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Strain-promoted azide-alkyne cycloaddition enhanced by the secondary interactions

29 October 2024, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Azide-alkyne cycloaddition of cyclooct-2-yn-1-ol and 2-(azidophenyl)boronic acid proceeded rapidly at room temperature with complete regioselectivity to afford a triazole having a boronate ester group. The secondary covalent interaction of the boronate ester contributed to the rate acceleration and the control of regioselectivity. The interaction of an imine was also evaluated.

Keywords

Azide
alkyne
cycloaddition
cyclooctyne
boronate ester
imine
secondary interaction

Supplementary materials

Title
Description
Actions
Title
The supporting imformation
Description
Experimental procedures, 1H and 13C NMR spectra of new compounds
Actions

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Version History

Oct 29, 2024 Version 1

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License

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The content is available under CC BY 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2024-jjg4n
D O I: 10.26434/chemrxiv-2024-jjg4n [opens in a new tab]

Funding

Japan Society for the Promotion of Science
22K06500

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) declare that they have sought and gained approval from the relevant ethics committee/IRB for this research and its publication.

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