Direct Substitution of a Hydroxyl Group by a Carboxyl Group at the Benzylic Position in Benzyl Alcohols by Electrochemical Reduction in the Presence of Carbon Dioxide: Improvement Enabling Electrochemical Direct Carboxylation of Benzyl Alcohols even in the Absence of an Electron-withdrawing Group on the Phenyl Ring
Electrochemical carboxylation of benzyl alcohols even in the absence of an electron-withdrawing group on the phenyl ring was successfully carried out by improving our previous electrolysis conditions. Constant current electrolysis of benzyl alcohols including diphenylmethanol in DMSO containing 0.1...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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The Electrochemical Society of Japan
2023-11-01
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| Series: | Electrochemistry |
| Subjects: | |
| Online Access: | https://www.jstage.jst.go.jp/article/electrochemistry/91/11/91_23-67082/_html/-char/en |
| _version_ | 1827630250318626816 |
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| author | Mizuki HAYAMA Hisanori SENBOKU |
| author_facet | Mizuki HAYAMA Hisanori SENBOKU |
| author_sort | Mizuki HAYAMA |
| collection | DOAJ |
| description | Electrochemical carboxylation of benzyl alcohols even in the absence of an electron-withdrawing group on the phenyl ring was successfully carried out by improving our previous electrolysis conditions. Constant current electrolysis of benzyl alcohols including diphenylmethanol in DMSO containing 0.1 mol dm−3 Bu4NBF4 in the presence of carbon dioxide using an undivided cell equipped with a platinum plate cathode and a magnesium rod anode at room temperature resulted in direct substitution of a hydroxyl group by a carboxyl group at the benzylic position to give the corresponding arylacetic acids including diphenylacetic acid in moderate to good yields. Although the effect of DMSO as a solvent is still unclear, the results indicate the potential for a useful, convenient, and eco-friendly synthetic method for arylacetic acids from benzyl alcohols. |
| first_indexed | 2024-03-09T14:03:16Z |
| format | Article |
| id | doaj.art-d23609115ab34aabb5f3722c0c3f65e5 |
| institution | Directory Open Access Journal |
| issn | 2186-2451 |
| language | English |
| last_indexed | 2024-03-09T14:03:16Z |
| publishDate | 2023-11-01 |
| publisher | The Electrochemical Society of Japan |
| record_format | Article |
| series | Electrochemistry |
| spelling | doaj.art-d23609115ab34aabb5f3722c0c3f65e52023-11-30T06:15:00ZengThe Electrochemical Society of JapanElectrochemistry2186-24512023-11-01911111201111201110.5796/electrochemistry.23-67082electrochemistryDirect Substitution of a Hydroxyl Group by a Carboxyl Group at the Benzylic Position in Benzyl Alcohols by Electrochemical Reduction in the Presence of Carbon Dioxide: Improvement Enabling Electrochemical Direct Carboxylation of Benzyl Alcohols even in the Absence of an Electron-withdrawing Group on the Phenyl RingMizuki HAYAMA0Hisanori SENBOKU1https://orcid.org/0000-0003-2205-626XGraduate School of Chemical Sciences and Engineering, Hokkaido UniversityGraduate School of Chemical Sciences and Engineering, Hokkaido UniversityElectrochemical carboxylation of benzyl alcohols even in the absence of an electron-withdrawing group on the phenyl ring was successfully carried out by improving our previous electrolysis conditions. Constant current electrolysis of benzyl alcohols including diphenylmethanol in DMSO containing 0.1 mol dm−3 Bu4NBF4 in the presence of carbon dioxide using an undivided cell equipped with a platinum plate cathode and a magnesium rod anode at room temperature resulted in direct substitution of a hydroxyl group by a carboxyl group at the benzylic position to give the corresponding arylacetic acids including diphenylacetic acid in moderate to good yields. Although the effect of DMSO as a solvent is still unclear, the results indicate the potential for a useful, convenient, and eco-friendly synthetic method for arylacetic acids from benzyl alcohols.https://www.jstage.jst.go.jp/article/electrochemistry/91/11/91_23-67082/_html/-char/enelectrochemical fixation of carbon dioxideelectroorganic synthesisbenzyl alcoholarylacetic acid |
| spellingShingle | Mizuki HAYAMA Hisanori SENBOKU Direct Substitution of a Hydroxyl Group by a Carboxyl Group at the Benzylic Position in Benzyl Alcohols by Electrochemical Reduction in the Presence of Carbon Dioxide: Improvement Enabling Electrochemical Direct Carboxylation of Benzyl Alcohols even in the Absence of an Electron-withdrawing Group on the Phenyl Ring Electrochemistry electrochemical fixation of carbon dioxide electroorganic synthesis benzyl alcohol arylacetic acid |
| title | Direct Substitution of a Hydroxyl Group by a Carboxyl Group at the Benzylic Position in Benzyl Alcohols by Electrochemical Reduction in the Presence of Carbon Dioxide: Improvement Enabling Electrochemical Direct Carboxylation of Benzyl Alcohols even in the Absence of an Electron-withdrawing Group on the Phenyl Ring |
| title_full | Direct Substitution of a Hydroxyl Group by a Carboxyl Group at the Benzylic Position in Benzyl Alcohols by Electrochemical Reduction in the Presence of Carbon Dioxide: Improvement Enabling Electrochemical Direct Carboxylation of Benzyl Alcohols even in the Absence of an Electron-withdrawing Group on the Phenyl Ring |
| title_fullStr | Direct Substitution of a Hydroxyl Group by a Carboxyl Group at the Benzylic Position in Benzyl Alcohols by Electrochemical Reduction in the Presence of Carbon Dioxide: Improvement Enabling Electrochemical Direct Carboxylation of Benzyl Alcohols even in the Absence of an Electron-withdrawing Group on the Phenyl Ring |
| title_full_unstemmed | Direct Substitution of a Hydroxyl Group by a Carboxyl Group at the Benzylic Position in Benzyl Alcohols by Electrochemical Reduction in the Presence of Carbon Dioxide: Improvement Enabling Electrochemical Direct Carboxylation of Benzyl Alcohols even in the Absence of an Electron-withdrawing Group on the Phenyl Ring |
| title_short | Direct Substitution of a Hydroxyl Group by a Carboxyl Group at the Benzylic Position in Benzyl Alcohols by Electrochemical Reduction in the Presence of Carbon Dioxide: Improvement Enabling Electrochemical Direct Carboxylation of Benzyl Alcohols even in the Absence of an Electron-withdrawing Group on the Phenyl Ring |
| title_sort | direct substitution of a hydroxyl group by a carboxyl group at the benzylic position in benzyl alcohols by electrochemical reduction in the presence of carbon dioxide improvement enabling electrochemical direct carboxylation of benzyl alcohols even in the absence of an electron withdrawing group on the phenyl ring |
| topic | electrochemical fixation of carbon dioxide electroorganic synthesis benzyl alcohol arylacetic acid |
| url | https://www.jstage.jst.go.jp/article/electrochemistry/91/11/91_23-67082/_html/-char/en |
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