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- ItemEfficient palladium-catalyzed synthesis of 2-aryl propionic acids(Basel : MDPI, 2020) Neumann, Helfried; Sergeev, Alexey G.; Spannenberg, Anke; Beller, MatthiasA flexible two-step, one-pot procedure was developed to synthesize 2-aryl propionic acids including the anti-inflammatory drugs naproxen and flurbiprofen. Optimal results were obtained in the presence of the novel ligand neoisopinocampheyldiphenylphosphine (NISPCPP) (9) which enabled the efficient sequential palladium-catalyzed Heck coupling of aryl bromides with ethylene and hydroxycarbonylation of the resulting styrenes to 2-aryl propionic acids. This cascade transformation leads with high regioselectivity to the desired products in good yields and avoids the need for additional purification steps. © 2020 by the authors. Licensee MDPI, Basel, Switzerland.
- ItemEfficient Synthesis of Novel Plasticizers by Direct Palladium-Catalyzed Di- or Multi-carbonylations(Weinheim : Wiley-VCH, 2022) Hu, Yuya; Sang, Rui; Vroemans, Robby; Mollaert, Guillaume; Razzaq, Rauf; Neumann, Helfried; Junge, Henrik; Franke, Robert; Jackstell, Ralf; Maes, Bert U. W.; Beller, MatthiasDiesters are of fundamental importance in the chemical industry and are used for many applications, e.g. as plasticizers, surfactants, emulsifiers, and lubricants. Herein, we present a straightforward and efficient method for the selective synthesis of diesters via palladium-catalyzed direct carbonylation of di- or polyols with readily available alkenes. Key-to-success is the use of a specific palladium catalyst with the “built-in-base” ligand L16 providing esterification of all alcohols and a high n/iso ratio. The synthesized diesters were evaluated as potential plasticizers in PVC films by measuring the glass transition temperature (Tg) via differential scanning calorimetry (DSC).
- ItemPalladium-Catalyzed Alkoxycarbonylation of sec-Benzylic Ethers(Weinheim : Wiley-VCH Verl., 2020) Schneider, Carolin; Jackstell, Ralf; Maes, Bert U.W.; Beller, MatthiasHerein, we report the palladium-catalyzed synthesis of 3-arylpropionate esters starting from secondary benzylic ethers. With this investigation it could be shown that ethers are suitable starting materials in addition to the established carbonylation reactions of olefins, alcohols, or aryl halides. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.