Proton-exchanged montmorillonite-mediated reactions of methoxybenzyl esters and ethers |
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| Authors: | Dongyin Chen Chang Xu Jie Deng Chunhuan Jiang Xiaoan Wen Lingyi Kong Ji Zhang Hongbin Sun |
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| Institution: | 1. State Key Laboratory of Natural Medicines and Center of Drug Discovery, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing 210009, China;2. Department of Physical Chemistry, China Pharmaceutical University, Nanjing 210009, China |
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| Abstract: | 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. |
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| Keywords: | Proton-exchanged montmorillonite Quinone methides Benzylation reactions p-Methoxybenzyl group Deprotection |
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