Thiolate-CLPG (chemiluminescent protecting groups) based on coumaranone thiolcarbamates

Tim Lippold; Julia Kosolapova; Niko T. Flosbach; Robert Herzhoff; Axel G. Griesbeck; Mathias Wickleder

doi:10.1039/D4CC06150K

Thiolate-CLPG (chemiluminescent protecting groups) based on coumaranone thiolcarbamates†

Tim Lippold,

*^a Julia Kosolapova,^b Niko T. Flosbach,^b Robert Herzhoff,^c Axel G. Griesbeck

*^a and Mathias Wickleder

Author affiliations

* Corresponding authors

^a Faculty of Mathematics and Natural Sciences, Department of Chemistry and Biochemistry, Institute of Organic Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany
E-mail: griesbeck@uni-koeln.de
Fax: +49-221-4701166

^b Faculty of Mathematics and Natural Sciences, Department of Chemistry and Biochemistry, Institute of Inorganic and Materials Chemistry, University of Cologne, Greinstr. 6, 50939 Köln, Germany

^c Faculty of Mathematics and Natural Sciences, Department of Chemistry and Biochemistry, Institute of Light and Materials, University of Cologne, Greinstr. 4-6, 50939 Köln, Germany

Abstract

The base-induced oxidative release of aromatic and aliphatic thiols from novel coumaranone-thiolurethanes 3a–3e is accompanied by long-lasting blue or green chemiluminescence. Thus, these compounds serve as base/oxidation-labile protecting groups that decompose with strong visible luminescence and subsequent quantitative release of the protected thiolate as leaving group.

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Article information

DOI: https://doi.org/10.1039/D4CC06150K
Article type: Communication
Submitted: 19 Nov 2024
Accepted: 24 Jan 2025
First published: 25 Jan 2025
This article is Open Access

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Chem. Commun., 2025,61, 4792-4795

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Thiolate-CLPG (chemiluminescent protecting groups) based on coumaranone thiolcarbamates

T. Lippold, J. Kosolapova, N. T. Flosbach, R. Herzhoff, A. G. Griesbeck and M. Wickleder, Chem. Commun., 2025, 61, 4792 DOI: 10.1039/D4CC06150K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Communications

Thiolate-CLPG (chemiluminescent protecting groups) based on coumaranone thiolcarbamates†

Abstract

Supplementary files

Article information

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Thiolate-CLPG (chemiluminescent protecting groups) based on coumaranone thiolcarbamates

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