Easy preparation of 1,4,5-trisubstituted 5-(2-alkoxy-1,2-dioxoethyl)-1,2,3-triazoles by chemoselective trapping of copper(I)-carbon bond with alkoxalyl chloride

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• 作者：Bo Wang ; Muhammad Naeem Ahmed ; Jianlan Zhang ; Wenwen Chen ; Xinyan Wang ; Yuefei Hu
• 关键词：1-Copper(I)-alkynes ; Cu-C bond ; Click chemistry ; Triazoles ; Acylation
• 刊名：Tetrahedron Letters
• 出版年：2013
• 出版时间：6 November, 2013
• 年：2013
• 卷：54
• 期：45
• 页码：6097-6100
• 全文大小：854 K

文摘

We found that alkoxalyl chloride (ClCOCO₂R) did not carry out an acylation on 1-copper(I) alkyne in solvent without additives, but chemoselectively on 5-copper(I) 1,2,3-triazole (an intermediate in cycloaddition of 1-copper(I) alkyne and azide). Thus, a one-pot preparation of 1,4,5-trisubstituted 5-(2-alkoxy-1,2-dioxoethyl)-1,2,3-triazole was achieved by simply stirring the mixture of 1-copper(I) alkyne, azide, and alkoxalyl chloride at room temperature for 4 h.