Oxidation of Aromatic Aldehydes to Esters: A Sulfate Radical Redox System

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• 作者：Ya-Fei Guo ; Sajid Mahmood ; Bao-Hua XuXiao-Qian Yao ; Hong-Yan He ; Suo-Jiang Zhang
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：82
• 期：3
• 页码：1591-1599
• 全文大小：569K
• ISSN：1520-6904

文摘

A mild oxidative esterification of various aromatic aldehydes by sulfate radical redox system was presented. In the reaction pathway exploration, the transiency of MeOSO₃^– was disclosed, which was generated from esterification between the in situ generated HSO₄^– and MeOH, a rate-limiting step in the process. More importantly, the selectivity-controlling step was represented by the subsequent nucleophilic displacement between MeOSO₃^– and aldehydes. The ionic oxidant 1a ((NH₄)₂S₂O₈) with more N–H numbers in the cation, as compared with 1c ((n-Bu₄N)₂S₂O₈) and 1d ((PyH)₂S₂O₈), has better performance in the oxidative esterification of aldehydes.