使用芳基重氮盐和可见光对吡啶进行光芳基化反应：一种电子给体-受体方法
Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach.
作者信息
Bartolomeu Aloisio de A, Silva Rodrigo C, Brocksom Timothy J, Noël Timothy, de Oliveira Kleber T
机构信息
Departamento de Química , Universidade Federal de São Carlos , São Carlos , São Paulo 13565-905 , Brazil.
Department of Chemical Engineering and Chemistry, Sustainable Process Engineering, Micro Flow Chemistry & Synthetic Methodology , Eindhoven University of Technology , De Rondom 70 (Helix, STO 1.37) , 5612 AP Eindhoven , The Netherlands.
出版信息
J Org Chem. 2019 Aug 16;84(16):10459-10471. doi: 10.1021/acs.joc.9b01879. Epub 2019 Aug 1.
A metal-free methodology for the photoarylation of pyridines, in water, is described giving 2 and 4-arylated-pyridines in yields up to 96%. The scope of the aryldiazonium salts is presented showing important results depending on the nature and position of the substituent group in the diazonium salt, that is, electron-donating or electron-withdrawing in the , , or positions. Further heteroaromatics were also successfully photoarylated. Mechanistic studies and comparison between our methodology and similar metal-catalyzed procedures are presented, suggesting the occurrence of a visible-light EDA complex which generates the aryl radical with no need for an additional photocatalyst.
本文描述了一种在水中进行吡啶光芳基化的无金属方法，可得到产率高达96%的2-芳基吡啶和4-芳基吡啶。文中展示了芳基重氮盐的适用范围，结果表明，根据重氮盐中取代基的性质和位置（即供电子或吸电子基团处于邻位、间位或对位）会产生重要影响。其他杂芳烃也成功实现了光芳基化。文中还介绍了机理研究以及我们的方法与类似金属催化方法的比较，结果表明存在一种可见光激发的电子给体-受体（EDA）络合物，该络合物可生成芳基自由基，无需额外的光催化剂。
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