Magnesium-induced copper-catalyzed synthesis of unsymmetrical diaryl chalcogenide compounds from aryl iodide via cleavage of the Se-Se or S-S bond

Nobukazu Taniguchi; Tetsuo Onami

doi:10.1021/jo030300+

Magnesium-induced copper-catalyzed synthesis of unsymmetrical diaryl chalcogenide compounds from aryl iodide via cleavage of the Se-Se or S-S bond

J Org Chem. 2004 Feb 6;69(3):915-20. doi: 10.1021/jo030300+.

Authors

Nobukazu Taniguchi¹, Tetsuo Onami

Affiliation

¹ Department of Chemistry, Fukushima Medical University, Fukushima 960-1295, Japan. taniguti@fmu.ac.jp

PMID: 14750822
DOI: 10.1021/jo030300+

Abstract

The methodology for a copper-catalyzed preparation of diaryl chalcogenide compounds from aryl iodides and diphenyl dichalcogenide molecules is reported. Unsymmetrical diaryl sulfide or diaryl selenide can be synthesized from aryl iodide and PhYYPh (Y = S, Se) with a copper catalyst (CuI or Cu(2)O) and magnesium metal in one pot. This reaction can be carried out under neutral conditions according to an addition of magnesium metal as the reductive reagent. Furthermore, it is efficiently available for two monophenylchalcogenide groups generated from diphenyl dichalcogenide.