Issue 28, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
21 Feb 2017
Accepted
14 Mar 2017
First published
14 Mar 2017

Chem. Commun., 2017,53, 3982-3985

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, 53, 3982 DOI: 10.1039/C7CC01377A

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