School of Chemistry and Chemical Engineering, South China University of Technology , Guangzhou 510640, China.
J Org Chem. 2016 Nov 18;81(22):11461-11466. doi: 10.1021/acs.joc.6b02124. Epub 2016 Nov 3.
A new strategy for thiazoles via copper-catalyzed [3+1+1]-type condensation reaction from oximes, anhydrides and potassiumthiocyanate (KSCN) is developed herein. The transformation has good functional group tolerance and various thiazoles were formed smoothly in good to excellent yields under mild reaction conditions. This process involves copper-catalyzed N-O/C-S bond cleavages, activation of vinyl sp C-H bond, and C-S/C-N bond formations which are under redox-neutral conditions as well as operational simplicity.
本文开发了一种通过肟、酸酐和硫氰酸钾（KSCN）的铜催化[3+1+1]型缩合反应合成噻唑的新策略。该转化具有良好的官能团容忍性，在温和的反应条件下，各种噻唑都能以良好到优秀的产率顺利合成。该过程涉及铜催化的 N-O/C-S 键断裂、乙烯基 sp^C-H 键的活化以及 C-S/C-N 键的形成，这些过程在氧化还原中性条件下进行，操作简单。
