Iron-catalyzed mizoroki-heck cross-coupling reaction with styrenes

Abstract

In the presence of iron(II) chloride (FeCl2; 20 mol%) and potassium tert-butoxide (t-BuOK; 4 equiv.) in dimethyl sulfoxide (DMSO), aryl and heteroaryl iodides undergo stereoselective Mizoroki-Heck C-C cross-coupling reactions with styrenes at 60°C giving the corresponding (E)-alkenes. The best yields are obtained upon adding a ligand (80 mol%) such as proline or picolinic acid. Aryl bromides and pyridinyl bromides are also coupled with styrenes but in lower yields. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.