Identification of the effective palladium(0) catalytic species generated in situ from mixtures of pd(dba)2 and bidentate phosphine ligands. Determination of their rates and mechanism in oxidative addition

Journal of the American Chemical Society

Volumn 119, Issue 22, 1997, Pages 5176-5185

  Amatore, Christian ^a   Broeker, Gregory ^a   Jutand, Anny ^a   Khalil, Fouad ^b  

^a ECOLE NORMALE SUPÉRIEURE   (France)

^b SIDI MOHAMED BEN ABDELLAH UNIVERSITY   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; NUCLEAR MAGNETIC RESONANCE; OXIDATION; POTENTIOMETRY;

EID: 0030743672     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9637098     Document Type: Article

References (62)

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35. In other words, the first dba ligand is easily exchanged by two phosphine ligands, while the second one is hard to remove. We ascribe this result, surprising at first glance, to a conflict between electronic and steric requirements. Thus, in our view, one dba and two phosphine ligands appear to be the best compromise between electronic factors (which would lead to exchange of the second dba by the third phosphine) and steric constraints (which oppose this exchange).
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40. 2
41. 31P NMR spectrum that the two signals characteristic of Pd(dba)(DIOP) completely disappeared in the presence of phenyl iodide and that the two signals of PhPdI(DIOP) were detected without any other signals that could characterize a byproduct bearing a phosphine ligand. We are thus inclined to conclude that the yield of the oxidative addition is quantitative.
42. 31P NMR spectroscopy or cyclic voltammetry could be performed.
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53. 3 The reaction probably proceeds by substitution of one bidentate ligand L-L by the double bond of the allylic acetate.
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55. 31P NMR spectros copy. As one can see in Table 3, the half time of the oxidative addition with phenyl iodide is rather small, and no degradation of Pd(dba)(DIOP) can occur during this short time. Thus, a degradation of Pd(dba)(DIOP) could not be invoked to explain the nonproportionality to PhI (rate law in eq 12 and intercept different from 0, Figure 4b).
56. -5).
57. 18
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60. 2 by dppf was faster than that by BINAP. Therefore, we conclude that dppf is more basic than BINAP. Note that we are considering here relative kinetic basicities and not thermodynamic basicities.
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