Categories: C-S Bond Formation >
Synthesis of vinyl sulfides
Recent Literature
A simple and efficient protocol for the cross-coupling of vinyl halides with
thiols catalyzed by recyclable CuO nanoparticles under ligand-free conditions
allows the synthesis of a various vinyl sulfides in excellent yields with
retention of stereochemistry.
V. P. Reddy, K. Swapna, A. V. Kumar, K. R. Rao, Synlett, 2009,
2777-2782.
A mild, versatile, palladium-free method for the synthesis of vinyl sulfides
using the soluble copper(I) catalyst [Cu(phen)(PPh3)2]NO3
is reported. The desired vinyl sulfides are obtained with retention of
stereochemistry in good to excellent yields.
C. G. Bates, P. Saejueng, M. Q. Doherty, D. Venkataraman, Org. Lett., 2004, 6, 5005-5008.
cis-1,2-Cyclohexanediol is an efficient and versatile bidentate O-donor
ligand that provides a highly active Cu-catalytic system for cross-coupling
reactions of alkyl, aryl, or heterocyclic thiols with either alkyl, aryl,
heterocyclic, or substituted vinyl halides. This new catalytic system promoted
the mild and efficient stereo- and regiospecific synthesis of biologically
important vinyl sulfides.
M. S. Kabir, M. Lorenz, M. L. V. Linn, O. A. Namjoshi, S. Ara, J. M. Cook, J. Org. Chem., 2010,
75, 3626-3643.
Indium tri(organothiolate) derivatives are effective nucleophilic coupling
partners in Pd-catalyzed C-S crosscoupling reactions to produce functionalized
sulfides in excellent yields with high atom efficiency and complete regio- and
chemoselectivity.
J.-Y. Lee, P. H. Lee, J. Org. Chem., 2008,
73, 7413-7416.
The coupling of vinyl bromides with thiols or diphenyl diselenide using copper(I)
salts as catalysts in ionic liquids based on amino acids gives vinyl
chalcogenides in good to excellent yields with retention of stereochemistry. The
ionic liquids act as solvent, base, and excellent promoter for the
copper-catalyzed coupling reactions.
Z. Wang, H. Mo, W. Bao, Synlett, 2007, 91-94.
With CuI as the catalyst and K3PO4 • 3 H2O as
the base, a highly efficient, ligand-free intramolecular S-vinylation of thiols
with vinyl chlorides or bromides was successfully implemented. Moreover,
competition experiments revealed that the 4-exo cyclization is
fundamentally preferred over other modes (5-exo, 6-exo, and 6-endo)
of cyclization.
Q. Zhao, L. Li, Y. Fang, D. Sun, C. Li, J. Org. Chem., 2009,
74, 459-462.
Air-stable palladium complexes with phosphinous acid ligands serve as
efficient catalysts for various cross-coupling reactions of vinyl and aryl
chlorides with arylboronic acids, arylzinc reagents, and thiols.
G. Y. Li, J. Org. Chem., 2002, 67, 3643-3650.
A hydrothiolation of aromatic alkynes with thiophenols by anti-Markonikov
addition in the presence of β-cyclodextrin in water gives E-vinyl
sulfides in excellent yields. β-Cyclodextrin can be recovered and reused for a
number of runs without any loss of activity.
R. Sridhar, K. Surendra, N. S. Krishnaveni, B. Srinivas, K. R. Rao, Synlett, 2006,
3495-3497.
In the presence of CuI and Cs2CO3, a variety of thiols
reacted with arylpropiolic acids to afford the corresponding vinyl sulfides in
good to excellent yields with high stereoselectivity for Z-isomers via a
decarboxylative cross-coupling.
S. Ranjit, Z. Duan, P. Zhang, X. Liu, Org. Lett., 2010,
12, 4134-4136.
The reaction of an alkyne with an alkanethiol in the presence of a catalytic amount of
cesium carbonate and TEMPO as a radical inhibitor in DMSO provides the corresponding 1-alkenyl alkyl sulfide
adduct in good yield with high Z-selectivity.
A. Kondoh, K. Takami, H. Yorimitsu, K. Oshima, J. Org. Chem., 2005, 70, 6468-6473.
Tp*Rh(PPh3)2 (Tp* =
hydrotris(3,5-dimethylpyrazolyl)borate) is a highly active catalyst for
alkyne hydrothiolation with alkyl and aryl thiols. Hydrothiolation using
alkyl thiols proceeds with excellent regioselectivity, providing convenient
access to branched alkyl vinyl sulfides. A mixture of regioisomers is
obtained when using aryl thiols.
C. Cao, L. R. Fraser, J. A. Love, J. Am. Chem. Soc.,
2005, 127, 17614-17615.
Unsymmetrical internal alkynes such as ethyl phenylpropiolate successfully
underwent Pt-catalyzed decarbonylative arylthiolation by thioesters.
F. Yamashita, H. Kuniyasu, J. Terao, N. Kambe, Org. Lett., 2008,
10, 101-104.
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