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Volumn 60, Issue 27, 2004, Pages 5711-5718

Bis(triphenylphosphine)palladium(II)succinimide as a precatalyst for Suzuki cross-coupling - Subtle effects exerted by the succinimide ligand

Author keywords

Biaryls; Palladium; Succinimide; Suzuki cross coupling

Indexed keywords

BORONIC ACID DERIVATIVE; HALIDE; LIGAND; PALLADIUM; SUCCINIMIDE DERIVATIVE;

EID: 2942580986     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.018     Document Type: Article
Times cited : (47)

References (55)
  • 3
    • 0000037108 scopus 로고    scopus 로고
    • and references cited therein
    • Hartwig J.F. Acc. Chem. Res. 31:1998;852. and references cited therein
    • (1998) Acc. Chem. Res. , vol.31 , pp. 852
    • Hartwig, J.F.1
  • 29
    • 2942552215 scopus 로고    scopus 로고
    • The X-ray structure of 2 has been deposited to the Cambridge crystallographic database (UK): CCDC No. 228518
  • 31
    • 2942548923 scopus 로고    scopus 로고
    • Response factors for GC analysis: 4-nitrobromobenzene, 1.00; 4-nitrobiphenyl, 1.40; triphenylphosphine, 2.30: GC-MS analysis of selected quenched samples was performed to ascertain the identity of the components from the reaction mixture. Linear correlations were seen for three separate concentrations of each component. In the absence of the palladium precatalyst 2, no reaction is observed under the conditions used
  • 32
    • 2942519252 scopus 로고    scopus 로고
    • It is not possible to rule out the formation of higher order polynuclear palladium species, whether they be palladium clusters or colloids, which could be responsible for the catalytic reaction. It should be noted that the formation of bis-ligated palladium(0) species is not a prerequsite for the Suzuki reaction - indeed mono-ligated palladium(0) is able to catalyse the Suzuki reaction more effectively (higher turnover frequencies) which is presumably associated with promoting the rate determining transmetallation step, see:
    • It is not possible to rule out the formation of higher order polynuclear palladium species, whether they be palladium clusters or colloids, which could be responsible for the catalytic reaction. It should be noted that the formation of bis-ligated palladium(0) species is not a prerequsite for the Suzuki reaction - indeed mono-ligated palladium(0) is able to catalyse the Suzuki reaction more effectively (higher turnover frequencies) which is presumably associated with promoting the rate determining transmetallation step, see: Beeby B., Bettington S., Fairlamb I.J.S., Goeta A.E., Kapdi A.R., Niemelä E.H., Thompson A.L. New J. Chem. 28:2004;600-605
    • (2004) New J. Chem. , vol.28 , pp. 600-605
    • Beeby, B.1    Bettington, S.2    Fairlamb, I.J.S.3    Goeta, A.E.4    Kapdi, A.R.5    Niemelä, E.H.6    Thompson, A.L.7
  • 33
    • 2942601071 scopus 로고    scopus 로고
    • The higher catalyst loading was used to facilitate detection of the phosphorus containing species
    • The higher catalyst loading was used to facilitate detection of the phosphorus containing species
  • 34
    • 2942552214 scopus 로고    scopus 로고
    • We have been unable to purify adduct 6 by regular silica-gel column chromatography from this mixture
  • 35
    • 2942580696 scopus 로고    scopus 로고
    • To the best of our knowledge this complex has not been synthesised independently. Given the fact that 4-nitro-phenyl bromide is often used as a benchmark substrate in Pd-catalysed cross-coupling reactions, this is surprising. All common databases, including the Cambridge Crystallographic Database, were searched for details of this complex
    • To the best of our knowledge this complex has not been synthesised independently. Given the fact that 4-nitro-phenyl bromide is often used as a benchmark substrate in Pd-catalysed cross-coupling reactions, this is surprising. All common databases, including the Cambridge Crystallographic Database, were searched for details of this complex
  • 36
    • 2942517618 scopus 로고    scopus 로고
    • We have not isolated any palladium complexes (in a zero or +two oxidation state) from silica-gel chromatography. No yellow bands, which could be indicative of a palladium(II) species, were also not seen
    • We have not isolated any palladium complexes (in a zero or +two oxidation state) from silica-gel chromatography. No yellow bands, which could be indicative of a palladium(II) species, were also not seen


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