Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols

Abstract

In this paper we report an efficient and mild procedure for the conversion of organic thiocyanates to thiols in the presence of phosphorus pentasulfide (P2S5) in refluxing toluene. The method avoids the use of expensive and hazardous transition metals and harsh reducing agents, as required by reported methods, and provides an attractive alternative to the existing methods for the conversion of organic thiocyanates to thiols.

Electrooxidation Is a Promising Approach to Functionalization of Pyrazole-Type Compounds

“…Thiocyanation of the C–H bond of arenes is an effective tool for C–S coupling [ 81 , 82 , 83 , 84 ]. The resulting aryl thiocyanates are valuable precursors of sulfur and nitrogen-containing compounds (thiols [ 85 ], (di)sulfides [ 86 , 87 ], dithiocarbamates [ 88 ], thiazoles [ 89 ], tetrazoles [ 90 ]), and are highly bioactive compounds (antifungal [ 91 ], antitumor [ 92 ], antiparasitic [ 93 ]). Recently synthesized thiocyanates of pyrazole derivatives also have sufficient antifungal [ 94 ] and antitumor [ 95 ] activity.…”

Metal-free hydrophosphorodithiolation of alkynes with P4S10 and alcohols leading to vinyl phosphorodithioates

“…11 On the other hand, as a simple and commercially available thionation reagent, P 4 S 10 has attracted great interest from chemists for the construction of sulfur-containing compounds in synthetic chemistry. 12 Very recently, Zhou and Lu described an elegant method for the synthesis of allyl dialkylphosphorodithioates through ring-opening of spirovinylcyclopropyl oxindoles with P 4 S 10 and alcohols. 13 With our continued interest in the development of new reactions to access sulfur-containing compounds, 14 herein, we wish to present a simple and efficient multi-component reaction strategy for the construction of vinyl phosphorodithioates via metal-free hydrophosphorodithiolation of alkynes with P 4 S 10 and alcohols (Scheme 1e).…”

Thiocyanation of Allylic Alcohols Promoted by Trifluoroacetic Acid

“…[7] And Moore found an indole alkaloid containing thiocyanate group from the blue-green algae hapalosiphon welwitschia (welwitindolinone). [11] These compounds holding CÀ SCN bond are used as versatile synthetic precursors for accessing organosulfur compounds and other products, [12][13][14] such as thiols, [15] thioethers, [16,17] thioesters, [18] hetero-cycles, [19] and bi-/tri-fluoromethyl sulfides. [20,21] As significant one of them, allylic thiocyanates have gained the most widespread popularity among chemists.…”