One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides

被引:32
|
作者
Ladouceur, Sebastien [1 ]
Soliman, Ahmed M. [1 ]
Zysman-Colman, Eli [1 ]
机构
[1] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada
来源
SYNTHESIS-STUTTGART | 2011年 / 22期
基金
加拿大自然科学与工程研究理事会;
关键词
click chemistry; Huisgen cycloaddition; triazoles; alkynes; azides; RHENIUM TRICARBONYL COMPLEXES; SITU GENERATED AZIDES; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES; TERMINAL ALKYNES; 1,3-DIPOLAR CYCLOADDITIONS; REGIOSELECTIVE SYNTHESIS; RUTHENIUM(II) COMPLEXES; IRIDIUM(III) COMPLEXES; COUPLING REACTION; LIGANDS;
D O I
10.1055/s-0030-1260256
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes.
引用
收藏
页码:3604 / 3611
页数:8
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