Synthesis of Nitriles <i>via</i> the Iodine-Mediated Dehydrosulfurization of Thioamides

Abstract

A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I 2) is described herein. The reaction of thioamides with I 2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.

Rapid assembly of structurally diverse cyanamides and disulfanes via base-mediated aminoalkylation of aryl thiourea

“…I( iii ) reagents or iodine-mediated desulfurization of thioamide or dithiocarbamate are the most useful methods to obtain N-substituted cyanamides. 9 Further, transition metal-catalyzed desulphurization is also an efficient method for the synthesis of cyanamides. 10 It is a pity that sulfphur was abandoned in this progress.…”