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Synthesis of vinyl sulfides
Recent Literature
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.
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.
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.
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.
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