Synthesis of 2-Azidomethyl-5-ethynylfuran

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.

Reference: Synthesis, 2019, ASAP

DOI: 10.1055/s-0037-1610414

On-line version: https://www.thieme-connect.com/products/ejournals/html/10.1055/s-0037-1610414