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Volumn 9, Issue 10, 2007, Pages 1947-1950

N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; COPPER; CROSS LINKING REAGENT; IMINE; NITRILE; OXIME;

EID: 34249287920     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070561w     Document Type: Article
Times cited : (113)

References (49)
  • 4
    • 84879871239 scopus 로고    scopus 로고
    • Recent Advances in Copper-promoted C - Heteroatom Bond Cross-coupling Reactions with Boronic Acids and Derivatives
    • Hall, D. G, Ed, Wiley-VCH: Weinheim
    • (d) Chan, D. M. T.; Lam, P. Y. S. Recent Advances in Copper-promoted C - Heteroatom Bond Cross-coupling Reactions with Boronic Acids and Derivatives. In Boronic Acids - Preparation, Applications in Organic Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; pp 205-240.
    • (2005) Boronic Acids - Preparation, Applications in Organic Synthesis and Medicine , pp. 205-240
    • Chan, D.M.T.1    Lam, P.Y.S.2
  • 33
    • 33644647605 scopus 로고    scopus 로고
    • Recent Advances in Copper-promoted C-Heteroatom Bond Cross-coupling Reactions with Boronic Acids and Derivatives
    • For the direct reaction of boronic acids with benzophenone imine, see:, Hall, D. G, Ed, Wiley-VCH: Weinheim
    • For the direct reaction of boronic acids with benzophenone imine, see: Chan, D. M. T.; Lam, P. Y. S. Recent Advances in Copper-promoted C-Heteroatom Bond Cross-coupling Reactions with Boronic Acids and Derivatives. In Boronic Acids - Preparation, Applications in Organic Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; p 236.
    • (2005) Boronic Acids - Preparation, Applications in Organic Synthesis and Medicine , pp. 236
    • Chan, D.M.T.1    Lam, P.Y.S.2
  • 34
    • 0029979566 scopus 로고    scopus 로고
    • Cu(I) thiophene-2-carboxylate, see: Allred, G.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
    • Cu(I) thiophene-2-carboxylate, see: Allred, G.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
  • 37
    • 34249288734 scopus 로고    scopus 로고
    • Typical Experimental Procedure. To benzophenone oxime O-pentafluorobenzoate (0.1 mmol), E-β-styrylboronic acid (0.12 mmol), and CuTC (2 mg, 0.01 mmol) in a Schlenk tube flushed with argon was added dry DMF (2 mL). The reaction mixture was stirred at 50°C for 3 h and diluted with EtOAc (30 mL), The copper catalyst was removed by passing the reaction mixture through a short pad of silica gel that was buffered with triethylamine. After evaporation of the solvent, the residue was subjected to flash chromatography (silica gel, buffered by triethylamine, eluted with 40:1 hexanes/EtOAc) giving the desired product as a yellow oil in 90% yield.
    • Typical Experimental Procedure. To benzophenone oxime O-pentafluorobenzoate (0.1 mmol), E-β-styrylboronic acid (0.12 mmol), and CuTC (2 mg, 0.01 mmol) in a Schlenk tube flushed with argon was added dry DMF (2 mL). The reaction mixture was stirred at 50°C for 3 h and diluted with EtOAc (30 mL), The copper catalyst was removed by passing the reaction mixture through a short pad of silica gel that was buffered with triethylamine. After evaporation of the solvent, the residue was subjected to flash chromatography (silica gel, buffered by triethylamine, eluted with 40:1 hexanes/EtOAc) giving the desired product as a yellow oil in 90% yield.
  • 40
    • 0001643495 scopus 로고    scopus 로고
    • Gilchrist, T. L.; Rocha Gonsalves, A. M. d'A.; Pinho e Melo, T. M. V. D. Pure Appl. Chem. 1996, 68, 859.
    • (c) Gilchrist, T. L.; Rocha Gonsalves, A. M. d'A.; Pinho e Melo, T. M. V. D. Pure Appl. Chem. 1996, 68, 859.
  • 41
    • 34249333907 scopus 로고    scopus 로고
    • The Beckmann rearrangement may be facilitated by the organostannane: reaction of the same substrate under the same reaction conditions with the analogous boronic acid does not cause formation of the Beckmann product
    • The Beckmann rearrangement may be facilitated by the organostannane: reaction of the same substrate under the same reaction conditions with the analogous boronic acid does not cause formation of the Beckmann product.
  • 42
    • 0030940775 scopus 로고    scopus 로고
    • For the oxidative addition of oxime derivatives to metals such as Re, Pd, and Cu, see: a
    • For the oxidative addition of oxime derivatives to metals such as Re, Pd, and Cu, see: (a) Kusama, H.; Yamashita, Y.; Uchiyama, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 965.
    • (1997) Bull. Chem. Soc. Jpn , vol.70 , pp. 965
    • Kusama, H.1    Yamashita, Y.2    Uchiyama, K.3    Narasaka, K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.