Rh(III)-Catalyzed <i>N</i> -Amino-Directed C–H Coupling with 3-Methyleneoxetan-2-ones for 1,2-Dihydroquinoline-3-carboxylic Acid Synthesis
Renpeng Zhou, Shuaixin Fan, Lili Fang, Benfa Chu, Jin Zhu
Abstract
Dynamic polarity analysis is proposed herein as a general tool for investigating static polarity and transient polarity and revealing expanded reactivity patterns. Through this analysis formalism, polarity matching has been established for Rh(III)-catalyzed N -amino-directed C–H coupling with 3-methyleneoxetan-2-ones, providing efficient access to 1,2-dihydroquinoline-3-carboxylic acids. The identified reaction, by virtue of the internal oxidative mechanism, showcases mild reaction conditions (room temperature), a short reaction time (2 h), and a generally high product yield.
Topics & Concepts
ChemistryPolarity (international relations)CatalysisYield (engineering)Reactivity (psychology)Carboxylic acidCombinatorial chemistryAmino acidOxidative coupling of methaneStereochemistryMedicinal chemistryOrganic chemistryBiochemistryMetallurgyCellAlternative medicineMedicinePathologyMaterials scienceCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesAsymmetric Hydrogenation and Catalysis