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Volumn 130, Issue 10, 2009, Pages 913-921

Unexpected high regiocontrol in Heck reaction of fluorine-containing electron-deficient olefins-Highly regio- and stereoselective synthesis of β-fluoroalkyl-α-aryl-α,β-unsaturated ketones

Author keywords

Fluoroalkyl , unsaturated ketones; Aryldiazonium salts; Fluorine containing alkenes; Heck reaction; Regioselective; Stereoselective

Indexed keywords


EID: 70249109677     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2009.07.002     Document Type: Article
Times cited : (15)

References (67)
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    • In: Chambers R.D. (Ed). Organofluorine Chemistry (1997), Springer, Berlin
    • (1997) Organofluorine Chemistry
  • 4
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    • Ojima I., McCarthy J.R., and Welch J.T. (Eds), American Chemical Society, Washington, DC
    • In: Ojima I., McCarthy J.R., and Welch J.T. (Eds). Biomedical Frontiers of Fluorine Chemistry (1996), American Chemical Society, Washington, DC
    • (1996) Biomedical Frontiers of Fluorine Chemistry
  • 9
    • 70249150133 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see:
  • 16
    • 33845278864 scopus 로고
    • Ojima I. Chem. Rev. 88 (1988) 1011-1030
    • (1988) Chem. Rev. , vol.88 , pp. 1011-1030
    • Ojima, I.1
  • 32
    • 70249091550 scopus 로고    scopus 로고
    • Recently, several groups and we have reported the stereoselective syntheses of fluoroalkylated alkenes. See
    • Recently, several groups and we have reported the stereoselective syntheses of fluoroalkylated alkenes. See:
  • 46
    • 70249128425 scopus 로고    scopus 로고
    • Several Heck reactions of fluorine-containing alkenes were reported, see
    • Several Heck reactions of fluorine-containing alkenes were reported, see:
  • 49
    • 70249124702 scopus 로고    scopus 로고
    • The Heck reaction of β-fluoroalkylated α,β-unsaturated carbonyl compounds with aryl halide in the presence of palladium catalyst has been reported, however neither the high regioselectivity nor the high yields have been achieved (<48% yield, the regioselectivity = <29:71), see:
    • The Heck reaction of β-fluoroalkylated α,β-unsaturated carbonyl compounds with aryl halide in the presence of palladium catalyst has been reported, however neither the high regioselectivity nor the high yields have been achieved (<48% yield, the regioselectivity = <29:71), see:
  • 51
    • 70249117227 scopus 로고    scopus 로고
    • Recently, we have disclosed a preliminary finding on the Heck reaction of fluorine-containing α,β-unsaturated ketones. See
    • Recently, we have disclosed a preliminary finding on the Heck reaction of fluorine-containing α,β-unsaturated ketones. See:
  • 53
    • 70249088810 scopus 로고    scopus 로고
    • note
    • 1H NMR according to the literature. See Ref. [6c].
  • 54
    • 70249085309 scopus 로고    scopus 로고
    • note
    • Investigation of the reaction conditions for the Heck reaction of 2s with phenyldiazonium salt was investigated in detail, like the case of 2a. However, the satisfactory results were not obtained at all.
  • 60
    • 70249116525 scopus 로고    scopus 로고
    • Arenediazonium salts were prepared according to described procedure. See
    • Arenediazonium salts were prepared according to described procedure. See:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.