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Synthesis of dithiocarbamates


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.

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.

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.

Multicomponent reactions of CS2, sulfoxonium ylides and secondary amines provide β-keto dithiocarbamates, whereas primary amines afforded thiazolidine-2-thiones or thiazole-2-thiones after dehydration in an acidic environment. These simple, versatile, and catalyst-free synthetic methods have a wide substrate scope and excellent functional group tolerance.
N. Kumar, A. Sharma, U. Kumar, S. K. Panday, J. Org. Chem., 2023, 88, 6120-6125.

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.