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Volumn 9, Issue 25, 2007, Pages 5255-5258

Synthesis of benzannulated N-heterocycles by a palladium-catalyzed C-C/C-N coupling of bromoalkylamines

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BENZENE; BROMINE DERIVATIVE; CARBON; HETEROCYCLIC COMPOUND; HYDROQUINONE; HYDROQUINONE DERIVATIVE; INDOLE DERIVATIVE; NITROGEN; PALLADIUM;

EID: 37249017443     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702472u     Document Type: Article
Times cited : (99)

References (45)
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    • For 5-hydroxytryptamine receptor antagonists, see: (a) Bermudez, J.; Dabbs, S.; Joiner, K. A.; King, F. D. J. Med. Chem. 1990, 33, 1929.
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    • For examples, see: a
    • For examples, see: (a) Lira, R.; Wolfe, J. P. J. Am. Chem. Soc. 2004, 126, 13906.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 13906
    • Lira, R.1    Wolfe, J.P.2
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    • For the synthesis of indoles and indolines that are highly substituted on the benzenoid ring, see
    • For the synthesis of indoles and indolines that are highly substituted on the benzenoid ring, see: Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 5776
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    • For selected examples with the Heck reaction, see: a
    • For selected examples with the Heck reaction, see: (a) Piguel, S.; Lautens, M. Angew. Chem., Int. Ed. 2000, 39, 1045.
    • (2000) Angew. Chem., Int. Ed , vol.39 , pp. 1045
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    • With direct arylation, see: (e) Bressy, C, Alberico, D, Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148
    • With direct arylation, see: (e) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148.
  • 28
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    • Catellani has reported a domino ortho-arylation/amidation reaction: Ferraccioli, R.; Carenzi, D.; Rombolà, O.; Catellani, M. Org. Lett. 2004, 6, 4759.
    • Catellani has reported a domino ortho-arylation/amidation reaction: Ferraccioli, R.; Carenzi, D.; Rombolà, O.; Catellani, M. Org. Lett. 2004, 6, 4759.
  • 29
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    • 2 with aryl halides, see: (a) Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 10028.
    • 2 with aryl halides, see: (a) Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 10028.
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    • For the coupling of silyl-protected arenethiols with aryl halides, see: c
    • For the coupling of silyl-protected arenethiols with aryl halides, see: (c) Kreis, M.; Bräse, S. Adv. Synth. Catal. 2005, 47, 313.
    • (2005) Adv. Synth. Catal , vol.47 , pp. 313
    • Kreis, M.1    Bräse, S.2
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    • For examples, see: (a) Ref 7b.
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  • 39
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    • Catellani reported that isopropyl iodide could be used in the ortho-alkylation/vinylation reaction with 31% conversion using a large excess of the halide: Catellani, M.; Cugini, F. Tetrahedron 1999, 55, 6595.
    • Catellani reported that isopropyl iodide could be used in the ortho-alkylation/vinylation reaction with 31% conversion using a large excess of the halide: Catellani, M.; Cugini, F. Tetrahedron 1999, 55, 6595.
  • 40
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    • Preliminary results show that reaction with 3-nitro-2-methyliodobenzene produces the indole in 27% unoptimized yield
    • Preliminary results show that reaction with 3-nitro-2-methyliodobenzene produces the indole in 27% unoptimized yield.
  • 44
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    • 2Et-protected amine gave no products.
    • 2Et-protected amine gave no products.
  • 45
    • 37249002545 scopus 로고    scopus 로고
    • Based on the mechanistic proposal of Catellani and co-workers, see ref 13 and references therein
    • Based on the mechanistic proposal of Catellani and co-workers, see ref 13 and references therein.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.