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Synthesis of alkynyl sulfides

Recent Literature

A mild, rapid, and selective copper-catalyzed C_sp-S cross-coupling of thiols and bromoalkynes provides a broad range of alkynyl sulfides, including difficult-to-access bis-heteroatom-functionalized (S,S-, S,P-, and S,N-) alkynes.
E. Godin, J. Santandrea, A. Caron, S. K. Collins, Org. Lett., 2020, 22, 5905-5909.

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.

A mild and odorless copper-catalyzed thiolation of terminal alkynes with thiosulfonates provides convenient access to a wide variety of alkynyl sulfides and sulfur-containing heterocycles via a subsequent iodocyclization.
K. Kanemoto, S. Yoshida, T. Hosoya, Org. Lett., 2019, 21, 3172-3177.

The use of β-sulfinylesters as versatile sulfur source enables direct C(sp)-, C(sp²)-, and C(sp³)-H thiolation reactions. The desired products are formed via chemoselective retro-Michael C-S bond cleavage of sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters.
Y. Chen, S. Wen, Q. Tian, Y. Zhang, G. Cheng, Org. Lett., 2021, 23, 7905-7909.

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.

Related

N-Alkynylthio phthalimides can be easily prepared in three steps from commercially available phthalimide and silver acetylides. N-Alkynylthio phthalimides are efficient electrophilic alkynylthiolating reagents that can react with various C-nucleophiles, including β-ketoesters, aryl boronic acids, and Grignard reagents to afford a diverse range of alkynyl thioethers under mild conditions.
W.-C. Gao, Y.-Z. Shang, H.-H. Chang, X. Li, W.-L. Wei, X.-Z. Yu, R. Zhou, Org. Lett., 2019, 21, 6021-6024.

N-Alkynylthio phthalimides can be easily prepared in three steps from commercially available phthalimide and silver acetylides. N-Alkynylthio phthalimides are efficient electrophilic alkynylthiolating reagents that can react with various C-nucleophiles, including β-ketoesters, aryl boronic acids, and Grignard reagents to afford a diverse range of alkynyl thioethers under mild conditions.
W.-C. Gao, Y.-Z. Shang, H.-H. Chang, X. Li, W.-L. Wei, X.-Z. Yu, R. Zhou, Org. Lett., 2019, 21, 6021-6024.