Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 236, Issue -, Pages -Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2020.109516
Keywords
1-Aryl-4-(trimethylsilyl)-1H-1,2,3-triazole; 1-Aryl-4-iodo-1,2,3-triazole; Trifluoromethylation; Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate; Tetrabutylammonium iodide; 1-Aryl-4-(trifluoromethyl)-1H-1, 2, 3-triazole
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While several methods are available for the synthesis of a host of trifluoromethylated heterocycles, very few of them have been applied to access 4-trifluoromethylated 1,2,3-triazoles. We report herein a general methodology for the trifluoromethylation of 1-aryl-4-iodo-1, 2, 3-triazoles. Tetrabutylammonium iodide (TBAI) has been shown to provide enhanced conversion in these CuI-mediated reaction using methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA). The method exhibited broad functional group tolerance and was applied to the synthesis of a library of 1-aryl-4-trifluoromethyl-1,2,3-triazoles on the multi-gram scale.
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