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Volumn 43, Issue 3, 2004, Pages 343-345

N-Trialkylsilylimines as Coupling Partners for Pd-Catalyzed C-N Bond-Forming Reactions: One-Step Synthesis of Imines and Azadienes from Aryl and Alkenyl Bromides

Author keywords

Amination; Azadienes; Cross coupling; Imines; Palladium

Indexed keywords

BROMINE COMPOUNDS; CATALYSIS; PALLADIUM; SYNTHESIS (CHEMICAL);

EID: 0347761333     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352808     Document Type: Article
Times cited : (77)

References (34)
  • 1
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    • (Ed: A. Ricci), Wiley-VCH, Weinheim
    • For reviews, see: a) J. F. Hartwig in Modern Amination Methods (Ed: A. Ricci), Wiley-VCH, Weinheim, 2000, pp. 195-262;
    • (2000) Modern Amination Methods , pp. 195-262
    • Hartwig, J.F.1
  • 4
    • 0032560932 scopus 로고    scopus 로고
    • For representative examples of very efficient catalysts in palladium-catalyzed C-N bond forming reactions, see: a) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723;
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 9722-9723
    • Old, D.W.1    Wolfe, J.P.2    Buchwald, S.L.3
  • 7
    • 0037020372 scopus 로고    scopus 로고
    • c) A. Schnyder, A. F. Indolese, M. Studer, H.-U. Blaser, Angew. Chem. 2002, 114, 3820-3823; Angew. Chem. Int. Ed. 2002, 41, 3668-3670
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3668-3670
  • 9
    • 0037122141 scopus 로고    scopus 로고
    • d) J. P. Stambuli, R. Kuwano, J. F. Hartwig, Angew. Chem. 2002, 114, 4940-4942; Angew. Chem. Int. Ed. 2002, 41, 4746-4748;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4746-4748
  • 15
    • 0032486790 scopus 로고    scopus 로고
    • For other ammonia surrogates in Pd-catalyzed aminations, see: reference [4a] and also: a) K. Hori, M. Mori, J. Am. Chem. Soc. 1998, 120, 7651-7652;
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7651-7652
    • Hori, K.1    Mori, M.2
  • 23
    • 0003397781 scopus 로고    scopus 로고
    • (Eds: F. Diederich, P. J. Stang), Wiley-VCH, New York, chap. 10
    • The palladium-catalyzed C-C bond formation involving organosilanes (Hiyama coupling) is a well-known reaction: T. Hiyama in Metal-catalyzed Cross-coupling Reactions (Eds: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998, chap. 10; however, to the best of our knowledge, the analogous C-N bond-forming reaction has not been described previously.
    • (1998) Metal-catalyzed Cross-coupling Reactions
    • Hiyama, T.1
  • 25
    • 0348183377 scopus 로고    scopus 로고
    • note
    • Reactions carried out in the presence of CsF in dioxane as solvent gave rise to the cross-coupling product together with considerable amounts of decomposition materials derived from the imine.
  • 26
    • 0348183376 scopus 로고    scopus 로고
    • note
    • These results indicate that strong nucleophiles tend to promote the N-Si bond cleavage at a much faster rate than the catalytic process itself, giving rise to decomposition of the imine instead of coupling-product formation.
  • 28
    • 0029743317 scopus 로고    scopus 로고
    • The inhibition of the β-elimination pathway was a major challenge in the early work of palladium-catalyzed aryl amination. In fact, catalysts based on chelating ligands such as binap and dppf, so-called second-generation catalysts, favor reductive elimination, thus lowering the amount of β-elimination products: a) J. P. Wolfe, S. Wagaw, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 7215-7216;
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7215-7216
    • Wolfe, J.P.1    Wagaw, S.2    Buchwald, S.L.3
  • 31
    • 0141519681 scopus 로고    scopus 로고
    • The β-elimination pathway in the presence of a Pd catalyst based on 4b was recently adapted into a new method for the oxidation of alcohols: A. S. Guram, X. Bei, H. W. Turner, Org. Lett. 2003, 5, 2485-2487.
    • (2003) Org. Lett. , vol.5 , pp. 2485-2487
    • Guram, A.S.1    Bei, X.2    Turner, H.W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.