Categories: C-S Bond Formation >
Synthesis of dithiocarbamates
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Recent Literature
A highly efficient, mild and simple synthesis of dithiocarbamates is based on
the one-pot reaction of amines, CS2, and alkyl halides without using
a catalyst under solvent-free conditions. The reaction is a highly atom-economic
process for production of S-alkyl thiocarbamates.
N. Azizi, F. Aryanasab, M. R. Saidi, Org. Lett., 2006, 8, 5275-5277.
An efficient copper-mediated three-component coupling reaction of boronic acids,
amines, and carbon disulfide provides a wide range of functionalized
dithiocarbamates in very good yields. The method offers mild reaction conditions,
easily available substrates, wide substrate scope, and high functional-group
tolerance.
C. Qi, T. Guo, W. Xiong,
Synlett, 2016, 27, 2626-2630.
An efficient transition-metal-free one-pot three-component reaction between
diaryliodonium triflates, cyclic and acyclic aliphatic amines, and carbon
disulfide provides biologically relevant S-aryl dithiocarbamates in good
yields under mild conditions. This methodology is robust, scalable,
and exhibits a broad substrate scope.
S. K. Parida, S. Jaiswal, P. Singh, S. Murarka, Org. Lett., 2021, 23, 6401-6406.
An efficient copper-catalyzed C(sp2)-S formation between aryl iodides
and tetramethylthiuram monosulfide (TMTM) provides aryl dithiocarbamates in good
to excellent yields. The high yields, decent functional group compatibility, and
cost-effective substrates make this convenient protocol attractive for C-S bond
formation.
Y.-X. Wu, K. Peng, J.-H. Li, Z.-B. Dong, Synthesis, 2020, 52,
3001-3006.
With only 1 mol% of CuCl2 as catalyst, zinc powder as reductant, and
K2CO3 as base, a highly efficient C-S cross-coupling
reaction of aryl iodides with tetraalkylthiuram disulfides provides
dithiocarbamates in very good yields. This protocol has a broad substrate scope
and uses cheap and readily available starting materials.
Q. Cao, H.-Y. Peng, Y. Cheng, Z.-B. Dong, Synthesis, 2018, 50,
1527-1534.
A copper-catalyzed preparation of aryl dithiocarbamates from aryl iodides and
inexpensive, environmentally benign tetraalkylthiuram disulfides offers mild
reaction conditions, high yields, and broad substrate scope. This approach is
synthetically attractive for the preparation of potentially biologically active
compounds.
Z.-B. Dong, X. Liu, C. Bolm, Org. Lett.,
2017, 19, 5916-5919.
A green and efficient multicomponent reaction provides S-aryl
dithiocarbamates without adding any transition-metal catalysts, ligands, or
photocatalysts under visible light. This method provides a straightforward way
to create valuable S-aryl dithiocarbamates while minimizing chemical
wastes and metal residues in the end products.
G. Li, Q. Yan, Z. Gan, Q. Li, X. Dou, D. Yang,
Org. Lett., 2019, 21, 7851-7856.
An efficient, ligand-free copper-catalyzed coupling of aryl iodides with
tetraalkylthiuram disulfides in water provides a series of S-aryl
dithiocarbamates in good yields.
X.-m. Wu, G.-b. Yan, Synlett, 2019,
30,
610-614.
A three-component coupling involving arynes, CS2, and aliphatic
amines enables a facile synthesis of biologically important S-aryl
dithiocarbamates. This transition-metal-free and mild reaction is scalable and
operates with good functional group compatibility. With 3-triflyloxybenzyne, a
unique four-component coupling incorporating tetrahydrofuran was observed.
S. Bhattarcharjee, S. Deswal, N. Manoj, G. Jindal, A. T. Biju, Org. Lett., 2021, 23,
9083-9088.
The reaction of diazonium tetrafluoroborates and diaryl dichalcogenides
including sulfides, selenides and tellurides on the surface of alumina under
ball-milling enables a convenient, efficient, and general synthesis of a wide
range of diaryl chalcogenides in high purity without any solvent or metal.
N. Mukherjee, T. Chatterjee, B. C. Ranu, J. Org. Chem., 2013,
78, 11110-11114.
A mild, convenient, and practical one-pot procedure gives dithiocarbamates in
good to excellent yields by condensation of amines, CS2, and a
Michael acceptor, under solvent-free conditions at room temperature.
N. Azizi, F. Ebrahimi, E. Aakbari, F. Aryanasab, M. R. Saidi, Synlett, 2007,
2797-2800.
A facile photocatalyzed strategy for difunctionalization of styrenes in the
presence of CS2 and amines provides β-keto dithiocarbamates. However,
4-nitrostyrene and 2-vinylpyridine can only be converted to
2-arylethylthiocarbamates.
R. K. Vishwakarma, S. Kumar, K. N. Singh, Org. Lett., 2021, 23,
4147-4151.