Metal–Ligand Cooperative Approach To Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3H)-ones under Mild Aerobic Conditions

2019/07/22 by Siuli Das, Suman Sinha, Deepannita Samanta +5 · 126 citations
Chemistry · #Asymmetric Hydrogenation and Catalysis #Catalysis #Catalytic C–H Functionalization Methods #Chemistry #Combinatorial chemistry #Coupling reaction #Ligand (biochemistry) #Metal #Organic chemistry #Quinazolinone synthesis and applications #Receptor #Redox #Surface modification

paper · doi:10.1021/acs.joc.9b01343

published in The Journal of Organic Chemistry 84(16), 10160-10171 (American Chemical Society)

openalex publication_date 2019/07/22 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

A simple metal–ligand cooperative approach for the dehydrogenative functionalization of alcohols to various substituted quinolines and quinazolin-4(3 H )-ones under relatively mild reaction conditions (≤90 °C) is reported. Simple and easy-to-prepare air-stable Cu(II) complexes featuring redox-active azo-aromatic scaffolds, 2-arylazo-(1,10-phenanthroline) ( L 1, 2 ), are used as catalyst. A wide variety of substituted quinolines and quinazolin-4(3 H )-ones were synthesized in moderate to good isolated yields via dehydrogenative coupling reactions of various inexpensive and easily available starting materials under aerobic conditions. A few control experiments and deuterium labeling studies were carried out to understand the mechanism of the dehydrogenative coupling reactions, which indicate that both copper and the coordinated azo-aromatic ligand participate in a cooperative manner during the catalytic cycle.

Citations

• Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields

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