4.5 Article

The Mizoroki-Heck Reaction in Tunable Aryl Alkyl Ionic Liquids

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2022, 期 6, 页码 -

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200008

关键词

Homogeneous catalysis; Imidazolium salts; Ionic liquids; Mizoroki-Heck reaction

资金

  1. Bundesministerium fur Bildung und Forschung (MinSEM) [033R141G]
  2. Deutsche Forschungsgemeinschaft [SPP 1708, STR 526/20-1/2]
  3. Projekt DEAL

向作者/读者索取更多资源

This study reports the use of TAAILs as solvents in the Mizoroki-Heck reaction. By optimizing the reaction conditions, efficient synthesis of (E)-stilbene derivatives with high yields was achieved. The catalytic system using TAAILs showed higher yields compared to other commercially available ionic liquids.
We report the use of imidazolium based tunable aryl alkyl ionic liquids (TAAILs) as solvents in the Mizoroki-Heck reaction. Different commercially available palladium sources, inorganic bases, TAAILs and reaction conditions were tested for the synthesis of trans-stilbene using bromobenzene and styrene. A variety of different stilbene derivatives were synthesized with exclusive formation of the (E)-isomers and isolated yields up to 97 %. We were able to optimize the reaction conditions using only 0.25 mol% of Pd(OAc)(2) as the catalyst and a reaction time of 4 hours. No additional ligands or additives are used in the reaction. The catalytic system using TAAILs achieved higher yields than commercially available imidazolium and phosphonium ionic liquids, demonstrating the potential of tailored ionic liquids as a reaction medium for the Mizoroki-Heck reaction.

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