Utilization of the inherent nucleophile for regioselective O-acylation of polyphenols via an intermolecular cooperative transesterification

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• 作者：Jingchao Liu^a ; ^b ; ^&dagger ; ; Junjie Fu^c ; ^&dagger ; ; Wenlong Li^a ; Yu Zou^a ; ^b ; Zhangjian Huang^a ; ^b ; ^{cpudahuang@163.com" class="auth_mail" title="E-mail the corresponding author} ; Jinyi Xu^a ; ^{jinyixu@china.com" class="auth_mail" title="E-mail the corresponding author} ; Sixun Peng^a ; ^b ; Yihua Zhang^a ; ^b ; ^{zyhtgd@163.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Regioselective ; Acylation ; Polyphenol ; Green chemistry ; Atom economy ; Inherent nucleophile
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：7 July 2016
• 年：2016
• 卷：72
• 期：27-28
• 页码：4103-4110
• 全文大小：1084 K

文摘

A green and efficient method for regioselective O-acylation of polyphenols has been developed. The acylation can be carried out in potassium carbonate/dimethyl sulphoxide system by utilizing the ‘inherent nucleophile’ via an intermolecular cooperative transesterification under mild condition. This method shows particular advantage in regioselective acylation of polyphenols bearing 2′,4′-dihydroxyacetophenone moiety and can be extended to the synthesis of mono or multiple acetates of polyphenols without this moiety in good yields. Compared with other reported approaches, this method is endowed with atom economy and is more environment-friendly for avoiding the use of any metal-based catalysts.