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Palladium‐Catalyzed Regioselective Oxidative Annulation of Cyclohexanones and 2‐Aminophenyl Ketones Using Molecular Oxygen as the Sole Oxidant
Author(s) -
Mu WanLu,
Wang Meirong,
Li HuiJing,
Huang DengMing,
Zhang YiYun,
Li ChaoYi,
Liu Ying,
Wu YanChao
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700715
Subject(s) - regioselectivity , chemistry , annulation , palladium , catalysis , redox , oxidative phosphorylation , photochemistry , combinatorial chemistry , oxygen , molecular oxygen , oxidative coupling of methane , organic chemistry , biochemistry
A facile oxidative annulation of cyclohexanones and 2‐aminophenyl ketones that uses molecular oxygen as the sole oxidant is described. The reaction provides a direct approach to acridines, a structural motif for a large number of fluorescent sensors, functional materials, ligands, and pharmaceuticals. In the presence of a palladium catalyst, high regioselectivity is observed when using non‐symmetric 3‐substituted cyclohexanones. With the use of oxygen as the terminal redox moderator, the electron gap of the global redox condensation process is filled and the reaction efficiency is significantly promoted. This protocol possesses many advantages such as using non‐hazardous oxidant and readily available starting materials, high regioselectivity, and water as the only by‐product.