1. A H2O2/HBr system – several directions but one choice: oxidation–bromination of secondary alcohols into mono- or dibromo ketones
- Author
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Alexander O. Terent'ev, Liubov L. Sokova, Gennady I. Nikishin, N. I. Kapustina, and Oleg V. Bityukov
- Subjects
Green chemistry ,010405 organic chemistry ,General Chemical Engineering ,Halogenation ,General Chemistry ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Hydrobromic acid ,Moiety ,Organic chemistry ,Reactivity (chemistry) ,Hydrogen peroxide ,Brønsted–Lowry acid–base theory - Abstract
In this work we found that a H2O2–HBr(aq) system allows synthesis of α-monobromo ketones and α,α′-dibromo ketones from aliphatic and secondary benzylic alcohols with yields up to 91%. It is possible to selectively direct the process toward the formation of mono- or dibromo ketones by varying the amount of hydrogen peroxide and hydrobromic acid. The convenience of application, simple equipment, multifaceted reactivity, and compliance with green chemistry principles make the application of the H2O2–HBr(aq) system very attractive in laboratories and industry. The proposed oxidation–bromination process is selective in spite of known properties of ketones to be oxidized by the Baeyer–Villiger reaction or peroxidated with the formation of compounds with the O–O moiety in the presence of hydrogen peroxide and Bronsted acids.
- Published
- 2018
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