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Synthesis of 1-Fluoroalkyl-5-Substituted-1,2,3-Triazoles from Carbonyl-Stabilized Phosphonium Ylides

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide A mild, rapid, and regioselective cyclization of azidofluoroalkanes with carbonyl-stabilized phosphonium ylides, resulting in the formation of 1-fluoroalkyl-5-substituted-1,2,3-triazoles, is presented. The synthetic method tolerates air and water, works at room temperature in a benign solvent, and is metal-free. Both starting materials are commercially available and easily prepared. The cyclization method was expanded to 4-halogen-substituted analogues of target triazoles, which underwent either rhodium-catalyzed transannulation with benzonitrile to yield uniquely substituted N -fluoroalkylated 4-haloimidazoles or cross-coupling reactions to produce fully substituted N -fluoroalkylated triazoles.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c01055

Authors: David Tichý, Tomáš Černý, Josef Filgas, Svatava Voltrová, Blanka Klepetářová, Petr Beier