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Volumn 29, Issue 15, 2010, Pages 3368-3373

Synthesis and catalytic applications of stable palladium dioxygen complexes

Author keywords

[No Author keywords available]

Indexed keywords

AIR-STABLE; ARYL BROMIDES; CARBONYLATION REACTIONS; CARBONYLATIONS; CATALYTIC APPLICATIONS; CATALYZED COUPLING; DIOXYGENS; HIGH YIELD; REDUCTIVE ATMOSPHERES; STABLE CATALYSTS; SYNTHESIS AND CHARACTERIZATION;

EID: 77955161603     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1003418     Document Type: Article
Times cited : (18)

References (46)
  • 2
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    • Miyaura, N., Ed. Springer-Verlag: Heidelberg, Germany,; Topics in Current Chemistry Series
    • Miyaura, N., Ed. Cross Coupling Reactions: A Practical Guide; Springer-Verlag: Heidelberg, Germany, 2002; Topics in Current Chemistry Series, Vol. 219.
    • (2002) Cross Coupling Reactions: A Practical Guide , vol.219
  • 5
    • 75749151355 scopus 로고    scopus 로고
    • For general reviews see, for example, ref 2 and
    • For general reviews see, for example, ref 2 and: Fleckenstein, C. A.; Plenio, H. Chem. Soc. Rev. 2010, 39, 694
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 694
    • Fleckenstein, C.A.1    Plenio, H.2
  • 21
    • 77955147121 scopus 로고    scopus 로고
    • When the reaction was carried out in toluene, the solution turned brown and no peroxo complex precipitated
    • When the reaction was carried out in toluene, the solution turned brown and no peroxo complex precipitated.
  • 29
    • 77955160853 scopus 로고    scopus 로고
    • 2 is claimed to form the peroxo complex, whereas in ref 11, the same complex was found to be inert to air
    • 2 is claimed to form the peroxo complex, whereas in ref 11, the same complex was found to be inert to air.
  • 30
    • 4143086010 scopus 로고    scopus 로고
    • For solid-state reactions of palladium(0) carbene complexes with air, see ref 11 and
    • For solid-state reactions of palladium(0) carbene complexes with air, see ref 11 and: Konnick, M. M.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 10212
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 10212
    • Konnick, M.M.1    Guzei, I.A.2    Stahl, S.S.3
  • 31
    • 0003998388 scopus 로고    scopus 로고
    • Lide, D. R., Ed. 90 th ed. (Internet Version 2010); CRC Press/Taylor and Francis: Boca Raton, FL
    • Lide, D. R., Ed. CRC Handbook of Chemistry and Physics, 90 th ed. (Internet Version 2010); CRC Press/Taylor and Francis: Boca Raton, FL, 2010.
    • (2010) CRC Handbook of Chemistry and Physics
  • 32
    • 77955167702 scopus 로고    scopus 로고
    • 1H } NMR spectra were observed. Passing of argon via a benzene solution of 3 at 40 °C for 1 h caused formation of only traces of 1 and accumulation of a dark-colored product of decomposition. Heating of the less soluble complex 4 under vacuum at 60 °C for 1 h also did not lead to appreciable deoxygenation
    • 1H } NMR spectra were observed. Passing of argon via a benzene solution of 3 at 40 °C for 1 h caused formation of only traces of 1 and accumulation of a dark-colored product of decomposition. Heating of the less soluble complex 4 under vacuum at 60 °C for 1 h also did not lead to appreciable deoxygenation.
  • 33
    • 77955148518 scopus 로고    scopus 로고
    • nBu, and an unidentified complex exhibiting three signals at 56.7 (s), 28.9 (br s), and 51.3 (br s) ppm in a ca. 2.8:1:0.6 ratio. Reaction conditions were not optimized
    • nBu, and an unidentified complex exhibiting three signals at 56.7 (s), 28.9 (br s), and 51.3 (br s) ppm in a ca. 2.8:1:0.6 ratio. Reaction conditions were not optimized.
  • 34
    • 77955139225 scopus 로고    scopus 로고
    • 6
    • 6.
  • 40
    • 0034127063 scopus 로고    scopus 로고
    • - intermediates in cross-coupling reactions, see for example
    • - intermediates in cross-coupling reactions, see for example: Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314
    • (2000) Acc. Chem. Res. , vol.33 , pp. 314
    • Amatore, C.1    Jutand, A.2
  • 41
    • 77955161335 scopus 로고    scopus 로고
    • note
    • nBu (84%).
  • 42
    • 77955155095 scopus 로고    scopus 로고
    • With regard to the limitation of this protocol, di-ortho-substituted 2-bromomesitylene gave only low yields of 15 and 30% in the reactions with 3 and 4, respectively
    • With regard to the limitation of this protocol, di-ortho-substituted 2-bromomesitylene gave only low yields of 15 and 30% in the reactions with 3 and 4, respectively.
  • 43
    • 70349967850 scopus 로고    scopus 로고
    • For a recent review on palladium-catalyzed carbonylations of aryl halides, see for example: and references therein
    • For a recent review on palladium-catalyzed carbonylations of aryl halides, see for example: Brennführer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114 and references therein
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 4114
    • Brennführer, A.1    Neumann, H.2    Beller, M.3


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