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Volumn , Issue 11, 2004, Pages 1965-1969

Synthesis of 2-substituted indoles via Pd/C-catalyzed reaction in water

Author keywords

Indoles; Palladium catalyst; Sonogashira coupling 5 endo dig cyclization; Water

Indexed keywords

ALKYNE; ANILIDE; COPPER; ETHANOLAMINE; INDOLE; METHANOL DERIVATIVE; PALLADIUM; SOLVENT; WATER;

EID: 4544314128     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-830861     Document Type: Article
Times cited : (81)

References (76)
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    • For Cu-mediated process, see: (a) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843. (b) Ezquerra, J.; Pedregal, C.; Lamas, C.; Barluenga, J.; Perez, M.; Garcia-Martin, M. A.; Gonzalez, J. M. J. Org. Chem. 1996, 61, 5804. (c) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277.
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    • For Cu-mediated process, see: (a) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett. 2003, 5, 3843. (b) Ezquerra, J.; Pedregal, C.; Lamas, C.; Barluenga, J.; Perez, M.; Garcia-Martin, M. A.; Gonzalez, J. M. J. Org. Chem. 1996, 61, 5804. (c) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto, T. Tetrahedron Lett. 2002, 43, 1277.
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    • For Pd-mediated coupling reactions of haloindoles; see: (a) Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2000, 41, 8717. (b) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751.
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    • For Pd-mediated coupling reactions of haloindoles; see: (a) Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2000, 41, 8717. (b) Zhang, H.-C.; Ye, H.; White, K. B.; Maryanoff, B. E. Tetrahedron Lett. 2001, 42, 4751.
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    • note
    • (b) All the terminal alkynes used are commercially available.
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    • note
    • 3S requires C, 58.40; H, 6.41; N. 5.24%.
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    • Although the methanesulfonyl group of iodoarene 1e was tolerated under the present reaction conditions this group was removed efficiently from 4 using tetrabutylammonium fluoride in THF at elevated temperature to afford the corresponding indoles in good yields, see: Yasuhara, A.; Sakamoto, T. Tetrahedron Lett. 1998, 39, 595.
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    • 2 is thought to be the key intermediate and participates as active palladium species in these cross-coupling reactions, see: Grosshenny, V.; Romero, F. M.; Ziessel, R. J. Org. Chem. 1997, 62, 1491.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.