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One‐Pot Synthesis of Unsymmetrical Benzils by Oxidative Coupling Using Selenium Dioxide and p ‐Toluenesulfonic Acid Monohydrate
Author(s) -
Rohman Md. Rumum,
Kharkongor Icydora,
Rajbangshi Mantu,
Mecadon Hormi,
Laloo Badaker M.,
Sahu Priti R.,
Kharbangar Iadeishisha,
Myrboh Bekington
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101012
Subject(s) - chemistry , selenium , p toluenesulfonic acid , regioselectivity , oxidative coupling of methane , oxidative phosphorylation , solvent , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , biochemistry
The oxidative coupling of the α‐carbon atom of aromatic ketones with unactivated arenes in the presence of selenium dioxide and p ‐toluenesulfonic acid monohydrate is described. A number of unsymmetrical benzils have been prepared in good yields (38–75 %) with high regioselectivity. The generality and functional tolerance of this new protocol is demonstrated. The mechanistic pathway for the oxidative coupling reaction is also described. The reaction displays superiority in terms of minimization of steps with the C–C bond formation promoted by SeO 2 and p TsOH · H 2 O. This method is advantageous as the reactants used as the solvent can be recovered.