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<i>N</i>,<i>N</i>′‐bridged binuclear NHC palladium complexes: A combined experimental catalytic and computational study for the Suzuki reaction

Ming‐Tsz Chen, Bing‐Yan Hsieh, Yi‐Hung Liu, Kuo‐Hui Wu, Natália Lussari, Ataualpa Albert Carmo Braga

2020Applied Organometallic Chemistry15 citationsDOI

Abstract

This work examines how N ‐donor bridged spacer ligands affect N ‐heterocyclic carbene (NHC) palladium complexes catalytic activities for Suzuki coupling reaction. Different degrees of structural flexibility binuclear NHC palladium complexes were synthesized. The more flexible nitrogen‐based alkyl chain ligand shows similar performance with cycloamine counterparts in the Suzuki coupling reaction. Suzuki coupling examples were used in air and ambient temperature to reach moderate to completion yields in short time. Density functional theory calculations showed that the chelate effect, associated with a single Pd complex mechanism, plays a fundamental role in the pre‐catalysis stage, supporting a reasonable of the kinetic activity observed experimentally.

Topics & Concepts

ChemistryPalladiumCarbeneCatalysisSuzuki reactionLigand (biochemistry)AlkylDensity functional theoryCoupling reactionCombinatorial chemistryComputational chemistryPolymer chemistryOrganic chemistryBiochemistryReceptorCatalytic Cross-Coupling ReactionsN-Heterocyclic Carbenes in Organic and Inorganic ChemistrySynthetic Organic Chemistry Methods