Organic thiocyanates have attracted considerable attention owing to their diverse biological activities and applications as powerful and versatile building blocks in a variety of synthetic transformations. Hence, the development of efficient and practical strategies for their preparation that benefit from simple, inexpensive, and easily accessible starting materials is of prime importance in organic synthesis. In this regards, the direct cyanation of S-H bonds in thiol derivatives has emerged as a powerful and straightforward method for the formation of thiocyanate functionality which avoids tedious multi-step synthesis and pre-functionalization of starting materials that often required in conventional approaches. The present review is an attempt to highlight the most important contributions toward the synthesis of organic thiocyanate via direct S-cyanation of corresponding THIOLS from 1976 to 2022.

An environmentally benign and efficient process for the preparation of thioethers was developed by simple and practical reactions of alkyl halides and THIOLS in water in the presence of K2CO3 or Et3N in very high yields. The reaction of aryl, alkyl, aliphatic and hindered THIOLS with various alkyl halides gave the corresponding products with significant advantages such as high conversions, short reaction time, mild reaction conditions, and low cost, simple workup with good to quantitative yields.

Dithiocarbamic acids and THIOLS are employed in the Bargellini reaction to generate useful intermediates for the synthesis of organic molecules. This is the first time that dithiocarbamic acids are used as nucleophile in this reaction.

BioTHIOLS are the main part of different proteins and matabolites which have tremendous impact on the neutralization of oxidative stress in the cell and stability of the intracellular environment. Metabolite perturbation of these compounds can be indicative of many serious diseases such as weight loss, liver damage, cardiovascular diseases and Alzheimer’s. Thus, tremendous researches have been devoted on the detection of THIOLS via biossensors and nanosensors using electrochemical methods. Higher sensitivity, selectivity, catalytic activity, conductivity, and biocompatibility are the advantage of nanomaterial-based electrochemical sensors. With recent advances in nanotechnology, creating new electrode materials with novel chemical and physical properties has become more accessible using nanoparticles (NPs). The progress of NP-based electrochemical sensors and its applications for bioTHIOLS detection was reviewed in this article. The aim of this effort is to provide the reader a view of the main functions of NPs in conventional and miniaturized electrochemical sensors. As well as, the novel and significant development of biorecognition elements used in conjunction with nanosensors were reported, which motivate more interests in targeted detection of THIOLS in further studies. The references selected based on the following characteristics: appropriate signal amplification, minimum detection limit, and simultaneous-detection capabilities toward thios detection.

In this review, recent advances in transition-metal-catalyzed dehydrative thioetherification of alcohols with THIOLS are discussed. Mechanistic insights for the future development of novel and more efficient catalytic systems are given. The literature has been surveyed up until the end of July 2024.

Reaction of 2-bromo-1, 4-naphthaquinone with THIOLS in chloroform or dichloromethane caused substitution of thioalkyl (aryl) on potions 3 and producing 2-bromo-3-thioalkyl (aryl) -1, 4-dihydroxynaphthalene, which under oxidation gave the corresponding 1, 4-naphthaquinone. While the reaction in presence of sodium acetate in ethanol gave 2-thioalkyl (aryl) - 1, 4-naphthaquinones by substitution with bromine. Reaction of bromonaphthaquinone with hydroxylamine hydrochloride gave 2-amino-3-bromo-1, 4-naphthaquinone. The reaction of bromonaphthaquinone with isoxazole-5 (2H)-ones under reflux condions in ethanol produced 2-ethenylamino-3-bromonaphthaquinone derivatives.