메뉴 건너뛰기




Volumn 72, Issue 22, 2007, Pages 8604-8607

Trifluoromethylation of salicyl aldimines

Author keywords

[No Author keywords available]

Indexed keywords

INTRAMOLECULAR BORON COMPLEX; SALICYL ALDIMINES; SODIUM ACETATE; TRIFLUOROMETHYLATION;

EID: 35548947177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701734d     Document Type: Article
Times cited : (27)

References (51)
  • 2
    • 0003907264 scopus 로고
    • Welch, C. T, Eswarakrishnan, S, Eds, John Wiley & Sons: New York
    • (b) Fluorine in Bioorganic Chemistry; Welch, C. T., Eswarakrishnan, S., Eds.; John Wiley & Sons: New York 1991.
    • (1991) Fluorine in Bioorganic Chemistry
  • 5
    • 0141631561 scopus 로고    scopus 로고
    • Radical trifluoromethylation: (a) Gagosz, F.; Zard, S. Z. Org. Lett. 2003, 5, 2655.
    • Radical trifluoromethylation: (a) Gagosz, F.; Zard, S. Z. Org. Lett. 2003, 5, 2655.
  • 9
    • 35548976221 scopus 로고    scopus 로고
    • Electrophilic trifluoromethylation (a) Yagupol'skii, L. M.; Kondratenko, N. Y.; Timofeeva, G. N. Zh. Org. Khim. 1984, 20, 115.
    • Electrophilic trifluoromethylation (a) Yagupol'skii, L. M.; Kondratenko, N. Y.; Timofeeva, G. N. Zh. Org. Khim. 1984, 20, 115.
  • 13
    • 0031140114 scopus 로고    scopus 로고
    • Nucleophilic trifluoromethylation: (a) Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757.
    • Nucleophilic trifluoromethylation: (a) Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757.
  • 20
    • 0006598557 scopus 로고    scopus 로고
    • 3, see: Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195.
    • 3, see: Ruppert, I.; Schlich, K.; Volbach, W. Tetrahedron Lett. 1984, 24, 2195.
  • 31
    • 0035917368 scopus 로고    scopus 로고
    • Nitrones represent another class of substrates with activated C,N double bond, which can be trifluoromethylated using t-BuOK; see: Nelson, D. W.; Owens, J.; Hiraldo, D. J. Org. Chem. 2001, 66, 2572.
    • Nitrones represent another class of substrates with activated C,N double bond, which can be trifluoromethylated using t-BuOK; see: Nelson, D. W.; Owens, J.; Hiraldo, D. J. Org. Chem. 2001, 66, 2572.
  • 39
    • 34547106276 scopus 로고    scopus 로고
    • In a recent contribution from Makosza and co-workers, pyridinium salts were shown to be active electrophiles for the interaction with Me 3-SiCF3 activated by KF/Ph3SnF; see: Loska, R, Majcher, M, Makosza, M. J. Org. Chem. 2007, 72, 5574
    • 3SnF; see: Loska, R.; Majcher, M.; Makosza, M. J. Org. Chem. 2007, 72, 5574.
  • 40
    • 15444365137 scopus 로고    scopus 로고
    • 3 efficiently promotes addition of organometallic reagents to imines. Ma, Y.; Lobkovsky, E.; Collum, D. B. J. Org. Chem. 2005, 70, 2335.
    • 3 efficiently promotes addition of organometallic reagents to imines. Ma, Y.; Lobkovsky, E.; Collum, D. B. J. Org. Chem. 2005, 70, 2335.
  • 41
    • 0038106171 scopus 로고    scopus 로고
    • (b) Bloch, R. Chem. Rev. 1998, 98, 1407.
    • (1998) Chem. Rev , vol.98 , pp. 1407
    • Bloch, R.1
  • 42
    • 35548960913 scopus 로고    scopus 로고
    • 3-mediated addition of perfluoroalkyllithiums to imines see: Uno, H.; Okada, S.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 7, 1165. However, trifluoromethyllithium and magnesium reagents are highly unstable and cannot be used.
    • 3-mediated addition of perfluoroalkyllithiums to imines see: Uno, H.; Okada, S.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 7, 1165. However, trifluoromethyllithium and magnesium reagents are highly unstable and cannot be used.
  • 43
    • 35548929791 scopus 로고    scopus 로고
    • The reactions of Me3SiCF3 are believed to proceed through the five-coordinate siliconate species. For mechanistic discussions, see ref 6 and: (a) Maggiarosa, N, Tyrra, W, Naumann, D, Kirij, N. V, Yagupolskii, Y. L. Angew. Chem, Int. Ed. 1999, 38, 1151
    • 3 are believed to proceed through the five-coordinate siliconate species. For mechanistic discussions, see ref 6 and: (a) Maggiarosa, N.; Tyrra, W.; Naumann, D.; Kirij, N. V.; Yagupolskii, Y. L. Angew. Chem., Int. Ed. 1999, 38, 1151.
  • 45
    • 0037454866 scopus 로고    scopus 로고
    • For chelate boron complexes derived from salicyl aldimines, see: a
    • For chelate boron complexes derived from salicyl aldimines, see: (a) Keizer, T. S.; De Pue, L. J.; Parkin, S.; Atwood, D. A. J. Organomet. Chem. 2003, 666, 103.
    • (2003) J. Organomet. Chem , vol.666 , pp. 103
    • Keizer, T.S.1    De Pue, L.J.2    Parkin, S.3    Atwood, D.A.4
  • 48
    • 35548934167 scopus 로고    scopus 로고
    • 3.
    • 3.
  • 49
    • 35548929377 scopus 로고    scopus 로고
    • It was demonstrated by Mukaiyama that for successful activation of Me3SiCF3 by acetate anion it is necessary to employ sodium or potassium acetate in DMF or tetrabutylammonium acetate in any other solvent, thereby suggesting that the role of DMF is merely to solvate the alkali metal cation; see ref 6b
    • 3 by acetate anion it is necessary to employ sodium or potassium acetate in DMF or tetrabutylammonium acetate in any other solvent, thereby suggesting that the role of DMF is merely to solvate the alkali metal cation; see ref 6b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.