Categories: C-N Bond Formation >
Synthesis of thiocarbamoyl halides
In the presence of trifluoromethanesulfonyl chloride, triphenylphosphine, and sodium iodide, a broad range of thiocarbamyl fluorides and isothiocyanates can be synthesized from secondary and primary amines in good yields, respectively. The reactions offer good functional group compatibility.
J. Wei, S. Liang, L. Jiang, W. Yi, J. Org. Chem., 2020, 85, 12374-12381.
Reactions of thiocarbonyl fluoride derived from CF3SiMe3, elemental sulfur, and KF with secondary amines provides a wide variety of thiocarbamoyl fluorides in good yields at room temperature in THF, whereas the reaction with primary amines gives isothiocyanates. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF3 can be used as an alternative.
L. Zhen, H. Fan, X. Wang, L. Jiang, Org. Lett., 2019, 21, 2106-2110.