Proton-exchanged montmorillonite-mediated reactions of聽methoxybenzyl esters and ethers

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• 作者：Dongyin Chen^a ; Chang Xu^a ; Jie Deng^a ; Chunhuan Jiang^a ; Xiaoan Wen^a ; Lingyi Kong^a ; Ji Zhang^b ; ^{jzhangcpu@126.com" class="auth_mail} ; Hongbin Sun^a ; ^b ; ^{hbsun2000@yahoo.com" class="auth_mail}
• 关键词：Proton-exchanged montmorillonite ; Quinone methides ; Benzylation reactions ; p-Methoxybenzyl group ; Deprotection
• 刊名：Tetrahedron
• 出版年：18 March, 2014
• 年：2014
• 卷：70
• 期：11
• 页码：1975-1983
• 全文大小：2075 K

文摘

Proton-exchanged montmorillonite (H-mont) was found to be an eco-friendly and cost-effective catalyst for the generation of O-methylated quinone methides (QM) from the corresponding p or o-methoxybenzyl esters and ethers. Nucleophilic trapping of the O-methylated QM with arenes, alcohols, 1,3-dicarbonyl compounds, silyl enol ethers, and allylsilanes has been carried out, respectively, leading to eco-friendly benzylation reactions. Using this protocol, H-mont-mediated deprotection of PMB-protected esters and ethers have been realized for the first time. This work would pave the way for further exploration in O-alkylated QM that are of chemical and biological significance.