Iron-Catalyzed Mizoroki–Heck Cross-Coupling Reaction with Styrenes

Authors

  • Rafal Loska,

    1. Laboratory of Glycochemistry and Asymmetric Synthesis (LGSA), Swiss Institute of Technology in Lausanne (EPFL), Batochime, CH 1015 Lausanne, Switzerland, Fax: (+41)-21-693-9375
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    • Both R. Loska and C. M. Rao Volla contributed equally to this project

  • Chandra M. Rao Volla,

    1. Laboratory of Glycochemistry and Asymmetric Synthesis (LGSA), Swiss Institute of Technology in Lausanne (EPFL), Batochime, CH 1015 Lausanne, Switzerland, Fax: (+41)-21-693-9375
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    • Both R. Loska and C. M. Rao Volla contributed equally to this project

  • Pierre Vogel

    1. Laboratory of Glycochemistry and Asymmetric Synthesis (LGSA), Swiss Institute of Technology in Lausanne (EPFL), Batochime, CH 1015 Lausanne, Switzerland, Fax: (+41)-21-693-9375
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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[BOND]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.

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