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Synthesis of thioxanthone 10,10-dioxides and sulfone-fluoresceins via Pd-catalyzed sulfonylative homocoupling

31 October 2023, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Our report describes the facile and scalable preparation of 9H-thioxanthen-9-one 10,10-dioxides via Pd-catalyzed sulfonylative homocoupling of the appropriately substituted benzophenones. This transformation provides a straightforward entry to previously unreported sulfone-fluoresceins and -fluorones. Several examples of these red-fluorescent dyes have been prepared, characterized and evaluated as live-cell permeant labels compatible with super-resolution fluorescence microscopy with 775 nm stimulated emission depletion.

Keywords

Pd catalysis
fluorescent dyes
fluorescence microscopy
STED
HaloTag
sulfones

Supplementary materials

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Description
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Supplementary information
Description
Additional experimental details, materials, methods, and char-acterization data for all new compounds, including Figures S1-S5 and Tables S1-S2; NMR spectra
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Supplementary video
Description
Supplementary Video S1: confocal time-lapse video of living U2OS cells stably expressing vimentin-HaloTag fusion protein labeled with the probe 7a-Halo
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Version History

Oct 31, 2023 Version 1

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

DOI

10.26434/chemrxiv-2023-pr52z
D O I: 10.26434/chemrxiv-2023-pr52z [opens in a new tab]

Funding

Bundesministerium für Bildung und Forschung (German Federal Ministry of Education and Research)
13N14122

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) have declared ethics committee/IRB approval is not relevant to this content

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