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Standardized Approach for Diversification of Complex Small Molecules via Aryl Thianthrenium Salts

Dilgam Ahmadli, Sven Müller, Yuanhao Xie, Tomáš Šmejkal, Simon Jaeckh, Andrei V. Iosub, Simon R. Williams, Tobias Ritter

2025Journal of the American Chemical Society36 citationsDOIOpen Access PDF

Abstract

Thianthrenation is a useful strategy for the late-stage diversification of complex small molecules owing to the positional selectivity and the synthetic versatility of thianthrenium salts as electrophilic linchpins. However, substrate-dependent identification of suitable reaction conditions for thianthrenation can be difficult. Reported reaction conditions for the functionalization of thianthrenium salts vary significantly and, in some instances, lack robustness and practicality. Herein, we report a generalized approach for the preparation of thianthrenium salts and two reaction manifolds for practical, robust, and parallel diversification of thianthrenium salts.

Topics & Concepts

ChemistryArylDiversification (marketing strategy)MoleculeSmall moleculeCombinatorial chemistryComputational chemistryOrganic chemistryBiochemistryBusinessAlkylMarketingCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsRadical Photochemical Reactions
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