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Organoselenium‐Catalyzed Baeyer–Villiger Oxidation of α,β‐Unsaturated Ketones by Hydrogen Peroxide to Access Vinyl Esters
Author(s) -
Zhang Xu,
Ye Jianqing,
Yu Lei,
Shi Xinkang,
Zhang Ming,
Xu Qing,
Lautens Mark
Publication year - 2015
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.201400957
Subject(s) - chemistry , hydrogen peroxide , catalysis , baeyer–villiger oxidation , diselenide , aryl , organic chemistry , alkyl , enone , peroxide , selenium
By carefully screening the organoselenium pre‐catalysts and optimizing the reaction conditions, simple dibenzyl diselenide was found to be the best pre‐catalyst for Baeyer–Villiger oxidation of ( E )‐α,β‐unsaturated ketones with the green oxidant hydrogen peroxide at room temperature. The organoselenium catalyst used in this reaction could be recycled and reused several times. This new method was suitable not only for methyl unsaturated ketones, but also for alkyl and aryl unsaturated ketones. Therefore, it provided a direct, mild, practical, highly functional group‐tolerant process for the chemoselective preparation of the versatile ( E )‐vinyl esters from the readily available ( E )‐α,β‐unsaturated ketones. A possible mechanism was also proposed to rationalize the activity of the organoselenium catalyst in the presence of hydrogen peroxide in this Baeyer–Villiger oxidation reaction.