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Volumn 133, Issue 15, 2011, Pages 5732-5735

Benzoquinone-promoted reaction of O2 with a Pd II-hydride

Author keywords

[No Author keywords available]

Indexed keywords

AEROBIC CONDITION; BENZOQUINONES; CATALYZED OXIDATION; HYDRIDE COMPLEXES; MECHANISTIC DIFFERENCES; REDUCTIVE ELIMINATION; STOICHIOMETRIC OXIDANT;

EID: 79954516477     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja200957n     Document Type: Article
Times cited : (48)

References (45)
  • 7
    • 79954456293 scopus 로고    scopus 로고
    • II-catalyzed oxidation reactions has highlighted their similarities: Reference 1e.
    • II-catalyzed oxidation reactions has highlighted their similarities: Reference 1e.
  • 15
    • 25444454085 scopus 로고    scopus 로고
    • II-H complexes, but these do not appear to be operative in catalytic reactions (with the possible exception of the [(-)-sparteine]Pd(H)Cl catalyst system)
    • II-H complexes, but these do not appear to be operative in catalytic reactions (with the possible exception of the [(-)-sparteine]Pd(H)Cl catalyst system): Keith, J. M.; Nielsen, R. J.; Oxgaard, J.; Goddard, W. A., III J. Am. Chem. Soc. 2005, 127, 13172-13179
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 13172-13179
    • Keith, J.M.1    Nielsen, R.J.2    Oxgaard, J.3    Goddard III, W.A.4
  • 21
    • 79954455681 scopus 로고    scopus 로고
    • See Supporting Information for details.
    • See Supporting Information for details.
  • 22
    • 79954466922 scopus 로고    scopus 로고
    • 2 concentration of ∼9 mM in benzene ([Pd-H] = 0.5 mM). See Supporting Information for additional discussion.
    • 2 concentration of ∼9 mM in benzene ([Pd-H] = 0.5 mM). See Supporting Information for additional discussion.
  • 23
    • 79954552592 scopus 로고    scopus 로고
    • 2H). See ref 3b for discussion. The reaction with BQ forms the protic product 6, which could similarly affect the reaction rate and lead to a nonexponential time course.
    • 2H). See ref 3b for discussion. The reaction with BQ forms the protic product 6, which could similarly affect the reaction rate and lead to a nonexponential time course.
  • 35
    • 17344362178 scopus 로고
    • This reactivity is related to the broader class of "oxidatively induced" reductive elimination reactions, promoted by electron-deficient alkenes. For leading references, see
    • This reactivity is related to the broader class of "oxidatively induced" reductive elimination reactions, promoted by electron-deficient alkenes. For leading references, see: Baddley, W. H.; Venanzi, L. M. Inorg. Chem. 1966, 5, 33-35
    • (1966) Inorg. Chem. , vol.5 , pp. 33-35
    • Baddley, W.H.1    Venanzi, L.M.2
  • 42
    • 79954548702 scopus 로고    scopus 로고
    • II species (e.g., see ref 10b). We examined the oxygenation of 1 in the presence of cyclohexenone, methyl acrylate, and maleic anhydride. The reaction was unaffected by the presence of cyclohexenone or methyl acrylate. In the presence of maleic anhydride, 1 undergoes rapid conversion into a complex mixture of products, none of which is Pd-OOH product 4. See Supporting Information for details.
    • II species (e.g., see ref 10b). We examined the oxygenation of 1 in the presence of cyclohexenone, methyl acrylate, and maleic anhydride. The reaction was unaffected by the presence of cyclohexenone or methyl acrylate. In the presence of maleic anhydride, 1 undergoes rapid conversion into a complex mixture of products, none of which is Pd-OOH product 4. See Supporting Information for details.
  • 45
    • 77957719307 scopus 로고    scopus 로고
    • See ref 10h and the following for recent demonstrations of this principle
    • See ref 10h and the following for recent demonstrations of this principle: Engle, K. M.; Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 14137-14151
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 14137-14151
    • Engle, K.M.1    Wang, D.-H.2    Yu, J.-Q.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.