Dr. Vinh X. Truong and Dr. Andrew P. Dove Organocatalytic, Regioselective Nucleophilic “Click” Addition of Thiols to Propiolic Acid Esters for Polymer–Polymer Coupling Angewandte Chemie International Edition 52
Discerning Tastes: The regioselectivity of the nucleophilic addition of thiols to electron-deficient alkynes is controlled by the choice of the solvent (i.e. the polarity of the reaction mixture) and the catalyst. Both thioalkenes and dithianes can be prepared in a rapid reaction that generates no by-products (see scheme). In turn the utility of this reaction is shown for efficient end-group modification of polymers.
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