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Synthesis of Thioxanthone 10,10-Dioxides and Sulfone-Fluoresceins via Pd-Catalyzed Sulfonylative Homocoupling

Gergely Knorr, Mariano L. Bossi, Alexey N. Butkevich, Stefan W. Hell

2024Organic Letters10 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide Our report describes the facile and scalable preparation of 9 H -thioxanthen-9-one 10,10-dioxides via Pd-catalyzed sulfonylative homocoupling of the appropriately substituted benzophenones. This transformation provides a straightforward route 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.

Topics & Concepts

SulfoneThioxanthoneChemistryCatalysisCombinatorial chemistryFluorescencePhotochemistryOrganic chemistryPhotopolymerQuantum mechanicsPhysicsPolymerPolymerizationSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
Synthesis of Thioxanthone 10,10-Dioxides and Sulfone-Fluoresceins via Pd-Catalyzed Sulfonylative Homocoupling | Litcius