Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research and Development of Natural Products, Yunnan Characteristic Plant Extraction Laboratory, School of Pharmacy, Yunnan University, Kunming, Yunnan 650091, P. R. China.
J Org Chem. 2023 Jul 7;88(13):8114-8122. doi: 10.1021/acs.joc.3c00096. Epub 2023 Jun 22.
The oxidation of primary alcohols to the corresponding carboxylic acids is one of the fundamental and useful reactions in organic synthesis. In this paper, we report our comprehensive results toward the oxidation of primary alcohols and aldehydes to acids via hydride transfer reactions mediated by 1-hydroxycyclohexyl phenyl ketone. Under the strong basic conditions of sodium -butoxide, the room temperature oxidations tolerate a range of functional groups, including vulnerable -butanesulfinamides, amines, sulfides, olefins, and heterocycles, and provide good to excellent yields. Most importantly, our oxidation procedure can be applied to chemoselective oxidation of primary alcohols and aldehydes to carboxylic acids in the presence of secondary alcohols.
伯醇氧化为相应的羧酸是有机合成中最基本和最有用的反应之一。在本文中，我们报告了通过 1-羟基环己基苯基酮介导的氢化物转移反应将伯醇和醛氧化为酸的综合结果。在正丁醇钠的强碱性条件下，室温氧化可耐受一系列官能团，包括易受影响的丁烷亚磺酰胺、胺、硫醚、烯烃和杂环，并且产率良好至优秀。最重要的是，我们的氧化程序可用于在仲醇存在下选择性氧化伯醇和醛为羧酸。
