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Volumn 72, Issue 5, 2007, Pages 1856-1858

A practical synthesis of α-aryl methyl ketones via a transition-metal-free Meerwein arylation

Author keywords

[No Author keywords available]

Indexed keywords

MEERWEIN ARYLATION; TETRAFLUOROBORATE SALTS;

EID: 33847677168     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062483g     Document Type: Article
Times cited : (76)

References (76)
  • 1
    • 0021127516 scopus 로고    scopus 로고
    • Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein.
    • Diaryliodonium salts: (a) Varvoglis, A. Synthesis 1984, 709 and references therein.
  • 6
    • 3542997547 scopus 로고
    • and references therein
    • (f) Finet, J.-P. Chem. Rev. 1989, 89, 1487 and references therein.
    • (1989) Chem. Rev , vol.89 , pp. 1487
    • Finet, J.-P.1
  • 8
    • 0013192210 scopus 로고    scopus 로고
    • Organoboron reagents: (h) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein.
    • Organoboron reagents: (h) Brown, H. C.; Nambu, H.; Rogic, M. M. J. Am. Chem. Soc. 1969, 91, 6852 and references therein.
  • 9
    • 0342391377 scopus 로고    scopus 로고
    • Tricarbonylcyclohexadienylium iron salts: (i) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)chromium tricarbonyl:
    • Tricarbonylcyclohexadienylium iron salts: (i) Kelly, L. F.; Narula, A. S.; Birch, A. J. Tetrahedron Lett. 1980, 21, 2455. (π-Chlorobenzene)chromium tricarbonyl:
  • 11
    • 0000166436 scopus 로고    scopus 로고
    • Copper reagents: (k) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697.
    • Copper reagents: (k) Rathke, M. W.; Vogiazoglou, D. J. Org. Chem. 1987, 52, 3697.
  • 15
    • 33847660194 scopus 로고    scopus 로고
    • Aryllead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II; McKillop, A., Ed.; Pergamon: Oxford, 1995; 11, Chapter 11 and references therein.
    • Aryllead reagents: (o) Pinhey, J. T. In Comprehensive Organometallic Chemistry II; McKillop, A., Ed.; Pergamon: Oxford, 1995; Vol. 11, Chapter 11 and references therein.
  • 16
    • 0000626981 scopus 로고    scopus 로고
    • and references therein
    • (p) Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819 and references therein.
    • (1996) Pure Appl. Chem , vol.68 , pp. 819
    • Pinhey, J.T.1
  • 17
    • 33748594965 scopus 로고    scopus 로고
    • Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)-nickel bromide:
    • (q) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans. 1 1997, 1005. π-(2-Methoxyallyl)-nickel bromide:
  • 19
    • 0007604271 scopus 로고    scopus 로고
    • Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550.
    • Grignard reagents with α-bromoketones: (s) Newman, M. S.; Farbman, M. J. Am. Chem. Soc. 1944, 66, 1550.
  • 20
    • 0342826097 scopus 로고    scopus 로고
    • Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
    • Organocadmium reagents: (t) Jones, P. R.; Young, J. R. J. Org. Chem. 1968, 33, 1675.
  • 48
    • 0010862053 scopus 로고    scopus 로고
    • NAr reactions: (e) Scamehorn, R. G.; Bunnett, J. F. J. Org. Chem. 1977, 42, 1457.
    • NAr reactions: (e) Scamehorn, R. G.; Bunnett, J. F. J. Org. Chem. 1977, 42, 1457.
  • 68
    • 33847089135 scopus 로고
    • For the Meerwein arylation of fluorinated olefins, see: m
    • For the Meerwein arylation of fluorinated olefins, see: (m) Rondestvedt, C. S., Jr. J. Org. Chem. 1977, 42, 2618.
    • (1977) J. Org. Chem , vol.42 , pp. 2618
    • Rondestvedt Jr., C.S.1
  • 71
    • 33847638608 scopus 로고    scopus 로고
    • No residual metals were detected in KOAc when tested by ICPMS
    • No residual metals were detected in KOAc when tested by ICPMS.
  • 72
    • 33847646420 scopus 로고    scopus 로고
    • 2OH. Yields varied between 0-35.%.
    • 2OH. Yields varied between 0-35.%.
  • 73
    • 33847642693 scopus 로고    scopus 로고
    • Isopropenyl acetate is available at S40/kg from several suppliers.
    • Isopropenyl acetate is available at S40/kg from several suppliers.
  • 74
    • 33847636195 scopus 로고    scopus 로고
    • Diazonium ions are known to exhibit unstable characteristics that can cause some salts to be explosive. The reactivity of each individual diazonium compound should be investigated to determine their explosive potential before running large scale experiments
    • Diazonium ions are known to exhibit unstable characteristics that can cause some salts to be explosive. The reactivity of each individual diazonium compound should be investigated to determine their explosive potential before running large scale experiments.
  • 75
    • 33847679784 scopus 로고    scopus 로고
    • The dried diazonium salt intermediate has an exotherm of 35.8 cal/g initiating at 100 °C and a smaller exotherm of 3.5cal/g initiating at 175 °C as measured by DSC. Therefore, it is considered a stable intermediate at rt.
    • The dried diazonium salt intermediate has an exotherm of 35.8 cal/g initiating at 100 °C and a smaller exotherm of 3.5cal/g initiating at 175 °C as measured by DSC. Therefore, it is considered a stable intermediate at rt.


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