Azide-alkyne cycloaddition (click) reaction in biomass-derived solvent CyreneTM under one-pot conditions

Zoltán Medgyesi; László T. Mika

doi:10.3762/bxiv.2025.21.v1

Azide-alkyne cycloaddition (click) reaction in biomass-derived solvent Cyrene^TM under one-pot conditions

Zoltán Medgyesi and
László T. Mika

Submitting author affiliation:

Department of Chemical and Environmental Process Engineering, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Budapest, Hungary

Beilstein Arch. 2025, 202521. https://doi.org/10.3762/bxiv.2025.21.v1

Published 02 Apr 2025

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SUBJECT AREAS

Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

Abstract

It was demonstrated that Cyrene^TM as a biomass-originated polar aprotic solvent could be utilized as an alternative reaction medium for copper(I)-catalyzed azide-alkyne cycloaddition (click or CuAAC) reaction, for the synthesis of various 1,2,3-triazoles under mild conditions. Nineteen products involving N-substituted-4-phenyl-1H-1,2,3- and 1-allyl-4-substituted-1H-1,2,3-triazoles were synthesized under one-pot conditions and isolated with good to excellent yields (50–96%) and purity (>98%). The observed results represent an example that proves that biomass-derived safer solvents can be introduced into a synthetically important transformation exhibiting higher chemical and environmental safety.

Keywords: Cyrene; click chemistry; cycloaddition; alternative solvent, 1,2,3-triazols

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Medgyesi, Z.; Mika, L. T. Beilstein Arch. 2025, 202521. doi:10.3762/bxiv.2025.21.v1

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)