Decarboxylation and Tandem Reduction/Decarboxylation Pathways to Substituted Phenols from Aromatic Carboxylic Acids Using Bimetallic Nanoparticles on Supported Ionic Liquid Phases as Multifunctional Catalysts

Journal of the American Chemical Society, vol. 145, pp. 22845–22854

Abstract

High Resolution Image Download MS PowerPoint Slide Valuable substituted phenols are accessible via the selective decarboxylation of hydroxybenzoic acid derivatives using multifunctional catalysts composed of bimetallic iron–ruthenium nanoparticles immobilized on an amine-functionalized supported ionic liquid phase (Fe 25 Ru 75 @SILP+IL-NEt 2 ). The individual components of the catalytic system are assembled using a molecular approach to bring metal and amine sites into close contact on the support material, providing high stability and high decarboxylation activity. Operating under a hydrogen atmosphere was found to be essential to achieve high selectivity and yields. As the catalyst materials enable also the selective hydrogenation and hydrodeoxygenation of various additional functional groups (i.e., formyl, acyl, and nitro substituents), direct access to the corresponding phenols can be achieved via integrated tandem reactions. The approach opens versatile synthetic pathways for the production of valuable phenols from a wide range of readily available substrates, including compounds derived from lignocellulosic biomass.

Authors 6

1. Natalia Levin

   Max Planck Institute for Chemical Energy Conversion

   Affiliation as printed

   Max Planck Institute for Chemical Energy Conversion, Stiftstr. 34-36, 45470 Mülheim an der Ruhr, Germany

2. Lisa Goclik Aachen Institut für Technische und Makromolekulare Chemie

   RWTH Aachen University · Max Planck Institute for Chemical Energy Conversion

   Affiliation as printed

   Institut für Technische und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 2, 52074 Aachen, Germany

   Max Planck Institute for Chemical Energy Conversion, Stiftstr. 34-36, 45470 Mülheim an der Ruhr, Germany

3. Henrik Walschus

   Max Planck Institute for Chemical Energy Conversion

   Affiliation as printed

   Max Planck Institute for Chemical Energy Conversion, Stiftstr. 34-36, 45470 Mülheim an der Ruhr, Germany

4. Neha Antil

   Max Planck Institute for Chemical Energy Conversion

   Affiliation as printed

   Max Planck Institute for Chemical Energy Conversion, Stiftstr. 34-36, 45470 Mülheim an der Ruhr, Germany

5. Alexis Bordet corresponding

   Max Planck Institute for Chemical Energy Conversion

   Affiliation as printed

   Max Planck Institute for Chemical Energy Conversion, Stiftstr. 34-36, 45470 Mülheim an der Ruhr, Germany

6. Walter Leitner corresponding Aachen Institut für Technische und Makromolekulare Chemie

   RWTH Aachen University · Max Planck Institute for Chemical Energy Conversion

   Affiliation as printed

   Institut für Technische und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 2, 52074 Aachen, Germany

   Max Planck Institute for Chemical Energy Conversion, Stiftstr. 34-36, 45470 Mülheim an der Ruhr, Germany