4.5 Article

Formamidines - Versatile Ligands for Zinc-Catalyzed Hydrosilylation and Iron-Catalyzed Epoxidation Reactions

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 25, Pages 4893-4901

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000648

Keywords

Homogeneous catalysis; Zinc; Iron; Amidine ligands; Hydrosilylation; Epoxidation

Funding

  1. Deutsche Forschungsgemeinschaft (DFG)
  2. Graduiertenkolleg [1213]
  3. Max-Buchner-Forschungsstiftung (DECHEMA)

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In the present study the abilities of catalysts modified by formamidine ligands have been examined in the zinc-catalyzed hydrosilylation of ketones and the iron-catalyzed epoxidation of stilbene. In case of hydrosilylation diethylzinc combined with easily accessible formamidine ligands allow for the efficient reduction of various aryl and alkyl ketones. By using a convenient in situ catalyst system high turnover frequencies up to more than 1.000 h(-1) and a broad functional group tolerance were achieved. Moreover, the formamidine ligands were successfully applied in the iron-catalyzed epoxidation of stilbene with hydrogen peroxide in good yield and chemoselectivity.

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