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无催化剂和添加剂条件下可见光诱导合成3-烷基色酮

Visible-Light-Induced Synthesis of 3-Alkyl Chromones under Catalyst- and Additive-Free Conditions.

作者信息

Zhao Wei, He Zhiqin, Yang Xiaohui, Yu Yang, Baell Jonathan B, Huang Fei

机构信息

School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023, P. R. China.

School of Environmental Science and Engineering, Nanjing Tech University, Nanjing 211816, P. R. China.

出版信息

J Org Chem. 2023 Oct 6;88(19):13634-13644. doi: 10.1021/acs.joc.3c01339. Epub 2023 Sep 7.

Abstract

Herein, we reported an efficient and facile visible-light-induced 3-alkyl chromone synthesis from easily accessible -hydroxyaryl enaminones and α-diazo esters. In this protocol, excellent yields were obtained with a broad substrate scope at room temperature, tolerating various functional groups. Of note is that this eco-friendly methodology features catalyst- and additive-free, mild reaction conditions, simple operation procedure, and easy scale-up, which affords a convenient pathway for the preparation of 3-alkyl chromones. Experimental results and density functional theory (DFT) computation analyses confirm the participation of carbene species and active cyclopropane intermediate.

摘要

在此,我们报道了一种高效简便的可见光诱导的3-烷基色酮合成方法,该方法以易于获得的β-羟基芳基烯胺酮和α-重氮酯为原料。在此反应体系中,在室温下能以较宽的底物范围获得优异的产率,且能耐受各种官能团。值得注意的是,这种环境友好型方法具有无需催化剂和添加剂、反应条件温和、操作步骤简单以及易于放大等特点,为3-烷基色酮的制备提供了一条便捷途径。实验结果和密度泛函理论(DFT)计算分析证实了卡宾物种和活性环丙烷中间体的参与。

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