Department of Chemistry and Biochemistry , Florida State University , 95 Chieftan Way , Tallahassee , Florida 32306-4390 , United States.
J Org Chem. 2018 May 4;83(9):5092-5103. doi: 10.1021/acs.joc.8b00424. Epub 2018 Apr 13.
A new method to convert terminal alkynes under relatively mild conditions to 1-cyanoalkynes using in situ formed cyanogen is described. 1-Cyanoalkynes have a higher reactivity than terminal alkynes in the ruthenium(II)-catalyzed regiospecific azide-alkyne cycloaddition to afford 4-cyano-1,2,3-triazoles. A mechanistic proposal different from the one that terminal alkynes adopt under the same reaction conditions is proposed. This work provides a new and convenient two-step sequence to prepare 4-cyano-1,2,3-triazoles from terminal alkynes and organic azides.
本文描述了一种在相对温和条件下将末端炔烃原位转化为氰基炔的新方法。在钌（II）催化的区域选择性叠氮-炔环加成反应中，1-氰基炔的反应活性高于末端炔烃，可得到 4-氰基-1,2,3-三唑。提出了一种与在相同反应条件下末端炔烃采用的机理不同的机理假设。这项工作提供了一种从末端炔烃和有机叠氮化物制备 4-氰基-1,2,3-三唑的新的、方便的两步序列。
