Cu‐catalyzed Synthesis of Quinolines by Dehydrogenative Reaction of 2‐Aminobenzyl Alcohol and Ketones: A Combined Experimental and Computational Study

Abstract

Quinoline derivatives are important moieties in bioactive molecules and advanced materials. However, an efficient strategy to synthesize quinoline derivatives remains challenging. Herein, we describe an efficient and practical method for the synthesis of quinolines by Cu-catalyzed cyclization of 2-amino benzyl alcohol with ketones (or secondary alcohols) via an acceptorless dehydrogenation pathway. Interestingly, a range of highly functionalized quinolines is prepared in good yields using low catalyst loading under relatively mild conditions. Furthermore, density functional theory (DFT) calculations are carried out to investigate mechanistic insights for the acceptorless dehydrogenation pathway.

Recent Advances in the Use of 2‐Aminobenzyl Alcohols in the Synthesis of Quinolines, Quinazolines and Other N‐Heterocycles

“…In 2022, several reports on the synthesis of quinoline frameworks from 2‐aminobenzyl alcohols and ketones were presented in the presence of Cu, [44] Ir, [45] Sm [46] . For example, Bera and Soo developed a visible‐light strategy for the construction of quinolines (X=CH) 43 and naphthyridines (X=N) 44 (Scheme 26).…”