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Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids.

ABSTRACT: A 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.

SUBMITTER: Neumann H

PROVIDER: S-EPMC7435766 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Efficient Palladium-Catalyzed Synthesis of 2-Aryl Propionic Acids.

Neumann Helfried H Sergeev Alexey G AG Spannenberg Anke A Beller Matthias M

Molecules (Basel, Switzerland) 20200728 15

A 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) (<b>9</b>) 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 h ...[more]

PMID: 32731527

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