Rhodium(CAAC)-Catalyzed Arene Hydrogenation of Benzo-Fused N-Heterocycles to Saturated Building Blocks with an all-cis Configuration

Christian H. Schiwek, Simone Stegbauer, Thomas Pickl, Thorsten Bach

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Saturated carbo- and heterocyclic building blocks can be readily obtained by the hydrogenation of aromatic carbo- and heterocycles. Although a variety of methods have been established to accomplish this transformation for simple arenes, the hydrogenation of aromatic N-heterocycles is less explored. We herein report a diastereoselective arene hydrogenation which was applied to an array of benzo-fused N-heterocycles. A total of 48 saturated heterocycles was obtained by hydrogenation in the presence of the rhodium complex Cy(CAAC)Rh(cod)Cl in yields of 72–98% with moderate to high diastereoselectivities exhibiting the hydrogen atoms in an all-cis arrangement. The high tolerance towards functional groups enables the formation of valuable saturated products, which offer a starting point for further derivatization. (Figure presented.).

Original languageEnglish
Pages (from-to)3360-3365
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume364
Issue number19
DOIs
StatePublished - 4 Oct 2022

Keywords

  • Heterocycles
  • Heterogeneous catalysis
  • High-pressure chemistry
  • Hydrocarbons
  • Hydrogenation

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