Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO

An efficient one-step synthesis of diarylacetic acids was successfully performed by electrochemical direct carboxylation of diarylmethanol compounds in DMSO. Constant-current electrolysis of diarylmethanol species in DMSO using a one-compartment cell equipped with a Pt cathode and a Mg anode in the presence of carbon dioxide induced reductive C(sp<sup>3</sup>)-O bond cleavage at the benzylic position in diarylmethanol compounds and subsequent fixation of carbon dioxide to produce diarylacetic acids in good yield. This protocol provides a novel and simple approach to diarylacetic acids from diarylmethanol species and carbon dioxide without transformation of the hydroxy group into appropriate leaving groups, such as halides and esters including carbonates.

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Publication Details

Journal
Beilstein Journal of Organic Chemistry
Published
2024-09-20
DOI
https://doi.org/10.3762/bjoc.20.203
Citations
4
Primary Topic
Carbon dioxide utilization in catalysis
Type
article
Field-Weighted Citation Impact
0.71

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article

Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO

Hisanori Senboku, Mizuki Hayama
4 citations
Beilstein Journal of Organic Chemistry
Carbon dioxide utilization in catalysis
0.71
article

Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO

Hisanori Senboku, Mizuki Hayama
article en
4 citations

Abstract

An efficient one-step synthesis of diarylacetic acids was successfully performed by electrochemical direct carboxylation of diarylmethanol compounds in DMSO. Constant-current electrolysis of diarylmethanol species in DMSO using a one-compartment cell equipped with a Pt cathode and a Mg anode in the presence of carbon dioxide induced reductive C(sp<sup>3</sup>)-O bond cleavage at the benzylic position in diarylmethanol compounds and subsequent fixation of carbon dioxide to produce diarylacetic acids in good yield. This protocol provides a novel and simple approach to diarylacetic acids from diarylmethanol species and carbon dioxide without transformation of the hydroxy group into appropriate leaving groups, such as halides and esters including carbonates.

Beilstein Journal of Organic ChemistryVol. 20
Hokkaido University (JP)
Hokkaido University, Japan Society for the Promotion of Science
Clean water and sanitation
Openalex Percentile: Top 39%
Carbon dioxide utilization in catalysis
0.71
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