Synthesis of Vinyl Sulfides using Selenium Ionic Liquid

Samuel R Mendes,Diego Alves,Raquel G Jacob,Gelson Perin,Samuel Thurow,Eder J Lenardão

doi:10.5151/chempro-14bmos-r0143-2

Abstract

Vinyl sulfides are very versatile and useful intermediates in organic synthesis and there are several compounds of natural occurrence bearing the vinyl sulfide group isolated from bloming plants of the tribe Heliantheae (Asteraceae). In addition, vinyl sulfides can be converted into the corresponding aldehyde, ketone or carboxylic acid or ester by acid hydrolysis or through the thio- Claisen rearrangement. On the other hand, ionic liquids (ILs) constitute an interesting alternative to solvents in organic synthesis. Because product isolation or catalyst recycling is very easy in ILs and, in some cases, rate accelerations and/or selectivity improvements are also observed, they are regarded as environmentally friendly green solvents. Due our continuing interest in the synthesis and applications of organochalcogenium chemistry and in new applications for selenium-based ionic liquids, we decide to study the use of [bmim][SeO2(OCH3)] for the synthesis of vinyl sulfides by hydrothiolation of terminal alkynes.

Highlights

Vinyl sulfides are very versatile and useful intermediates in organic synthesis[1] and there are several compounds of natural occurrence bearing the vinyl sulfide group isolated from bloming plants of the tribe Heliantheae (Asteraceae).[2]
A set of experiments were performed to find the best conditions for the synthesis of vinyl sulfides using thiophenol and propargyl alcohol as model compounds (Scheme 1)
42:54:4 a Yields are given for isolated products. b Determined by 1H NMR

Summary

Introduction

Vinyl sulfides are very versatile and useful intermediates in organic synthesis[1] and there are several compounds of natural occurrence bearing the vinyl sulfide group isolated from bloming plants of the tribe Heliantheae (Asteraceae).[2]. A set of experiments were performed to find the best conditions for the synthesis of vinyl sulfides using thiophenol and propargyl alcohol as model compounds (Scheme 1).

Results

Conclusion