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Pryjomska I, Bartosz-Bechowski H, Ciunik Z, et al. Chemistry of palladium phosphinite (PPh(2)(OR)) and phosphonite (P(OPh)(2)(OH)) complexes: catalytic activity in methoxycarbonylation and Heck coupling reactions. Dalton Trans. 2005;(1):213-20doi: 10.1039/b512835h.
Pryjomska, I., Bartosz-Bechowski, H., Ciunik, Z., Trzeciak, A. M., & Ziółkowski, J. J. (2006). Chemistry of palladium phosphinite (PPh(2)(OR)) and phosphonite (P(OPh)(2)(OH)) complexes: catalytic activity in methoxycarbonylation and Heck coupling reactions. Dalton transactions (Cambridge, England : 2003), (1), 213-20. https://doi.org/10.1039/b512835h
Pryjomska, Iweta, et al. "Chemistry of palladium phosphinite (PPh(2)(OR)) and phosphonite (P(OPh)(2)(OH)) complexes: catalytic activity in methoxycarbonylation and Heck coupling reactions." Dalton transactions (Cambridge, England : 2003) vol. ,1 (2006): 213-20. doi: https://doi.org/10.1039/b512835h
Pryjomska I, Bartosz-Bechowski H, Ciunik Z, Trzeciak AM, Ziółkowski JJ. Chemistry of palladium phosphinite (PPh(2)(OR)) and phosphonite (P(OPh)(2)(OH)) complexes: catalytic activity in methoxycarbonylation and Heck coupling reactions. Dalton Trans. 2006 Jan 07;(1):213-20. doi: 10.1039/b512835h. Epub 2005 Nov 16. PMID: 16357979.
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Dalton Trans. 2006 Jan 07;(1):213-20. doi: 10.1039/b512835h. Epub 2005 Nov 16.

Chemistry of palladium phosphinite (PPh(2)(OR)) and phosphonite (P(OPh)(2)(OH)) complexes: catalytic activity in methoxycarbonylation and Heck coupling reactions.

Dalton transactions (Cambridge, England : 2003)

Iweta Pryjomska, Hubert Bartosz-Bechowski, Zbigniew Ciunik, Anna M Trzeciak, Józef J Ziółkowski

Affiliations

  1. Faculty of Chemistry, University of Wroc?aw, 14 F. Joliot-Curie St., 50-383 Wroc?aw, Poland.

PMID: 16357979 DOI: 10.1039/b512835h

Abstract

The new phosphinite and phosphonite complexes (1-8) are very efficient catalysts for the methoxycarbonylation of iodobenzene and Heck cross-coupling of bromobenzene with butyl acrylate. High catalytic activity of these complexes can be explained by their in situ transformations during the reaction, stimulated by the presence of water, acid (HCl) or base (NEt(3)). Hydrolysis of phosphinite palladium complexes of the form trans-PdCl(2)[PPh(2)(OR)](2) (R = C(6)F(5), 2, (t)Bu 3, or O-menthyl 4) results in the formation of the dimeric complex [mu-ClPd(PPh(2)OH)(PPh(2)O)](2) 5, which is deprotonated by NEt(3), producing a polymeric complex of formula [Pd(P(O)PPh(2))(2)](n) 8. The reverse reaction, protonolysis of 8 with HCl, leads back to 5 and the monomeric complex 5a. The phosphinite complex PdCl(2)[PPh(2)(OBu)](2)1 with a more lipophilic ligand, PPh(2)(OBu), does not undergo hydrolysis under the same conditions. In the reaction of PdCl(2)(cod) with P(OPh)(2)(OH), the new dimer [mu-ClPd(P(OPh)(2)OH)(P(OPh)(2)O)](2) 6 was obtained, whereas reaction of Pd(OAc)(2) with P(OPh)(2)(OH) leads to the polymeric complex [Pd[P(O)(OPh)(2)](2)](n) 7. Protonolysis of 7 with HCl results in the formation of 6.

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