Construction of Heterobiaryl Skeletons through Pd-Catalyzed Cross-Coupling of Nitroarenes and Heterocyclic Arylborononate Esters with a Sterically Demanding NHC Ligand
Wei Chen, Wei Chen, Wanzhi Chen, Wanzhi Chen, Miaochang Liu, Huayue Wu
Abstract
The palladium-catalyzed Suzuki–Miyaura cross-couplings of nitroarenes and heteroarylboronate esters has been developed. A number of heterobiaryl compounds containing pyridine, pyrimidine, quinoline, furan, thiophene, and pyrazole were prepared using [Pd(cinnamyl)Cl]2/2-aryl-5-(2,4,6-triisopropylphenyl)-2,3-imidazolylidene[1,5-a]pyridines as the catalysts in good to excellent yields. The synthetic practicality of this approach is demonstrated through the synthesis of druglike molecules.
Topics & Concepts
ChemistryQuinolineSteric effectsPyridineFuranCatalysisArylThiophenePyrazolePalladiumLigand (biochemistry)Combinatorial chemistryPyrimidineMoleculeMedicinal chemistryOrganic chemistryStereochemistryBiochemistryAlkylReceptorCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsN-Heterocyclic Carbenes in Organic and Inorganic Chemistry