Open AccessSelenium Dioxide-Mediated Bromination of α,β-Unsaturated Ketones Using N-Bromosuccinimide in the Presence of p-Toluenesulfonic Acid: A Versatile Route for the Synthesis of α′-Bromo-4-arylbut-3-en-2-one and α′,α′-Dibromo-4-arylbut-3-en-2-one
Author(s) -
Tyrchain Mitre Lipon,
Ibakyntiew D. Marpna,
Kmendashisha Wanniang,
O. Risuklang Shangpliang,
Badaker M. Laloo,
Rishanlang gkhlaw,
Bekington Myrboh
Publication year - 2021
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.1c04352
Subject(s) - n bromosuccinimide , p toluenesulfonic acid , halogenation , chemistry , reagent , selenium , toluene , organic chemistry , combinatorial chemistry , catalysis
An efficient method for the synthesis of α,β-unsaturated α'-bromoketones and α,β-unsaturated α',α'-dibromoketones is described using N -bromosuccinimide (NBS) as the brominating agent mediated by selenium dioxide (SeO 2 ) in the presence of p -toluenesulfonic acid (PTSA) monohydrate in toluene. The method is simple, employing easily available shelf reagents to afford a wide range of products in good yields. The method highlighted that simple fine-tuning of the reaction conditions and molar equivalents of the reactants easily affords either mono- or dibrominated products in excellent yields. A number of these products have not been reported in the literature. All of the reactions were carried out in gram-scale quantities.