4-(N,N-Dimethylamino)pyridine Hydrochloride as a Recyclable Catalyst for Acylation of Inert Alcohols: Substrate Scope and Reaction Mechanism

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• 作者：Zhihui Liu ; Qiaoqiao Ma ; Yuxiu Liu ; Qingmin Wang
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：January 3, 2014
• 年：2014
• 卷：16
• 期：1
• 页码：236-239
• 全文大小：296K
• ISSN：1523-7052

文摘

4-(N,N-Dimethylamino)pyridine hydrochloride (DMAP路HCl), a DMAP salt with the simplest structure, was used as a recyclable catalyst for the acylation of inert alcohols and phenols under base-free conditions. The reaction mechanism was investigated in detail for the first time; DMAP路HCl and the acylating reagent directly formed N-acyl-4-(N鈥?/i>,N鈥?/i>-dimethylamino)pyridine chloride, which was attacked by the nucleophilic substrate to form a transient intermediate that released the acylation product and regenerated the DMAP路HCl catalyst.