메뉴 건너뛰기




Volumn 49, Issue 22, 2010, Pages 3819-3822

Activation of C-F bonds in preference to C-I bonds: Difluoromethylation of lithium enolates with trifluoromethyl iodide

Author keywords

Cleavage reactions; Enolates; Fluorine; Lithium

Indexed keywords

C-F BONDS; CLEAVAGE REACTION; ENOLATES; LITHIUM ENOLATES; TRANSITION METAL CATALYSTS; TRIFLUOROMETHYL;

EID: 77952655591     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201000435     Document Type: Article
Times cited : (35)

References (42)
  • 10
    • 66249097754 scopus 로고    scopus 로고
    • and references therein.
    • H. Amii, K. Uneyama, Chem. Rev. 2009,109, 2119-2183, and references therein.
    • (2009) Chem. Rev. , vol.109 , pp. 2119-2183
    • Amii, H.1    Uneyama, K.2
  • 12
    • 0003181446 scopus 로고
    • Ed. : X D. Morrison, Academic Press, New York, chap. 2.
    • C. H. Heathcock in Asymmetric Synthesis, Vol.3 (Ed. : X D. Morrison), Academic Press, New York, 1984, chap. 2.
    • (1984) Asymmetric Synthesis , vol.3
    • Heathcock, C.H.1
  • 26
    • 0000449913 scopus 로고
    • Review on the construction of quaternary carbon centers: a) S. F. Martin, Tetrahedron 1980, 36, 419-460;
    • (1980) Tetrahedron , vol.36 , pp. 419-460
    • Martin, S.F.1
  • 27
    • 0001521888 scopus 로고
    • b) K. Fuji, Chem. Rev. 1993, 93, 2037-2066;
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 29
    • 0002064932 scopus 로고
    • Ed.: M. Schlosser, Wiley, Chichester, and references therein.
    • Li-F interaction plays an important role in regioselective deprotonation: M. Schlosser in Organometallics in Synthesis-A Manual (Ed.: M. Schlosser), Wiley, Chichester, 1994, pp. 1-166, and references therein.
    • (1994) Organometallics in Synthesis-A Manual , pp. 1-166
    • Schlosser, M.1
  • 30
    • 77952618307 scopus 로고    scopus 로고
    • The high lattice energy of LiF relative to other alkali metal fluorides is also a possible reason for the high yield when using Li enolate.
    • The high lattice energy of LiF relative to other alkali metal fluorides is also a possible reason for the high yield when using Li enolate.
  • 32
    • 84987564680 scopus 로고
    • The NH-Jt interaction was observed for the Li enolate of pinacolone crystallized in the presence of TriMEDA: T. Laube, J. D. Dunitz, D. Seebach, Helv. Chim. Acta 1985, 68, 1373-1393.
    • (1985) Helv. Chim. Acta , vol.68 , pp. 1373-1393
    • Laube, T.1    Dunitz, J.D.2    Seebach, D.3
  • 33
    • 0001269629 scopus 로고
    • D. Seebach, Angew. Chem. 1988, 100, 1685 -1715 ;
    • (1988) , vol.100 , pp. 1685-1715
    • Seebach, D.1    Chem, A.2
  • 34
    • 84990085779 scopus 로고
    • and references therein.
    • Angew. Chem. Int. Ed. Engl. 1988, 27, 1624-1654, and references therein.
    • (1988) Angew. Chem. Int. Ed. Engl. , vol.27 , pp. 1624-1654
  • 35
    • 0033401656 scopus 로고    scopus 로고
    • and references therein.
    • B. L. Lucht, D. B. Collum, Acc. Chem. Res 1999, 32, 1035-1042, and references therein.
    • (1999) Acc. Chem. Res , vol.32 , pp. 1035-1042
    • Lucht, B.L.1    Collum, D.B.2
  • 37
    • 34250883890 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 3002-3017.
    • (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 3002-3017
  • 38
    • 77952664927 scopus 로고    scopus 로고
    • The a-trifluoromethylation of lactams will be reported separately. The a-trifluoromethylation of lithium enolates is generally difficult, but can be attained by using a radical, initiator (Refs. [1-5]).
    • The a-trifluoromethylation of lactams will be reported separately. The a-trifluoromethylation of lithium enolates is generally difficult, but can be attained by using a radical, initiator (Refs. [1-5]).
  • 41
    • 77952621953 scopus 로고    scopus 로고
    • 2H-ibuprofen (3) will be reported separately.
    • 2H-ibuprofen (3) will be reported separately.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.