Thiocyanation of Indole. Some Reactions of 3-Thiocyanoindole

Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives

“…The thiocyanato group is known to undergo nucleophilic attack both at the sulfur atom (by softer nucleophiles) and at the carbon atom (by harder nucleophiles), which both result in the formation of sulfur-containing products. 1,2 Therefore, the direct thiocyanation of aromatic compounds is a very important reaction in organic synthesis, and several reports on the thiocyanation of organic compounds can be found in the literature 3 .…”

Simple and Highly Efficient Catalytic Thiocyanation of Aromatic Compounds in Aqueous Media

“…On the other hand, the nucleophilic attack of thiocyanate ion at an aromatic nucleus via displacement reactions is not an easy way to form thiocyanated compounds [2 -5]. So, several methods have been developed for the electrophilic thiocyanation of arenes [6] [7] such as bromine/potassium thiocyanate [8], N-thiocyanatosuccinimide [9], an thiocyanate salt in the presence of ceric ammonium nitrate (CAN) [10], acidic montmorillonite K10 clay [11], I 2 /MeOH [2], Oxone [12], pentavalent iodine, i.e., 2-iodoxybenzoic acid (IBX) [13], or potassium peroxydisulfate/copper(II) sulfate [14]. However, these methodologies suffer from one or more drawbacks such as the use of toxic transition metals as oxidants [1], the toxicity of reagents in general [7] [8], large excess of catalyst [11], and performances under certain special conditions.…”

Regioselective Thiocyanation of Aromatic and Heteroaromatic Compounds Using [2-(Sulfooxy)ethyl]sulfamic Acid as an Efficient, Recyclable Organocatalyst and Novel Difunctional Brønsted Acid

“…On the other hand, thiocyanosubstituted compounds are a useful precursor for the synthesis of organosulfur compounds, in which the thiocyanate group will be readily transferred to other functional groups such as sulfide [13], aryl nitrile [17], thiocarbamate [18,19], and thionitrile [20]. Several methods have been developed for the thiocyanation of arenes by using various reagents [21][22][23] such as N-thiocyanatosuccinimide [24], ceric ammonium nitrate (CAN) [25], acidic montmorillonite K10 clay [26], iodine/methanol [27], diethyl azodicarboxylate [28], IL-OPPh 2 [29], pentavalent iodine [30], IBX [31], FeCl 3 [32], potassium peroxydisulfate-copper(II) [33], and Selectfluor [34]. However, most of the reported methods for the synthesis of aryl thiocyanates are associated with one or more of the following drawbacks such as use of strongly acidic or oxidizing conditions, high temperatures, low yields, long reaction times, the use of large amounts of catalyst, and the use of toxic or expensive catalysts.…”