通过一级卤代烷和叠氮化钠的串联一锅法钌催化的叠氮化物-炔烃环加成反应。

Sequential one-pot ruthenium-catalyzed azide-alkyne cycloaddition from primary alkyl halides and sodium azide.

机构信息

Division of Chemistry and Biochemistry, Department of Chemical and Biological Engineering, Chalmers University of Technology, SE-41296 Gothenburg, Sweden.

出版信息

J Org Chem. 2011 Apr 1;76(7):2355-9. doi: 10.1021/jo200134a. Epub 2011 Mar 9.

DOI:10.1021/jo200134a

PMID:21388208

Abstract

An experimentally simple sequential one-pot RuAAC reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields starting from an alkyl halide, sodium azide, and an alkyne, is reported. The organic azide is formed in situ by treating the primary alkyl halide with sodium azide in DMA under microwave heating. Subsequent addition of [RuClCp*(PPh(3))(2)] and the alkyne yielded the desired cycloaddition product after further microwave irradiation.

摘要

报道了一种实验操作简单的连续一锅 RuAAC 反应，以卤代烷烃、叠氮化钠和炔烃为起始原料，可高产率地得到 1,5-二取代的 1H-1,2,3-三唑。通过在微波加热下用叠氮化钠处理一级卤代烷烃，在 DMA 中就地生成有机叠氮化物。随后加入[RuClCp*(PPh(3))(2)]和炔烃，进一步微波辐射后得到所需的环加成产物。