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Volumn 31, Issue 9, 2012, Pages 3527-3538

Pyridine-assisted chlorinations and oxidations by palladium(IV)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC ALCOHOLS; CATALYTIC CHLORINATION; ENHANCED REACTIVITY; IN-SITU FORMATIONS; ORGANIC SUBSTRATE;

EID: 84861181838     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300007w     Document Type: Article
Times cited : (22)

References (141)
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    • Racowski, J. M.; Sanford, M. S., Carbon-Heteroatom Bond-Forming Reductive Elimination from Palladium(IV) Complexes. In Higher Oxidation State Organopalladium and Platinum Chemistry; Canty, A. J., Ed.; Springer: Berlin, 2011; Vol. 35, pp 61-84.
    • (2011) Higher Oxidation State Organopalladium and Platinum Chemistry , vol.35 , pp. 61-84
    • Racowski, J.M.1    Sanford, M.S.2
  • 2
    • 79952391315 scopus 로고    scopus 로고
    • Palladium(IV) Complexes as Intermediates in Catalytic and Stoichiometric Cascade Sequences Providing Complex Carbocycles and Heterocycles
    • In, Canty, A. J. Springer: Berlin, Vol.
    • Malinakova, H. C., Palladium(IV) Complexes as Intermediates in Catalytic and Stoichiometric Cascade Sequences Providing Complex Carbocycles and Heterocycles. In Higher Oxidation State Organopalladium and Platinum Chemistry, Canty, A. J., Ed.; Springer: Berlin, 2011; Vol. 35, pp 85-109.
    • (2011) Higher Oxidation State Organopalladium and Platinum Chemistry , vol.35 , pp. 85-109
    • Malinakova, H.C.1
  • 53
    • 80755123500 scopus 로고    scopus 로고
    • IV functionalization sequence, Sanford has recently demonstrated the viability of such a succession in a stoichiometric C-H bond activation
    • IV functionalization sequence, Sanford has recently demonstrated the viability of such a succession in a stoichiometric C-H bond activation: Racowski, J. M.; Ball, N. D.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18022-18025
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 18022-18025
    • Racowski, J.M.1    Ball, N.D.2    Sanford, M.S.3
  • 88
    • 0002585009 scopus 로고
    • 2 chlorinations of cyclohexene produce II and III in different ratios, depending on the mechanism. For a purely radical mechanisms the ratio II: III is 1.66; for ionic chlorinations the ratio ranges between 3 and 4 depending on the solvent and cyclohexene concentration. Radical pathways of cyclohexene chlorinations also produce substantial amounts of 4-chlorocyclohexene, while this product is not formed under ionic conditions
    • 2 chlorinations of cyclohexene produce II and III in different ratios, depending on the mechanism. For a purely radical mechanisms the ratio II: III is 1.66; for ionic chlorinations the ratio ranges between 3 and 4 depending on the solvent and cyclohexene concentration. Radical pathways of cyclohexene chlorinations also produce substantial amounts of 4-chlorocyclohexene, while this product is not formed under ionic conditions: Poutsma, M. L. J. Am. Chem. Soc. 1965, 87, 2161-2171
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 2161-2171
    • Poutsma, M.L.1
  • 98
    • 33845340540 scopus 로고
    • The antisymbiosis concept states "two soft ligands in mutual trans-position will have a destabilizing effect on each other when attached to a class b metal". See
    • The antisymbiosis concept states "two soft ligands in mutual trans-position will have a destabilizing effect on each other when attached to a class b metal". See: Pearson, R. G. Inorg. Chem. 1973, 12, 712-713
    • (1973) Inorg. Chem. , vol.12 , pp. 712-713
    • Pearson, R.G.1
  • 108
    • 0003784649 scopus 로고
    • In; Wiley-VCH: Weinheim, Germany, pp. At the end of Chapter 4.2 ("Substitution in Octahedral Complexes") Wilkins states on p 211: "Associative (A) Mechanisms are extremely rare and it is uncertain whether an authentic example exists."
    • Wilkins, R. G. In Kinetics and Mechanism of Reactions of Transition Metal Complexes; Wiley-VCH: Weinheim, Germany, 1991; pp 199-256. At the end of Chapter 4.2 ("Substitution in Octahedral Complexes") Wilkins states on p 211: "Associative (A) Mechanisms are extremely rare and it is uncertain whether an authentic example exists."
    • (1991) Kinetics and Mechanism of Reactions of Transition Metal Complexes , pp. 199-256
    • Wilkins, R.G.1
  • 126
    • 13344275845 scopus 로고
    • II complexes, it was conceivable that cyclohexene would coordinate to 3 and 4b and thereby altering the propensity of the metal to become oxidized
    • II complexes, it was conceivable that cyclohexene would coordinate to 3 and 4b and thereby altering the propensity of the metal to become oxidized: Albano, V. G.; Natile, G.; Panunzi, A. Coord. Chem. Rev. 1994, 133, 67-114
    • (1994) Coord. Chem. Rev. , vol.133 , pp. 67-114
    • Albano, V.G.1    Natile, G.2    Panunzi, A.3
  • 131
    • 0000091057 scopus 로고
    • - is regarded as a weakly coordinating counterion, many coordination complexes with covalent M-OTf bonds are nevertheless known
    • - is regarded as a weakly coordinating counterion, many coordination complexes with covalent M-OTf bonds are nevertheless known: Lawrance, G. A. Chem. Rev. 1986, 86, 17-33
    • (1986) Chem. Rev. , vol.86 , pp. 17-33
    • Lawrance, G.A.1


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