Categories: C-S Bond Formation >
Synthesis of alkynyl sulfides
Recent Literature
A mild, rapid, and selective copper-catalyzed Csp-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.
