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Iridium(III) Catalysts with an Amide‐Pendant Cyclopentadienyl Ligand: Double Aromatic Homologation Reactions of Benzamides by Fourfold C−H Activation

Eiki Tomita, Kodai Yamada, Yu Shibata, Ken Tanaka, M. Kojima, Tatsuhiko Yoshino, Shigeki Matsunaga

2020Angewandte Chemie International Edition24 citationsDOIOpen Access PDF

Abstract

Abstract The synthesis, characterization, and catalytic performance of iridium(III) catalysts that bear an amide‐pendant cyclopentadienyl ligand ([Cp A IrI 2 ] 2 ) is reported. These [Cp A IrI 2 ] 2 catalysts were obtained from the complexation of a Cp A ligand precursor with [Ir(cod)OAc] 2 followed by oxidation. Double aromatic homologation reactions of benzamides with alkynes by fourfold C−H activation proceeded in good to high yield with these [Cp A IrI 2 ] 2 catalysts, demonstrating their superior catalytic performance in this challenging transformation.

Topics & Concepts

Cyclopentadienyl complexIridiumChemistryAmideCatalysisLigand (biochemistry)Yield (engineering)Medicinal chemistryOrganic chemistryReceptorMaterials scienceMetallurgyBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis