Alkynyl sulfides are prevalent in bioactive molecules and functional materials. A variety of methods for the construction of alkynyl sulfides have been developed, however, the general and practical synthetic strategy to afford alkynyl sulfides from readily available starting materials remains non-trivial. Herein, we report that the widely accessible 1,2,3-thiadiazoles as robust alkynylthiolate anions, which couple with C(sp1-3)-electrophiles to construct corresponding alkynyl sulfides in the presence of metal catalyst or under metal free conditions (79 examples with average 68% yield). The alkynylthiolation reaction with aryl iodides and bromoalkynes is experimentally easy to conduct under mild conditions in the presence of palladium or copper catalysts; the alkynylthiolation with 1o-, 2o-alkyl electrophiles and difluorocarbene precursor are performed under metal free conditions. Gram-scale reactions and diverse synthetic transformations convincingly demonstrate the synthetic potential of this method.

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