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Volumn 27, Issue 19, 2008, Pages 4825-4828

Fluorination of nonactivated haloarenes via arynes under mild conditions, resulting from further studies toward Ar-F reductive elimination from palladium(II)

Author keywords

[No Author keywords available]

Indexed keywords

HALOARENES; MILD CONDITIONS; REDUCTIVE ELIMINATIONS;

EID: 54249106704     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800520e     Document Type: Article
Times cited : (70)

References (77)
  • 7
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    • A reviewer's comment prompted us to reemphasize (see ref 5a) that Pd-mediated fluorination reactions reported by Sanford (aromatic),4c Sodeoka (aliphatic),4d and most recently Ritter (aromatic) 4e all employ electrophilic, so-called positive fluorine reagents for the C-F bond formation. This electrophilic fluorination methodology4c-e cannot be used for the highly sought displacement of X in nonactivated ArX (X, I, Br, d, OTf, etc, with fluoride and is therefore rather irrelevant to our approach to metal-catalyzed aromatic nucleophilic fluorination with the F, Scheme 1, Ritter's recent report4e describes the synthesis of fluoroarenes ArF by reacting Selectfluor with stoichiometric quantities of (σ-aryl)palladium reagents. The latter are prepared in five steps, with the overall yield of the ArF products for the entire reaction sequence being in the range of ca. 15-40, usually around 30
    • 4h
  • 9
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    • and references cited therein
    • (d) Hamashima, Y.; Sodeoka, M. Synlett 2006, 1467, and references cited therein.
    • (2006) Synlett , pp. 1467
    • Hamashima, Y.1    Sodeoka, M.2
  • 15
    • 54249101099 scopus 로고    scopus 로고
    • In a recent highlight, the fluorination reaction4e is misinterpreted as catalytic in Pd, performed at room temperature, and important for 18F-PET: Nature 2008,454,471
    • 18F-PET: Nature 2008,454,471.
  • 17
    • 48749095255 scopus 로고    scopus 로고
    • While being of some academic interest, the most recently reported5c Ar-F reductive elemination from Pd(IV) cannot provide foundation for the highly sought catalytic reaction (Scheme 1) because unlike Pd(0, Pd(II) does not oxidatively add haloarenes. The most closely related Ar-Cl reductive eleimation from a similar Pd(IV) complex was earlier reported by Whitfield and Sanford.5d(c) Furuya, T, Ritter, T. J. Am. Chem. Soc. 2008, 130, 10060
    • 5d(c) Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 10060.
  • 35
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    • Complex 5 has been previously detected but not isolated: Paladino, G.; Madec, D.; Prestat, G.; Maitro, G.; Poli, G.; Jutand, A. Organometallics 2007, 26, 455.
    • Complex 5 has been previously detected but not isolated: Paladino, G.; Madec, D.; Prestat, G.; Maitro, G.; Poli, G.; Jutand, A. Organometallics 2007, 26, 455.
  • 43
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    • 19c
    • 19c
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    • 4N]F: Sun, H.; DiMagno, S. G. J. Am. Chem. Soc. 2005, 127, 2050.
    • 4N]F: Sun, H.; DiMagno, S. G. J. Am. Chem. Soc. 2005, 127, 2050.
  • 56
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    • 31P NMR spectra.
    • 31P NMR spectra.
  • 62
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    • Moss, R. A, Platz, M. S, Jones, M, Jr, Eds, Wiley: Hoboken, NJ
    • (f) Winkler, M.; Wenk, H. H.; Sander, W. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr., Eds.; Wiley: Hoboken, NJ, 2004; pp 741-794.
    • (2004) Reactive Intermediate Chemistry , pp. 741-794
    • Winkler, M.1    Wenk, H.H.2    Sander, W.3
  • 64
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    • 21b We have not been able to find either thesis and/or its abstract in the STN International Dissertation Database, Scopus, and Scifinder.
    • 21b We have not been able to find either thesis and/or its abstract in the STN International Dissertation Database, Scopus, and Scifinder.
  • 72
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    • A side reaction of fluoride addition to an independently generated aryne has been documented: Kolomeitsev, A. A.; Vorobyev, M.; Gillandt, H. Tetrahedron Lett. 2008, 49, 449.
    • A side reaction of fluoride addition to an independently generated aryne has been documented: Kolomeitsev, A. A.; Vorobyev, M.; Gillandt, H. Tetrahedron Lett. 2008, 49, 449.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.