Enantioselective CO<sub>2</sub> Fixation Via a Heck‐Coupling/Carboxylation Cascade Catalyzed by Nickel
Alessandro Cerveri, Riccardo Giovanelli, Davide Sella, Riccardo Pedrazzani, Magda Monari, Olalla Nieto Faza, Carlos Silva López, Marco Bandini
Abstract
fixation is achieved as a second step of a truncated Heck coupling. For this, a new chiral ligand has been prepared and shown to achieve enantiomeric excesses up to 99 %. The overall process efficiently furnishes chiral 2,3-dihydrobenzofuran-3-ylacetic acids, an important class of bioactive products, from easy to prepare starting materials. A combined experimental and computational effort revealed the key steps of the catalytic cycle and suggested the unexpected participation of Ni(I) species in the coupling event.
Topics & Concepts
NickelHeck reactionEnantioselective synthesisCatalysisCombinatorial chemistryCarboxylationCascadeEnantiomerLigand (biochemistry)ChemistryTandemCatalytic cycleCoupling (piping)PalladiumOrganic chemistryMaterials scienceChromatographyReceptorComposite materialBiochemistryMetallurgyCarbon dioxide utilization in catalysisCO2 Reduction Techniques and CatalystsAsymmetric Hydrogenation and Catalysis