1359
    • Hassan, J.1    Sevignon, M.2    Gozzi, C.3    Schulz, E.4    Lemaire, M.5
  • 15
    • 0037943974 scopus 로고    scopus 로고
    • Synthesis of nucleosides:
    • Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979. Synthesis of nucleosides:
    • (2003) Chem. Rev. , vol.103 , pp. 1979
    • Negishi, E.1    Anastasia, L.2
  • 16
    • 0037944068 scopus 로고    scopus 로고
    • Synthesis and reactions of organometallic reagents:
    • Agrofoglio, L. A.; Gillalzeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875. Synthesis and reactions of organometallic reagents:
    • (2003) Chem. Rev. , vol.103 , pp. 1875
    • Agrofoglio, L.A.1    Gillalzeau, I.2    Saito, Y.3
  • 19
    • 0038106766 scopus 로고    scopus 로고
    • Removing palladium impurities from organic compounds of pharmaceutical interest:
    • Muzart, J. Tetrahedron 2003, 59, 5789. Removing palladium impurities from organic compounds of pharmaceutical interest:
    • (2003) Tetrahedron , vol.59 , pp. 5789
    • Muzart, J.1
  • 22
    • 0001591528 scopus 로고    scopus 로고
    • For some major review articles on palladium catalysis in the synthesis and functionalization of heterocycles, see:
    • For some major review articles on palladium catalysis in the synthesis and functionalization of heterocycles, see: Li, J. J. Alkaloids: Chemical and Biological Perspectives 1999, 14, 437.
    • (1999) Alkaloids: Chemical and Biological Perspectives , vol.14 , pp. 437
    • Li, J.J.1
  • 46
    • 0346602829 scopus 로고
    • For some reviews on allylic alkylations, see:
    • For some reviews on allylic alkylations, see: Tsuji, J. Tetrahedron 1986, 42, 4361.
    • (1986) Tetrahedron , vol.42 , pp. 4361
    • Tsuji, J.1
  • 60
    • 0037016413 scopus 로고    scopus 로고
    • For a recent review on halide effects in transition metal catalysis, see:
    • For a recent review on halide effects in transition metal catalysis, see: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 26
    • Fagnou, K.1    Lautens, M.2
  • 63
    • 22944432675 scopus 로고    scopus 로고
    • For a review, see ref 3a
    • For a review, see ref 3a.
  • 101
    • 1842740801 scopus 로고    scopus 로고
    • aryl-N bond, see:
    • aryl-N bond, see: Hartwig, J. F. Synlett 1997, 329.
    • (1997) Synlett , pp. 329
    • Hartwig, J.F.1
  • 116
    • 0002769275 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-WCH: Weinheim, Germany
    • Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-WCH: Weinheim, Germany, 1998; p 203.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 203
    • Sonogashira, K.1
  • 117
    • 0001545058 scopus 로고
    • For the coupling of terminal alkynes with aryl halides without the use of Cu salts, see:
    • For the coupling of terminal alkynes with aryl halides without the use of Cu salts, see: Cassar, L. J. Organomet. Chem. 1975, 93, 253.
    • (1975) J. Organomet. Chem. , vol.93 , pp. 253
    • Cassar, L.1
  • 119
    • 0028829217 scopus 로고
    • For copper-assisted syntheses ofindoles from o-alkynylanilines -anilides, see:
    • For copper-assisted syntheses ofindoles from o-alkynylanilines and -anilides, see: Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 7841
    • Saulnier, M.G.1    Frennesson, D.B.2    Deshpande, M.S.3    Vyas, D.M.4
  • 121
    • 0037060012 scopus 로고    scopus 로고
    • For copper-catalyzed cyclizations of o-alkynylanilides and -anilines to indoles, see:
    • For copper-catalyzed cyclizations of o-alkynylanilides and -anilines to indoles, see: Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1277
    • Hiroya, K.1    Itoh, S.2    Ozawa, M.3    Kanamori, Y.4    Sakamoto, T.5
  • 124
    • 22944492545 scopus 로고
    • For some leading references on basic cyclization of o-alkynylanilines and o-alkynylanilides, see:
    • For some leading references on basic cyclization of o -alkynylanilines and o-alkynylanilides, see: Shin, K.; Ogasawara, K. Chem. Lett. 1995, 289.
