Title

Synthesis of Unsymmetrical Trisulfides from S‐Substituted Sulphenylthiosulphates.

Authors

Liang, Shuaishuai; Ma, Liye; Guo, Zihao; Liu, Fanmin; Lin, Zijian; Yi, Wenbin

Abstract

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. Alkyl electrophile substrates, including bromides, chlorides, iodides and tosylates, with diverse substituents are smoothly converted to the corresponding trisulfides with S‐substituted sulphenylthiosulphates and thiourea as another sulfur source. Furthermore, the late‐stage modification of drug molecules was successfully achieved through this method.

Subjects

NATURAL products; IODIDES; BROMIDES; CHLORIDES; SULFUR

Publication

Angewandte Chemie, 2024, Vol 136, Issue 28, p1

ISSN

0044-8249

Publication type

Academic Journal

DOI

10.1002/ange.202404139