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Synthesis of Fluorinated 1,4,5-Substituted 1,2,3-Triazoles by RuAAC Reaction
Alternative Title用RuAAC反应合成含氟的1,4,5-取代-1,2,3-三唑
Shen Q(沈倩)1; Han EJ(韩恩健)1; Huang YG(黄焰根)1; Chen QY(陈庆云)1; Guo Y(郭勇)1
Source PublicationSynthesis
AbstractHerein, we report a convenient methodology for the synthesis of fluorinated 1,4,5-substituted 1,2,3-triazoles. The azide-alkyne cycloaddition reaction of internal alkynes catalyzed by a ruthenium complex efficiently afforded 2,2,2-trifluoroethyl- and (trifluoromethyl)thio-substituted 1,2,3-triazoles. Two types of internal alkyne, 1-aryl-2-(2,2,2-trifluoroethyl)acetylenes and 1-aryl-2-[(trifluoromethyl)thio]acetylenes, were used. This ruthenium-catalyzed azide-alkyne cycloaddition reaction was highly regioselective giving 4-aryl-5-(2,2,2-trifluoroethyl)- or 4-aryl-5-[(trifluoromethyl)thio]-1H-1,2,3-triazoles. Various functionalities were tolerated in the alkyl and aryl azides by this Huisgen 1,3-dipolar cycloaddition. All the triazoles were characterized by H-1, C-13, and F-19 NMR, IR, and HRMS (or elemental analysis). Several triazoles were characterized by single-crystal X-ray structural analysis to confirm the regioselectivity of 1,2,3-triazole formation.
Subject Area氟化学
Indexed BySCI
WOS IDWOS:000366209800013
Citation statistics
Document Type期刊论文
Corresponding AuthorHuang YG(黄焰根); Chen QY(陈庆云); Guo Y(郭勇)
2.中科院上海有机化学研究所, 有机氟化学重点实验室
Recommended Citation
GB/T 7714
Shen Q,Han EJ,Huang YG,et al. Synthesis of Fluorinated 1,4,5-Substituted 1,2,3-Triazoles by RuAAC Reaction[J]. Synthesis,2015,47(24):3936-3946.
APA 沈倩,韩恩健,黄焰根,陈庆云,&郭勇.(2015).Synthesis of Fluorinated 1,4,5-Substituted 1,2,3-Triazoles by RuAAC Reaction.Synthesis,47(24),3936-3946.
MLA 沈倩,et al."Synthesis of Fluorinated 1,4,5-Substituted 1,2,3-Triazoles by RuAAC Reaction".Synthesis 47.24(2015):3936-3946.
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