Search results for "ORGANIC-SYNTHESIS"

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

2005

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.

Allylic rearrangementInorganic chemistrychemistry.chemical_elementBiochemistryUmpolungCatalysisBenzaldehydeTransmetalationchemistry.chemical_compoundBARBIER-TYPE ALLYLATIONSORGANOMETALLIC REACTIONSPolymer chemistryWATERPhysical and Theoretical ChemistryTPPTSSIALIC-ACIDAqueous solutionIN-SITUOrganic ChemistryMEDIATED ALLYLATIONCARBONYL-COMPOUNDSALCOHOLSREGIOSELECTIVITYORGANIC-SYNTHESISSettore CHIM/06 - Chimica OrganicachemistryPalladiumOrg. Biomol. Chem.
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tBuLi-Mediated One-Pot Direct Highly Selective Cross-Coupling of Two Distinct Aryl Bromides.

2015

A Pd-catalyzed direct cross-coupling of two distinct aryl bromides mediated by tBuLi is described. The use of [Pd-PEPPSI-IPr] or [Pd-PEPPSI-IPent] as catalyst allows for the efficient one-pot synthesis of unsymmetrical biaryls at room temperature. The key for this selective cross-coupling is the use of an ortho-substituted bromide that undergoes lithium-halogen exchange preferentially.

Stereochemistry22'-BIPYRIDINE COMPLEX2chemistry.chemical_elementORGANOLITHIUM COMPOUNDSCatalysisCatalysischemistry.chemical_compoundLOW-TEMPERATUREBromideOrganolithium compoundscross-couplingN-heterocyclic carbenesGRIGNARD-REAGENTSPD-PEPPSI-IPENT2'-BIPYRIDINE COMPLEXCARBON BOND FORMATIONArylOrganic ChemistryORGANIC-SYNTHESISGeneral ChemistryORTHO-SUBSTITUTED BIARYLSpalladiumHighly selectiveCombinatorial chemistryFUNCTIONALIZED ARYLCoupling (electronics)biarylschemistrylithiumOrganic synthesisUNSYMMETRICAL BIARYLSPalladiumChemistry (Weinheim an der Bergstrasse, Germany)
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