메뉴 건너뛰기




Volumn 73, Issue 16, 2008, Pages 6441-6444

Copper-mediated N-cyclopropylation of azoles, amides, and sulfonamides by cyclopropylboronic acid

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CYCLOPROPYL; DICHLORO ETHANE; EXCELLENT YIELDS; SODIUM CARBONATES;

EID: 50149089044     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801033y     Document Type: Article
Times cited : (62)

References (57)
  • 5
    • 0001781293 scopus 로고    scopus 로고
    • Cyclopropane Derivatives and their Diverse Biological Activities
    • de Meijere, A, Ed, Springer-Verlag: Berlin
    • (b) Salaün, J. Cyclopropane Derivatives and their Diverse Biological Activities. In Topics in Current Chemistry; de Meijere, A., Ed.; Springer-Verlag: Berlin, 2000; Vol. 207, pp 1-67.
    • (2000) Topics in Current Chemistry , vol.207 , pp. 1-67
    • Salaün, J.1
  • 22
    • 0013418182 scopus 로고    scopus 로고
    • Palladium-Catalyzed Amination of Aryl Halides and Related Reactions
    • Negishi, E.-I, de Meijere, A, Eds, Wiley-Interscience: New York
    • (b) Hartwig, J. F. Palladium-Catalyzed Amination of Aryl Halides and Related Reactions. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; Vol. 1, pp 1051-1096.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.1 , pp. 1051-1096
    • Hartwig, J.F.1
  • 23
    • 0000157513 scopus 로고    scopus 로고
    • Practical Palladium Catalysts for C-N and C-O Bond Formation
    • Miyaura, N, Ed, Springer-Verlag: Berlin
    • (c) Muci, A. R.; Buchwald, S. L. Practical Palladium Catalysts for C-N and C-O Bond Formation. In Topics in Current Chemistry; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219, pp 133-205.
    • (2002) Topics in Current Chemistry , vol.219 , pp. 133-205
    • Muci, A.R.1    Buchwald, S.L.2
  • 24
    • 0345708168 scopus 로고    scopus 로고
    • For a review involving copper, see: d
    • For a review involving copper, see: (d) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
    • (2003) Angew. Chem., Int. Ed , vol.42 , pp. 5400-5449
    • Ley, S.V.1    Thomas, A.W.2
  • 30
    • 84879871239 scopus 로고    scopus 로고
    • Recent Advances in Copper-promoted C-Heteroatom Bond Cross-coupling Reaction with Boronic Acids and derivatives
    • Hall, D. G, Ed, Wiley-VCH: Weinheim, Germany
    • Chan, D. M. T.; Lam, P. Y. S. Recent Advances in Copper-promoted C-Heteroatom Bond Cross-coupling Reaction with Boronic Acids and derivatives. In Boronic Acids: Preparation and Application in Organic Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VCH: Weinheim, Germany, 2005; pp 205-240.
    • (2005) Boronic Acids: Preparation and Application in Organic Synthesis and Medicine , pp. 205-240
    • Chan, D.M.T.1    Lam, P.Y.S.2
  • 43
    • 38349095933 scopus 로고    scopus 로고
    • Such reaction conditions have been used recently in copper-catalyzed aerobic oxidative amination: Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833-834.
    • Such reaction conditions have been used recently in copper-catalyzed aerobic oxidative amination: Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833-834.
  • 51
    • 50149105600 scopus 로고    scopus 로고
    • Most of the transformations reported in Table 2 worked in the presence of catalytic amount of copper salt. However, longer reaction time was required with reduced yields of coupling product.
    • Most of the transformations reported in Table 2 worked in the presence of catalytic amount of copper salt. However, longer reaction time was required with reduced yields of coupling product.
  • 52
    • 50149099747 scopus 로고    scopus 로고
    • The structure of 5i was confirmed by NOE experiment.
    • The structure of 5i was confirmed by NOE experiment.
  • 53
    • 50149098937 scopus 로고    scopus 로고
    • Preliminary experiments indicate that anilines could be cyclopropylated under established conditions. However, no cyclopropylated product was isolated when N-methyl benzylamine was submitted to the identical reaction conditions. We are working towards the optimization of these reactions and the results will be reported in due course.
    • Preliminary experiments indicate that anilines could be cyclopropylated under established conditions. However, no cyclopropylated product was isolated when N-methyl benzylamine was submitted to the identical reaction conditions. We are working towards the optimization of these reactions and the results will be reported in due course.
  • 56
    • 0032492980 scopus 로고    scopus 로고
    • For an initial report on copper-mediated C-O bond formation between phenol and arylboronic acid, see
    • (b) For an initial report on copper-mediated C-O bond formation between phenol and arylboronic acid, see: Evans, D. A.; Katz, J. L.; West, T. R Tetrahedron Lett. 1998, 39, 2937-2940.
    • (1998) Tetrahedron Lett , vol.39 , pp. 2937-2940
    • Evans, D.A.1    Katz, J.L.2    West, T.R.3
  • 57
    • 50149107552 scopus 로고    scopus 로고
    • One referee pointed out that the presence of a tiny amount of oxygen in the reaction media might serve to oxidize the copper salt. We are working to understand this coupling process. However, we note that the reactions performed under argon atmosphere provided indeed the reproducible results with several different substrates
    • One referee pointed out that the presence of a tiny amount of oxygen in the reaction media might serve to oxidize the copper salt. We are working to understand this coupling process. However, we note that the reactions performed under argon atmosphere provided indeed the reproducible results with several different substrates.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.