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Synthesis 2015; 47(24): 3936-3946
DOI: 10.1055/s-0035-1560352
DOI: 10.1055/s-0035-1560352
paper
Synthesis of Fluorinated 1,4,5-Substituted 1,2,3-Triazoles by RuAAC Reaction
Further Information
Publication History
Received: 06 August 2015
Accepted after revision: 09 September 2015
Publication Date:
02 October 2015 (online)
Abstract
Herein, 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 1H, 13C, and 19F 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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560352.
- Supporting Information
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