6533b85afe1ef96bd12b95ec

RESEARCH PRODUCT

tBuLi-Mediated One-Pot Direct Highly Selective Cross-Coupling of Two Distinct Aryl Bromides.

Carlos VilaCarlos VilaMartín Fañanás-mastralMartín Fañanás-mastralBernard FeringaSara CembellinMassimo GianneriniValentin Hornillos

subject

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 BIARYLSPalladium

description

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.

10.1002/chem.201502709https://pubmed.ncbi.nlm.nih.gov/26356873