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.
The combination of
potassium sulfide and chloroform provides an efficient and practical thiocarbonyl surrogate. A variety of dithiocarbamates
can be synthesized in one-pot reactions
in which the thiocarbonyl motif was generated in situ.
W. Tan, N. Jänsch, T. Öhlmann, F.-J. Meyer-Almes, X. Jiang,
Org. Lett., 2019, 21, 7484-7488.
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.
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.