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Iron‐Catalyzed Mizoroki–Heck Cross‐Coupling Reaction with Styrenes
Author(s) -
Loska Rafal,
Volla Chandra M. Rao,
Vogel Pierre
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800662
Subject(s) - chemistry , aryl , catalysis , ligand (biochemistry) , medicinal chemistry , picolinic acid , heck reaction , sulfoxide , stereoselectivity , coupling reaction , organic chemistry , polymer chemistry , palladium , alkyl , biochemistry , receptor
In the presence of iron(II) chloride (FeCl 2 ; 20 mol%) and potassium tert ‐butoxide ( t‐ BuOK; 4 equiv.) in dimethyl sulfoxide (DMSO), aryl and heteroaryl iodides undergo stereoselective Mizoroki–Heck CC 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.