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CC BY ND NC 4.0 · Synthesis 2019; 51(05): 1235-1242
DOI: 10.1055/s-0037-1610414
DOI: 10.1055/s-0037-1610414
paper
Synthesis of 2-Azidomethyl-5-ethynylfuran: A New Bio-Derived Self-Clickable Building Block
Authors
This study was supported by a Russian Science Foundation 17-13-01176 grant.
Further Information
Publication History
Received: 05 October 2018
Accepted after revision: 26 November 2018
Publication Date:
08 January 2019 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610414.
- Supporting Information (PDF)
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