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Volumn 17, Issue 36, 2011, Pages 10113-10122

Nickel-catalyzed C-H arylation of azoles with haloarenes: Scope, mechanism, and applications to the synthesis of bioactive molecules

Author keywords

C H functionalization; cross coupling; drug discovery; heterocycles; natural products; nickel

Indexed keywords

C-H FUNCTIONALIZATION; CROSS-COUPLINGS; DRUG DISCOVERY; HETEROCYCLES; NATURAL PRODUCTS;

EID: 80052020935     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101091     Document Type: Article
Times cited : (182)

References (125)
  • 1
    • 80051992536 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 3
    • 22744442306 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4442-4489
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 4442-4489
  • 5
    • 20544450502 scopus 로고    scopus 로고
    • 2 nd ed. (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim
    • Metal-Catalyzed Cross-coupling Reactions, 2 nd ed., (Eds.: A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, 2004
    • (2004) Metal-Catalyzed Cross-coupling Reactions
  • 7
    • 80051986054 scopus 로고    scopus 로고
    • For selected reviews on catalytic C-H bond arylation of arenes, see
    • For selected reviews on catalytic C-H bond arylation of arenes, see
  • 16
    • 84891012324 scopus 로고    scopus 로고
    • in (Ed.: L. Ackermann), Wiley-VCH, Weinheim
    • M. Miura, T. Satoh, in Modern Arylation Methods (Ed.:, L. Ackermann,), Wiley-VCH, Weinheim, 2009, pp. 335-361
    • (2009) Modern Arylation Methods , pp. 335-361
    • Miura, M.1    Satoh, T.2
  • 18
    • 67649488045 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 5094-5115
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5094-5115
  • 20
    • 72449170089 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 9792-9826.
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 9792-9826
  • 21
    • 80051962356 scopus 로고    scopus 로고
    • For our recent achievements on this field, see
    • For our recent achievements on this field, see
  • 28
    • 70349915658 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2009, 48, 3644-3647
    • (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 3644-3647
  • 32
    • 78449231481 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 8946-8949
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 8946-8949
  • 34
    • 79952050537 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2011, 50, 2387-2391
    • (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 2387-2391
  • 37
    • 80051969983 scopus 로고    scopus 로고
    • For the synthesis of febuxostat, see
    • For the synthesis of febuxostat, see
  • 42
    • 10744228786 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 2758-2761.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 2758-2761
  • 43
    • 80051963033 scopus 로고    scopus 로고
    • For isolation and biological activity of muscoride A, see
    • For isolation and biological activity of muscoride A, see
  • 48
    • 0037471240 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 1411-1414.
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 1411-1414
  • 49
    • 80051977108 scopus 로고    scopus 로고
    • For isolation and biological activities of hennoxazole A, see
    • For isolation and biological activities of hennoxazole A, see
  • 57
    • 80051972601 scopus 로고    scopus 로고
    • For biological activities and synthesis, see
    • For biological activities and synthesis, see
  • 60
    • 80051972088 scopus 로고    scopus 로고
    • For the isolation and biological activities of GE2270A, see
    • For the isolation and biological activities of GE2270A, see
  • 64
    • 33845290273 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 7786-7792
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7786-7792
  • 66
    • 34347213763 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 4771-4774
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 4771-4774
  • 68
    • 80051963820 scopus 로고    scopus 로고
    • For biological activities, see
    • For biological activities, see
  • 73
    • 80051995005 scopus 로고    scopus 로고
    • For the isolation of texaline and texamine, see
    • For the isolation of texaline and texamine, see
  • 79
    • 80051993621 scopus 로고    scopus 로고
    • For selected examples of the synthesis of 2-arylated azoles by Pd-catalyzed direct arylation of azoles, see
    • For selected examples of the synthesis of 2-arylated azoles by Pd-catalyzed direct arylation of azoles, see
  • 85
    • 35648969183 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 7996-8000
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 7996-8000
  • 99
    • 77949371749 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2010, 49, 2202-2205.
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2202-2205
  • 100
    • 80051967253 scopus 로고    scopus 로고
    • For selected recent examples of Ni-catalyzed C-H functionalization, see
    • For selected recent examples of Ni-catalyzed C-H functionalization, see
  • 108
    • 84855744618 scopus 로고    scopus 로고
    • 2O was used without pretreatment, 3 Aa was obtained in 23 % yield.
    • 2O was used without pretreatment, 3 Aa was obtained in 23 % yield.
  • 109
    • 80051991824 scopus 로고    scopus 로고
    • Higher reactivity of ortho-substituted halobenzenes might be ascribed to steric-induced acceleration in the product-forming reductive elimination step in the catalytic cycle (Scheme 2).
    • Higher reactivity of ortho-substituted halobenzenes might be ascribed to steric-induced acceleration in the product-forming reductive elimination step in the catalytic cycle (Scheme 2).
  • 110
    • 80052011373 scopus 로고    scopus 로고
    • Miura and co-workers also indicated such a phenomenon; see reference [18].
    • Miura and co-workers also indicated such a phenomenon; see reference [18].
  • 111
    • 80051971062 scopus 로고    scopus 로고
    • See the Supporting Information for further details.
    • See the Supporting Information for further details.
  • 117
    • 80051983883 scopus 로고    scopus 로고
    • For successful and unsuccessful examples of organolithium cross-coupling, see
    • For successful and unsuccessful examples of organolithium cross-coupling, see
  • 125
    • 84855746744 scopus 로고    scopus 로고
    • 2 ($610 for 2 g).
    • 2 ($610 for 2 g).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.