6533b7d6fe1ef96bd126663a

RESEARCH PRODUCT

Investigation of the aqueous transmetalation of π-allylpalladium with indium salt: the use of the Pd(OAc)2–TPPTS catalyst

Gianfranco FontanaMarie-christine ScherrmannAndré Lubineau

subject

Allylic rearrangementInorganic chemistrychemistry.chemical_elementBiochemistryUmpolungCatalysisBenzaldehydeTransmetalationchemistry.chemical_compoundBARBIER-TYPE ALLYLATIONSORGANOMETALLIC REACTIONSPolymer chemistryWATERPhysical and Theoretical ChemistryTPPTSSIALIC-ACIDAqueous solutionIN-SITUOrganic ChemistryMEDIATED ALLYLATIONCARBONYL-COMPOUNDSALCOHOLSREGIOSELECTIVITYORGANIC-SYNTHESISSettore CHIM/06 - Chimica OrganicachemistryPalladium

description

pi-Allylpalladium complexes could be generated in water by the palladium(0) water soluble catalyst prepared in situ from palladium acetate and TPPTS. These complexes were transmetalated with indium to react with benzaldehyde. The aqueous solution of Pd(0)(TPPTS)(n) could be reused without deterioration of the catalyst in the first and second recycling. The system proved to be efficient with primary and secondary allylic substrates. The stereochemical outcome of the allylation through umpolung of allylpalladium, was also studied using models with a restraint conformation.

yearjournalcountryeditionlanguage
2005-04-14Org. Biomol. Chem.
https://doi.org/10.1039/b419231c