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

,
Leonid V. Romashov
,
Konstantin I. Galkin
,
Pavel G. Kislitsyn
,
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
› Author Affiliations
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 (eFirst)

  

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

 
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