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Metallic reductant-free synthesis of α-substituted propionic acid derivatives through hydrocarboxylation of alkenes with a formate salt

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Abstract

A PGeP–pincer palladium-catalyzed hydrocarboxylation of styrenes to obtain pharmaceutically important α-arylpropionic acid derivatives was achieved using a formate salt as both a reductant and a CO2 source. The reaction was also applicable to vinylsulfone and acrylates. Isotope labeling experiments demonstrated that a CO2-recycling mechanism is operative through generation and reaction of a benzylpalladium complex as a carbon nucleophile. This protocol has realized a mild and atom economical CO2-fixation reaction without the necessity of using strong metallic reductants.

Graphical abstract: Metallic reductant-free synthesis of α-substituted propionic acid derivatives through hydrocarboxylation of alkenes with a formate salt

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Publication details

The article was received on 21 Feb 2017, accepted on 14 Mar 2017, published on 14 Mar 2017 and first published online on 14 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC01377A
Citation: Chem. Commun., 2017, Advance Article
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    Metallic reductant-free synthesis of α-substituted propionic acid derivatives through hydrocarboxylation of alkenes with a formate salt

    J. Takaya, K. Miyama, C. Zhu and N. Iwasawa, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC01377A

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