Alpha-Oxygenation of Ketones Using TEMPO Disproportionation

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2026-10-16 Epub Date: 2026-10-06 DOI:10.1021/acs.joc.6c01554

Madison A. Chupela, Jeremy M. Williamson, Brett N. Hemric

引用次数: 0

Abstract

The alpha-oxygenation of ketones via acid-driven TEMPO disproportionation is reported. This straightforward and robust protocol from simple starting materials exhibits an excellent substrate scope in terms of scaffold substitutions, selectivity, and functional group tolerance, with substrate limitations elucidated and highlighted. Furthermore, the mechanism was probed by way of UV–visible spectroscopy, deuterium scrambling experiments, kinetic isotope effect, and Hammett analysis to illustrate the reaction dynamics.

查看原文本刊更多论文

使用TEMPO歧化的酮的α -氧合

摘要报道了酮类化合物通过酸驱动的TEMPO歧化反应的α -氧合反应。从简单的起始材料开始，这种简单而稳健的方案在支架取代、选择性和官能团耐受性方面表现出良好的底物范围，并强调了底物的局限性。通过紫外可见光谱、氘置乱实验、同位素动力学效应和Hammett分析等方法对反应机理进行了探讨。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.