26114-89-6Relevant academic research and scientific papers
Investigation of the aqueous transmetalation of π-allylpalladium with indium salt: The use of the Pd(OAc)2-TPPTS catalyst
Fontana, Gianfranco,Lubineau, Andre,Scherrmann, Marie-Christine
, p. 1375 - 1380 (2005)
π-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. The Royal Society of Chemistry 2005.
Asymmetric palladium-catalyzed allylic alkylation using dialkylzinc reagents: A remarkable ligand effect
Misale, Antonio,Niyomchon, Supaporn,Luparia, Marco,Maulide, Nuno
, p. 7068 - 7073 (2014/07/08)
A serendipitously discovered palladium-catalyzed asymmetric allylic alkylation reaction with diorganozinc reagents, which displays broad functional group compatibility, is reported. This novel transformation hinges on a remarkable ligand effect which overrides the standard "umpolung" reactivity of allyl-palladium intermediates in the presence of dialkylzincs. Owing to its mild conditions, enantioselective allylic alkylations of racemic allylic electrophiles are possible in the presence of sensitive functional groups. Umpole-me-not: A serendipitously discovered palladium-catalyzed asymmetric allylic alkylation reaction with diorganozinc reagents displays broad functional group compatibility. This novel transformation hinges on a remarkable ligand effect which overrides the standard "umpolung" reactivity of allyl-palladium intermediates in the presence of dialkylzinc compounds.