    • (1995) Chem. Lett. , vol.289
    • Shin, K.1    Ogasawara, K.2
  • 161
    • 0036628561 scopus 로고    scopus 로고
    • For a review on traceless solid-phase organic synthesis, see:
    • For a review on traceless solid-phase organic synthesis, see: Blaney, P.; Grigg, R.; Sridharan, V. Chem. Rev. 2002, 102, 2607.
    • (2002) Chem. Rev. , vol.102 , pp. 2607
    • Blaney, P.1    Grigg, R.2    Sridharan, V.3
  • 172
    • 0037583537 scopus 로고    scopus 로고
    • For recent references on the activation of carbon - Carbon triple bonds by organopalladium complexes toward nucleophilic attack by proximate nucleophiles, see: oxygen nucleophiles: Negishi, E., Ed.; John Wiley & Sons: New York
    • For recent references on the activation of carbon - carbon triple bonds by organopalladium complexes toward nucleophilic attack by proximate nucleophiles, see: oxygen nucleophiles: Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002; p 2193.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , pp. 2193
    • Cacchi, S.1    Arcadi, A.2
  • 227
    • 0002524474 scopus 로고
    • For a review, see:
    • For a review, see: Trost, B. M. Acc.Chem. Res. 1990, 23, 34.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 34
    • Trost, B.M.1
  • 268
    • 0141765945 scopus 로고    scopus 로고
    • See also:
    • Ma, S. Acc. Chem. Res. 2003, 36, 701. See also:
    • (2003) Acc. Chem. Res. , vol.36 , pp. 701
    • Ma, S.1
  • 281
    • 37049089174 scopus 로고
    • For some examples of synthetic approaches to o-vinylanilines, see: elimination of(aminophenyl)ethanol derivatives: Wittig reaction:
    • For some examples of synthetic approaches to o-vinylanilines, see: elimination of(aminophenyl)ethanol derivatives: Sato, T.; Ishida, S.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1991, 353. Wittig reaction:
    • (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 353
    • Sato, T.1    Ishida, S.2    Ishibashi, H.3    Ikeda, M.4
  • 282
    • 0000753518 scopus 로고
    • Synthesis of o-nitrostyrenes followed by reduction:
    • Hibino, S.; Sugino, E. Heterocycles 1987, 26, 1883. Synthesis of o-nitrostyrenes followed by reduction:
    • (1987) Heterocycles , vol.26 , pp. 1883
    • Hibino, S.1    Sugino, E.2
  • 285
    • 0000308248 scopus 로고
    • Stille reaction Reference 133d
    • Plevyak, J. E.; Heck, R. F. J. Org. Chem. 1978, 43, 2454. Stille reaction: Reference 133d.
    • (1978) J. Org. Chem. , vol.43 , pp. 2454
    • Plevyak, J.E.1    Heck, R.F.2
  • 304
    • 0000540948 scopus 로고
    • For some examples of palladium-catalyzed overall trans additions to acetylenic compounds, see:
    • For some examples of palladium-catalyzed overall trans additions to acetylenic compounds, see: Zargarian, D.; Alper, H. Organometallics 1991, 10, 2914.
    • (1991) Organometallics , vol.10 , pp. 2914
    • Zargarian, D.1    Alper, H.2
  • 317
    • 22944437252 scopus 로고    scopus 로고
    • For a mechanistic rationale for regioselectivity of the direct palladium-catalyzed C-2 and C-3 arylation of indoles, see: in press
    • For a mechanistic rationale for regioselectivity of the direct palladium-catalyzed C-2 and C-3 arylation of indoles, see: Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc., in press.
    • J. Am. Chem. Soc.
    • Lane, B.S.1    Brown, M.A.2    Sames, D.3
  • 335
    • 4644245555 scopus 로고    scopus 로고
    • For a recent review on the mechanisms of the Stille reaction, see:
    • For a recent review on the mechanisms of the Stille reaction, see: Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 4704
    • Espinet, P.1    Echavarren, A.M.2


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