Chemoselective epoxidation of electron-deficient olefins with molecular oxygen via conjugated olefins epoxidation and BHT hydroxylation

IF 10.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Science China Chemistry Pub Date : 2024-08-02 DOI:10.1007/s11426-024-2128-7

Jia Nie, Huanfeng Jiang, Chuanle Zhu

引用次数: 0

Abstract

The chemoselective epoxidation of electron-deficient olefins in the presence of electron-rich alkene moieties is reported. This chemoselective epoxidation strategy undergoes a conjugated olefin epoxidation and BHT hydroxylation process to give various useful oxiranes in high yields, especially for the 2-substituted 2-trifluoromethyloxiranes. Importantly, this protocol features mild conditions, is transition-metal free, operationally simple, and gram-scalable, and tolerates diverse functional groups. Drug candidate HSD-16 is synthesized smoothly by this protocol. Mechanism studies indicate molecular oxygen is the terminal oxidant and the O-source of the oxiranes.

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通过共轭烯烃环氧化作用和 BHT 羟基化作用，用分子氧对缺电子烯烃进行化学选择性环氧化作用

据报道，在富电子烯分子存在的情况下，可以对缺电子烯烃进行化学选择性环氧化。这种化学选择性环氧化策略经过共轭烯烃环氧化和 BHT 羟基化过程，高产率地得到各种有用的环氧乙烷，尤其是 2-取代的 2-三氟甲基环氧乙烷。重要的是，该方案条件温和，不含过渡金属，操作简单，可按克级放大，并可容忍不同的官能团。候选药物 HSD-16 可通过该方案顺利合成。机理研究表明，分子氧是环氧乙烷的终端氧化剂和 O-源。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Science China Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

14.40

自引率

7.30%

发文量

3787

审稿时长

2.2 months

期刊介绍： Science China Chemistry, co-sponsored by the Chinese Academy of Sciences and the National Natural Science Foundation of China and published by Science China Press, publishes high-quality original research in both basic and applied chemistry. Indexed by Science Citation Index, it is a premier academic journal in the field. Categories of articles include: Highlights. Brief summaries and scholarly comments on recent research achievements in any field of chemistry. Perspectives. Concise reports on thelatest chemistry trends of interest to scientists worldwide, including discussions of research breakthroughs and interpretations of important science and funding policies. Reviews. In-depth summaries of representative results and achievements of the past 5–10 years in selected topics based on or closely related to the research expertise of the authors, providing a thorough assessment of the significance, current status, and future research directions of the field.