A novel and efficient synthesis of selenides

He M Lin,Jun Yang,Kun D Liu,Zhi H Li,Yu Tang,Yuan M Zhang

doi:10.3998/ark.5550190.0013.814

Abstract

Under nitrogen atmosphere, a simple and efficient procedure for the synthesis of symmetrical selenides has been developed by the reaction of aryl or alkyl halides with magnesium (1.5 equiv) and elemental selenium (1.0 equiv) in the absence of catalyst and ligand in THF and toluene under reflux at 86°C. This protocol has been utilized for the synthesis of a variety of symmetrical selenides in good to excellent yields.

Highlights

Organoselenium chemistry has been the subject of constant scientific interest over the past 30 years, and now is a very useful tool in the hands of synthetic chemists.[1]
An effective method to synthesize unsymmetrical selenides has been reported through the reaction of organic halides with the product of diselenide reduction.[8]
We report the efficient synthesis of symmetrical selenides by a novel method

Summary

Introduction

Organoselenium chemistry has been the subject of constant scientific interest over the past 30 years, and now is a very useful tool in the hands of synthetic chemists.[1]. We find that aryl and alkyl bromides react with magnesium and elemental selenium in THF-toluene in the absence of catalyst and ligand to afford corresponding symmetrical selenides in high yield. Diphenyl selenide was afforded in 12% yield (Table 1, entry 1) by employing equivalent amount of magnesium to selenium.

Results

Conclusion