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Volumn 19, Issue 5, 2000, Pages 775-780

Effect of Halide Ligands on the Reactivity of Carbon-Palladium Bonds: Implications for Designing Catalytic Reactions

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EID: 0001630321     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990670h     Document Type: Article
Times cited : (119)

References (67)
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    • For reviews, see: Trost, B. M. Acc. Chem. Res. 1996, 29, 355-364. Byers, P. K. Coord. Chem. Rev. 1995, 146, A409-429. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 96, 2457-2483.
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    • Trost, B.M.1
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    • For reviews, see: Trost, B. M. Acc. Chem. Res. 1996, 29, 355- 364. Byers, P. K. Coord. Chem. Rev. 1995, 146, A409-429. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 96, 2457-2483.
    • (1995) Coord. Chem. Rev. , vol.146
    • Byers, P.K.1
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    • For reviews, see: Trost, B. M. Acc. Chem. Res. 1996, 29, 355- 364. Byers, P. K. Coord. Chem. Rev. 1995, 146, A409-429. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 96, 2457-2483.
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    • Miyaura, N.1    Suzuki, A.2
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    • (1980) Organic Synthesis with Palladium Compounds
    • Tsuji, J.1
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    • Although protonolysis of the C-Pd bond is, in principle, also an important reaction of organopalladium compounds, its study and application are far less reported in the literature than the β-H elimination and other elementary reactions, (a) Cacchi, S.; La Torre, F.; Misisti, D. Tetrahedron Lett. 1979, 25, 4591-4594.
    • (1979) Tetrahedron Lett. , vol.25 , pp. 4591-4594
    • Cacchi, S.1    La Torre, F.2    Misisti, D.3
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    • In the few studied systems involving protonolysis, the formation of protonolysis products was influenced by many factors, and there has been no consensus regarding the reaction mechanism, (a) Yamamura, K. J. Org. Chem. 1978, 43, 724-727.
    • (1978) J. Org. Chem. , vol.43 , pp. 724-727
    • Yamamura, K.1
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    • note
    • The "solvent effect" in benzene may actually be the result of low concentration of free dissociated halide ions. Please see the related discussion on ligand effect.
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    • note
    • The reactions of the acetate complex 7 with acrolein in the presence of different Li salts give similar results to chloro complex 6. The data are included in Supplementary Table 1 (S-Table 1).
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    • When we attempted the reaction of acrolein with the vinyl-palladium generated by halopalladation of an alkyne in the presence of excess triphenylphosphine, no acrolein insertion product was detected. Yagupsky, G.; Mowat, W.; Shortland, A.; Wilkinson, G. J. Chem. Soc., Chem. Commun. 1970, 1369. Cross, R. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: Chichester, 1985; Vol. 2, p 559.
    • (1970) J. Chem. Soc., Chem. Commun. , pp. 1369
    • Yagupsky, G.1    Mowat, W.2    Shortland, A.3    Wilkinson, G.4
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    • Hartley, F. R., Patai, S., Eds.; Wiley: Chichester
    • When we attempted the reaction of acrolein with the vinyl- palladium generated by halopalladation of an alkyne in the presence of excess triphenylphosphine, no acrolein insertion product was detected. Yagupsky, G.; Mowat, W.; Shortland, A.; Wilkinson, G. J. Chem. Soc., Chem. Commun. 1970, 1369. Cross, R. J. In The Chemistry of the Metal-Carbon Bond; Hartley, F. R., Patai, S., Eds.; Wiley: Chichester, 1985; Vol. 2, p 559.
    • (1985) The Chemistry of the Metal-Carbon Bond , vol.2 , pp. 559
    • Cross, R.J.1


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