Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

Claudio C Silveira,Lucas Wolf,Samuel R Mendes

doi:10.1590/s0103-50532010001100016

Abstract

A general new method for the cross-coupling reaction between vinylic selenides and tellurides and Grignard reagents catalyzed by Fe(acac)3 at room temperature is described. This reaction proceeded with retention of configuration, providing the respective alkenes in good to excellent yields. This method is also efficient for the coupling reaction of divinyl chalcogenides with Grignard reagents.

Highlights

Organochalcogenium compounds became the key component of a variety of versatile and useful reagents for organic synthesis
Among the many applications of vinylic selenides, divinylic selenides and vinylic sulfides, the cross-coupling reaction with Grignard reagents catalyzed by Ni18,24-27 and
Transition-metal-catalyzed C-C bond coupling reactions are very important in many areas of science.[43,44]

Summary

Introduction

Organochalcogenium compounds became the key component of a variety of versatile and useful reagents for organic synthesis. We describe our results on the reaction of vinylic selenides and tellurides with Grignard reagents under the catalysis of iron species. The best yield was obtained when a mixture of THF/NMP (3:1) was used as solvent, and the product 3e was obtained in 82% yield, after stirring for h at room temperature (Table 1, entry 4).

Results

Conclusion