Rh(III)-Catalyzed N-Amino-Directed C-H Coupling with 3-Methyleneoxetan-2-Ones for 1,2-Dihydroquinoline-3-Carboxylic Acid Synthesis

Polarity analysis is important for the deduction of organic reactivity but is largely restricted in the static polarity analysis regime. Dynamic polarity analysis is proposed herein as an expansive tool for quest into both static polarity and transient polarity, allowing the revelation of an augmented pool of 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 a mild reaction condition (room temperature), a short reaction time (2 h), and a generally high product yield. Taken together, the integration of static and dynamic polarity analysis creates a unified foundational framework for reactivity deduction and reactivity classification, in both organic and organometallic chemistry.