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Synthesis of alkynyl sulfides

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Alkynylation of thiols using ethynyl benziodoxolone (EBX) hypervalent iodine reagents enables the synthesis of aryl- and alkyl-substituted alkynes containing a broad range of functional groups. New sulfur nucleophiles such as thioglycosides, thioacids, and sodium hydrogen sulfide were also alkynylated successfully to lead to a general and practical method for the synthesis of thioalkynes.
R. Frei, M. D. Wodrich, D. P. Hari, P.-A. Borin, C. Chauvier, J. Waser, J. Am. Chem. Soc., 2014, 136, 16563-16573.


S-Alkyl, S-aryl, and S-vinyl thiosulfate sodium salts (Bunte salts), which can readily be prepared from sodium thiosulfate, react with Grignard reagents to give sulfides in good yields. The reaction is amenable to a broad structural array of Bunte salts and Grignard reagents. Importantly, this route to sulfides avoids the use of malodorous thiol starting materials or byproducts.
J. T. Reeves, K. Camara, Z. S. Han, Y. Xu, H. Lee, C. A. Busacca, C. H. Senanayaka, Org. Lett., 2014, 16, 1196-1199.