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A Practical Flow Synthesis of 1,2,3-Triazoles

A Practical Flow Synthesis of 1,2,3-Triazoles
A Practical Flow Synthesis of 1,2,3-Triazoles
A robust and versatile protocol for synthesis of 1-monosubstituted and 1,4-disubstituted 1H-1,2,3-triazoles was established under continuous flow conditions using copper-on-charcoal as a heterogeneous catalyst. This methodology allowed for the synthesis of a diverse set of substituted 1,2,3-triazoles with good functional group tolerance and high yields. 2-Ynoic acids were also used as small-chain alkyne donors in a decarboxylation/cycloaddition cascade, allowing gaseous reagents to be bypassed, delivering desired triazoles in high yields. The developed methodology was used to synthesize an antiepileptic agent, rufinamide, which was obtained in 96% isolated yield.
Flow Chemistry, catalysis, Click reaction, triazoles
2046-2069
28910-28915
Drelinkiewicz, Dawid
fee337f9-b562-4542-a9f2-6a5c583ebc7d
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b
Drelinkiewicz, Dawid
fee337f9-b562-4542-a9f2-6a5c583ebc7d
Whitby, Richard J.
45632236-ab00-4ad0-a02d-6209043e818b

Drelinkiewicz, Dawid and Whitby, Richard J. (2022) A Practical Flow Synthesis of 1,2,3-Triazoles. RSC Advances, 12 (45), 28910-28915. (doi:10.1039/d2ra04727f).

Record type: Article

Abstract

A robust and versatile protocol for synthesis of 1-monosubstituted and 1,4-disubstituted 1H-1,2,3-triazoles was established under continuous flow conditions using copper-on-charcoal as a heterogeneous catalyst. This methodology allowed for the synthesis of a diverse set of substituted 1,2,3-triazoles with good functional group tolerance and high yields. 2-Ynoic acids were also used as small-chain alkyne donors in a decarboxylation/cycloaddition cascade, allowing gaseous reagents to be bypassed, delivering desired triazoles in high yields. The developed methodology was used to synthesize an antiepileptic agent, rufinamide, which was obtained in 96% isolated yield.

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Accepted/In Press date: 1 October 2022
Published date: 11 October 2022
Additional Information: This journal is © The Royal Society of Chemistry.
Keywords: Flow Chemistry, catalysis, Click reaction, triazoles

Identifiers

Local EPrints ID: 471513
URI: http://eprints.soton.ac.uk/id/eprint/471513
ISSN: 2046-2069
PURE UUID: 047db42c-52d3-4b93-85d1-bd46a8132ca7
ORCID for Dawid Drelinkiewicz: ORCID iD orcid.org/0000-0002-7181-8366
ORCID for Richard J. Whitby: ORCID iD orcid.org/0000-0002-9891-5502

Catalogue record

Date deposited: 09 Nov 2022 18:18
Last modified: 10 Nov 2022 02:55

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Contributors

Author: Dawid Drelinkiewicz ORCID iD

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