Sequential Seyferth-Gilbert/CuAAC Reactions: Application to the One-Pot Synthesis of Triazoles from Aldehydes

Delphine Luvino, Camille Amalric, Michael Smietana*, Jean-Jacques Vasseur*

*Institut des Biomolécules Max Mousseron, UMR 5247 CNRS-UMI-UMII, Université Montpellier II, Place Eugène Bataillon, 34095 Montpellier, France, Email: msmietanauniv-montp2.fr, vasseuruniv-montp2.fr

D. Luvino, C. Amalric, M. Smietana, J.-J. Vasseur, Synlett, 2007, 3037-3041.

DOI: 10.1055/s-2007-990877

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Abstract

A reliable and operationally simple one-pot reaction for a one-carbon homologation of various aldehydes followed by Cu-catalyzed azide-alkyne click chemistry gives 1,4-disubstituted 1,2,3-triazoles in good yields without the need for isolation of the alkyne intermediates.

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Key Words

click chemistry, 1,2,3-triazoles, Bestmann-Ohira reagent, Seyferth-Gilbert homologation, bioconjugation

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ID: J60-Y2007-3860