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Volumn 129, Issue 25, 2007, Pages 7742-7743

Direct palladium-catalyzed alkynylation of N-fused heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; PALLADIUM;

EID: 34347241643     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja072718l     Document Type: Article
Times cited : (257)

References (41)
  • 1
    • 34250655628 scopus 로고    scopus 로고
    • For recent reviews, see: a, published online
    • For recent reviews, see: (a) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev., published online, 2007, http://dx.doi.org/10.1039/b606984n.
    • (2007) Chem. Soc. Rev
    • Seregin, I.V.1    Gevorgyan, V.2
  • 3
    • 0037094021 scopus 로고    scopus 로고
    • For mechanistic studies on Pd-catalyzed arylation of electron-rich heterocycles, see: a
    • For mechanistic studies on Pd-catalyzed arylation of electron-rich heterocycles, see: (a) Okazawa, T.; Satoh, T.; Miura, M.; Nomura, M. J. Am. Chem. Soc. 2002, 124, 5286.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 5286
    • Okazawa, T.1    Satoh, T.2    Miura, M.3    Nomura, M.4
  • 16
    • 31944442069 scopus 로고    scopus 로고
    • For Pd-catalyzed arylation of electron-defficient heterocycles and simple arenes, see: a
    • For Pd-catalyzed arylation of electron-defficient heterocycles and simple arenes, see: (a) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 1066
    • Garcia-Cuadrado, D.1    Braga, A.A.C.2    Maseras, F.3    Echavarren, A.M.4
  • 20
    • 17044366225 scopus 로고    scopus 로고
    • For involvement of Pd(II/IV) catalytic cycle in direct C-H functionalizations, see for example: (a) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
    • For involvement of Pd(II/IV) catalytic cycle in direct C-H functionalizations, see for example: (a) Giri, R.; Chen, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
  • 36
    • 0005891632 scopus 로고
    • N-fused pyrroloheterocycles are known to be among the most electron-rich heterocyclic cores. See, for example:, Thieme: Stuttgart, Germany, /1, 2a, pp
    • N-fused pyrroloheterocycles are known to be among the most electron-rich heterocyclic cores. See, for example: Behnisch, A.; Behnisch, P.; Eggenweiler, M.; Wallenhorst, T. Indolizine. In Houben-Weyl; Thieme: Stuttgart, Germany, 1994; Vol. E6b/1, 2a, pp 323-450.
    • (1994) Houben-Weyl , vol.E6b , pp. 323-450
    • Behnisch, A.1    Behnisch, P.2    Eggenweiler, M.3
  • 37
    • 34347264191 scopus 로고    scopus 로고
    • Trial attempts with non-fused heterocycles, such as pyrroles, under these reaction conditions, afforded low yields of the corresponding alkynylation products. Further studies on the scope of this transformation are underway in our group
    • Trial attempts with non-fused heterocycles, such as pyrroles, under these reaction conditions, afforded low yields of the corresponding alkynylation products. Further studies on the scope of this transformation are underway in our group.
  • 38
    • 34347239747 scopus 로고    scopus 로고
    • For preparation of bromoalkynes, see Supporting Information
    • For preparation of bromoalkynes, see Supporting Information.
  • 39
    • 34347261790 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 40
    • 0037323519 scopus 로고    scopus 로고
    • Carbon-carbon bond forming reactions proceeding via C-H activation motif usually exhibit much higher KIE. See, for example: Jones, W. D. Acc. Chem. Res. 2003, 36, 140
    • Carbon-carbon bond forming reactions proceeding via C-H activation motif usually exhibit much higher KIE. See, for example: Jones, W. D. Acc. Chem. Res. 2003, 36, 140.
  • 41
    • 34347233520 scopus 로고    scopus 로고
    • The reaction was stopped at 60% conversion to avoid thermal decomposition of the product
    • The reaction was stopped at 60% conversion to avoid thermal decomposition of the product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.