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Native Amide‐Directed C(sp<sup>3</sup>)−H Amidation Enabled by Electron‐Deficient Rh<sup>III</sup> Catalyst and Electron‐Deficient 2‐Pyridone Ligand

Takumi Wakikawa, Daichi Sekine, Yuta Murata, Youka Bunno, M. Kojima, Yuki Nagashima, Ken Tanaka, Ken Tanaka, Tatsuhiko Yoshino, Tatsuhiko Yoshino, Shigeki Matsunaga

2022Angewandte Chemie International Edition22 citationsDOI

Abstract

Abstract Trivalent group‐9 metal catalysts with a cyclopentadienyl‐type ligand (CpM III ; M=Co, Rh, Ir, Cp=cyclopentadienyl) have been widely used for directed C−H functionalizations, albeit that their application to challenging C(sp 3 )−H functionalizations suffers from the limitations of the available directing groups. In this report, we describe directed C(sp 3 )−H amidation reactions of simple amide substrates with a variety of substituents. The combination of an electron‐deficient Cp E Rh catalyst (Cp E =1,3‐bis(ethoxycarbonyl)‐substituted Cp) and an electron‐deficient 2‐pyridone ligand is essential for high reactivity.

Topics & Concepts

Cyclopentadienyl complexChemistryAmideCatalysisLigand (biochemistry)Reactivity (psychology)Medicinal chemistryMetalRhodiumStereochemistryOrganic chemistryReceptorAlternative medicinePathologyBiochemistryMedicineCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions
Native Amide‐Directed C(sp<sup>3</sup>)−H Amidation Enabled by Electron‐Deficient Rh<sup>III</sup> Catalyst and Electron‐Deficient 2‐Pyridone Ligand | Litcius