Organocatalytic, Regioselective Nucleophilic “Click” Addition of Thiols to Propiolic Acid Esters for Polymer–Polymer Coupling


  • The authors are grateful to the BBSRC (BB/I002286/1) for funding a postdoctoral fellowship (V.X.T.). The SEC equipment used in this research was obtained through Birmingham Science City: Innovative Uses for Advanced Materials in the Modern World (West Midlands Centre for Advanced Materials Project 2), with support from Advantage West Midlands (AWM) and partly funded by the European Regional Development Fund (ERDF).


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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.