Synthesis of 2-Azidomethyl-5-ethynylfuran: A New Bio-Derived Self-Clickable Building Block

Bogdan Ya. Karlinskii; Leonid V. Romashov; Konstantin I. Galkin; Pavel G. Kislitsyn; Valentine P. Ananikov

doi:10.1055/s-0037-1610414

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(05): 1235-1242
DOI: 10.1055/s-0037-1610414

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Synthesis of 2-Azidomethyl-5-ethynylfuran: A New Bio-Derived Self-Clickable Building Block

Authors

Bogdan Ya. Karlinskii
Leonid V. Romashov
Konstantin I. Galkin
Pavel G. Kislitsyn
Valentine P. Ananikov *

N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prospect 47, Moscow, 119991, Russian Federation Email: val@ioc.ac.ru

Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

2-Azidomethyl-5-ethynylfuran, a new ambivalent compound with both azide and alkyne moieties that can be used as a self-clickable monomer, is synthesized starting directly from renewable biomass. The reactivity of the azide group linked to furfural is tested via the efficient preparation of a broad range of furfural-containing triazoles in good to excellent yields using a ‘green’ copper(I)-catalyzed azide–alkyne cycloaddition procedure. Access to new bio-based chemicals and oligomeric materials via a click-chemistry approach is also demonstrated using this bio-derived building block.

Key words

5-(hydroxymethyl)furfural - click chemistry - biomass conversion - triazoles - oligomers

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References

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