Categories: C-S Bond Formation >
Synthesis of dithiocarbamates
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.