Synthesis of Unsymmetrical Trisulfides from S-Substituted Sulphenylthiosulphates.

Trisulfide unit is widely found in natural products and has garnered attention due to the unique pharmacological and physiochemical properties. However, despite limited progress, widely applicable approaches for constructing unsymmetrical trisulfides have so far remain scarce. In this work, an easy-to-prepare, solid-state and scalable reagent, S-substituted sulphenylthiosulphate, has been developed for the divergent synthesis of unsymmetrical trisulfides.

Direct methylthiolation of -, -, and -nucleophiles with sodium -methyl thiosulfate.

A practical and efficient methylthiolation that employed the typical Bunte salt sodium -methyl sulfothioate as the sulfur source was described. This reagent could react with a variety of compounds such as alkynes, 1,3-diketones, thiols, selenol and -phosphine oxides, affording methylthiolated products in moderate to excellent yields. The advantages such as easy preparation, air- and moisture-stability and high tolerance of functional groups demonstrated the potential of this reagent to be widely applied in organic synthesis.

Bunte Salt CHFSSONa: An Efficient and Odorless Reagent for Monofluoromethylthiolation.

A practical and efficient monofluoromethylthiolation that employs the typical Bunte salt, sodium S-(fluoromethyl) sulfurothioate, as the sulfur source is described. This reagent reacts readily with a variety of aryl amines and aryl thiols. The high tolerance of functional groups demonstrates the potential of this reaction.