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Volumn 129, Issue 16, 2007, Pages 5096-5101

Rationale behind the resistance of dialkylbiaryl phosphines toward oxidation by molecular oxygen

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; LIGANDS; OXIDATION; REACTION KINETICS; SUBSTITUTION REACTIONS;

EID: 34247486915     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0683180     Document Type: Article
Times cited : (154)

References (25)
  • 1
    • 0038579438 scopus 로고    scopus 로고
    • Selected recent papers using biaryl phosphines in cross-coupling reactions: (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655.
    • Selected recent papers using biaryl phosphines in cross-coupling reactions: (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653-6655.
  • 9
    • 34247495741 scopus 로고    scopus 로고
    • A number of biaryl phosphines are available from Strem Chemicals, Inc. and Sigma-Aldrich Co
    • A number of biaryl phosphines are available from Strem Chemicals, Inc. and Sigma-Aldrich Co.
  • 10
    • 34247470914 scopus 로고    scopus 로고
    • Biaryl phosphines analyzed via X-crystallography include the following: 2-(2′,4′,6′-triisopropylbiphenyl)diphenylphosphine, 2-(2′,4′,6′-triisopropylbiphenyl)-3,4,5,6-tetramethyl-di- tert-butylphosphine, and 2-(2′,4′,6′- triisopropylbiphenyl)-tert-butyl-N-(1-phenethyl)phosphine. ORTEP diagrams of these structures are included in the Supporting Information.
    • Biaryl phosphines analyzed via X-crystallography include the following: 2-(2′,4′,6′-triisopropylbiphenyl)diphenylphosphine, 2-(2′,4′,6′-triisopropylbiphenyl)-3,4,5,6-tetramethyl-di- tert-butylphosphine, and 2-(2′,4′,6′- triisopropylbiphenyl)-tert-butyl-N-(1-phenethyl)phosphine. ORTEP diagrams of these structures are included in the Supporting Information.
  • 13
    • 34247503433 scopus 로고    scopus 로고
    • Frisch, M. J., et. al. Gaussian 03, revision B.05; Gaussian, Inc.: Wallingford, CT, 2004.
    • Frisch, M. J., et. al. Gaussian 03, revision B.05; Gaussian, Inc.: Wallingford, CT, 2004.
  • 14
    • 34247505272 scopus 로고    scopus 로고
    • For compounds 1-10, a small amount of phosphinate ester was observed via 31P NMR. Phosphinate esters are expected side products from phosphine oxidation: see ref 11, Chemical Equation Presented
    • 31P NMR. Phosphinate esters are expected side products from phosphine oxidation: see ref 11. (Chemical Equation Presented)
  • 17
    • 0037170862 scopus 로고    scopus 로고
    • min from an MESP plot was recently proposed as a quantitative measure of the electron effect of phosphine ligands: Suresh, C. H.; Koga, N. Inorg. Chem. 2002, 41, 1573-1578.
    • min from an MESP plot was recently proposed as a quantitative measure of the electron effect of phosphine ligands: Suresh, C. H.; Koga, N. Inorg. Chem. 2002, 41, 1573-1578.
  • 19
    • 34247508960 scopus 로고    scopus 로고
    • General mechanism: Kosolapoff, G. M.; Maier, L. Organic Phosphorus Compounds; Wiley-Interscience: New York, 1972; 3. p 346.
    • General mechanism: Kosolapoff, G. M.; Maier, L. Organic Phosphorus Compounds; Wiley-Interscience: New York, 1972; Vol. 3. p 346.
  • 20
    • 27844515513 scopus 로고    scopus 로고
    • 2: (a) Rauhut, M. M.; Currier, H. A. J. Org. Chem. 1961, 26, 4626-4628.
    • 2: (a) Rauhut, M. M.; Currier, H. A. J. Org. Chem. 1961, 26, 4626-4628.
  • 22
    • 0000546633 scopus 로고    scopus 로고
    • 2: (a) Nahm, K.; Li, Y.; Evanseck, J. D.; Houk, K. N.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 4879-4884.
    • 2: (a) Nahm, K.; Li, Y.; Evanseck, J. D.; Houk, K. N.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 4879-4884.
  • 25
    • 34247495299 scopus 로고    scopus 로고
    • See the Supporting Information for X-ray crystal structures of L 2PdCl2 complexes
    • 2 complexes.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.