α,β-Unsaturated ketones via copper(II) bromide mediated oxidation

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• 作者：James S. Sharley^a ; Ana Marí ; a Collado Pé ; rez^b ; Estela Espinos Ferri^b ; Amadeo Fernandez Miranda^b ; Ian R. Baxendale^a ; ^{i.r.baxendale@durham.ac.uk" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Oxidation ; α ; β-Unsaturated ketones ; Copper catalysis ; Hedione® ; Bromination
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：2 June 2016
• 年：2016
• 卷：72
• 期：22
• 页码：2947-2954
• 全文大小：1229 K

文摘

A protocol for effecting a rapid Saegusa-type oxidation of enol acetates is reported. This new method relies on the in situ elimination of an α-bromo intermediate to generate α,β-unsaturated ketones using copper(II) bromide. The methodology developed was applied to a range of substrates including a cyclohexanone, which could be directly converted to the corresponding phenol derivative. A catalytic system in which a non-masked ketone was successfully oxidised using substoichiometric CuBr₂ was also developed as a proof of principle.