Metal-Ligand Cooperative Approach To Achieve Dehydrogenative Functionalization of Alcohols to Quinolines and Quinazolin-4(3H)-ones under Mild Aerobic Conditions
authors Das, S; Sinha, S; Samanta, D; Mondal, R; Chakraborty, G; Brandao, P; Paul, ND
nationality International
journal JOURNAL OF ORGANIC CHEMISTRY
keywords GAMMA-AMINO-ALCOHOLS; NON-INNOCENT LIGANDS; ONE-POT SYNTHESIS; OXIDATIVE SYNTHESIS; O-AMINOBENZAMIDES; RUTHENIUM; KETONES; CYCLIZATION; SECONDARY; QUINAZOLINONES
abstract A simple metal-ligand cooperative approach for the dehydrogenative functionalization of alcohols to various substituted quinolines and quinazolin-4(3H)-ones under relatively mild reaction conditions (<= 90 degrees 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,L-2), are used as catalyst. A wide variety of substituted quinolines and quinazolin-4(3H)-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.
publisher AMER CHEMICAL SOC
issn 0022-3263
isbn 1520-6904
year published 2019
volume 84
issue 16
beginning page 10160
ending page 10171
digital object identifier (doi) 10.1021/acs.joc.9b01343
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000481979200029
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journal analysis (jcr 2019):
journal impact factor 4.335
5 year journal impact factor 4.072
category normalized journal impact factor percentile 85.088
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