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

31 October 2023, Version 1
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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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
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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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