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Synthesis of thiocyanates

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An electrochemical direct cyanation of readily available thiophenols or thiols with trimethylsilyl cyanide (TMSCN) provides thiocyanates under mild operating conditions. This oxidant- and transition-metal-free cross-coupling method is also suitable for selenols.
C. Jiang, Y. Zhu, H. Li, P. Liu, P. Sun, J. Org. Chem., 2022, 87, 10026-10033.


An interrupted Pummerer reaction of sulfoxides provides thiocyanates under mild conditions via electrophilic activation of the sulfoxide partner and dealkylative functionalization.
U. Todorović, I. Klose, N. Maulide, Org. Lett., 2021, 23, 2510-2513.


Thioethers can be converted to thiocyanates via fluorium-initiated dealkylative cyanation in the presence of selectfluor as the oxidant and trimethylsilyl cyanide as the cyanation reagent. This method is user-friendly, operationally simple, and step-economical.
Y. Chen, H. Qi, N. Chen, D. Ren, J. Xu, Z. Yang, J. Org. Chem., 2019, 84, 9044-9050.


An interrupted Pummerer reaction of sulfoxides provides thiocyanates under mild conditions via electrophilic activation of the sulfoxide partner and dealkylative functionalization.
U. Todorović, I. Klose, N. Maulide, Org. Lett., 2021, 23, 2510-2513.