Transmetalation reactions. The role of the stabilizing olefin in determining the overall reaction rate

Journal of Organometallic Chemistry

Volumn 693, Issue 21-22, 2008, Pages 3324-3330

  Canovese, Luciano ^a   Visentin, Fabiano ^a   Levi, Carlo ^a   Santo, Claudio ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

Author keywords

Kinetic study; Palladium(II) butadyenyl complexes; Stille coupling; Transmetalation reaction

Indexed keywords

CHLORINE COMPOUNDS; NANOSTRUCTURED MATERIALS; OLEFINS; PALLADIUM; PALLADIUM COMPOUNDS; REACTION RATES;

BUTADIENYL; DOUBLE BONDS; KINETIC STUDY; PALLADIUM(II) BUTADYENYL COMPLEXES; REACTION-RATE; STILLE COUPLING; SYSTEMATIC STUDY; TRANSMETALATION REACTION; TRANSMETALATION REACTIONS;

RATE CONSTANTS;

EID: 52049088486     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.07.028     Document Type: Article

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53. 3 at 298 K. In the case of complex 1A we have also studied the reaction in the presence of but-2-ynedioic acid dimethyl ester (dma) yielding the palladacyclopentadiene derivative. The reactivity induced by dma lies between those of nq and dmfu.
54. We chose fumaronitrile as the target olefin since the ensuing reactivity rates were within reasonable time intervals and because the reactions carried out in the presence of ma underwent a further slow attack of the stannane to the carbonyl groups of the coordinated maleic anhydride to give 1,8-diphenyl-oct-4-ene-1,7-diyne-3,6-dione, di(n-butyl-stannane)oxide, the free ligand MeN-SPh and palladium metal according to the reaction in the following scheme 4. It is noteworthy that the reaction between free ma and stannane carried out in the presence of complex 1A is remarkably slower than that reported above. Apparently, the side reaction noticed during the kinetic investigation is the attack of the stannane to the coordinated ma in the Pd(0) derivative.{A figure is presented}
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