Year: 2026
Type: preprint
Abstract: A multigram synthetic approach to alkenyl azides based on copper-catalyzed azidodeboronation of alkenyl pinacol boronates was described. The optimized protocol relied on the use of Cu(OAc) 2 as the reaction promoter, which provided higher, reproducible yields and did not cause uncontrolled decomposition of the reaction mixture, unlike the CuSO 4 ·5H 2 O-based protocol reported previously. The method was applicable to β-, β,β-, and α,β-substituted substrates, including those bearing electron-withdrawing groups and saturated O -, N -, and S -heterocyclic motifs. Some alkenyl azides were prepared on up to 21 g scale, and their thermal behavior was evaluated by thermogravimetric analysis. The synthetic utility of the products was demonstrated through the preparation of a substituted pyrrole and 1-alkenyl-1,2,3-triazoles. Furthermore, a one-pot azidation – click reaction protocol enabled the direct conversion of alkenyl boronates into the corresponding triazoles without isolation of unstable or highly volatile alkenyl azide intermediates, thereby broadening the accessible substrate scope.
Source: ChemRxiv
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7215081095