Electrochemical β‐Selective Hydrocarboxylation of Styrene Using CO2 and Water
Abstract The carboxylation of hydrocarbons using CO2 as a one‐carbon building block is an attractive route for the synthesis of carboxylic acids and their derivatives. Until now, chemical carboxylation catalyzed by organometallic nucleophiles and reductants has been generally adopted particularly fo...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2020-02-01
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| Series: | Advanced Science |
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| Online Access: | https://doi.org/10.1002/advs.201900137 |
| _version_ | 1819068873353199616 |
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| author | Younghye Kim Gyeong Do Park Mani Balamurugan Jiwon Seo Byoung Koun Min Ki Tae Nam |
| author_facet | Younghye Kim Gyeong Do Park Mani Balamurugan Jiwon Seo Byoung Koun Min Ki Tae Nam |
| author_sort | Younghye Kim |
| collection | DOAJ |
| description | Abstract The carboxylation of hydrocarbons using CO2 as a one‐carbon building block is an attractive route for the synthesis of carboxylic acids and their derivatives. Until now, chemical carboxylation catalyzed by organometallic nucleophiles and reductants has been generally adopted particularly for the precise selectivity control of carboxylation sites. As another approach, electrochemical carboxylation has been attempted but these carboxylation reactions are limited to only a few pathways. In the case of styrene, dicarboxylation at the α‐ and β‐positions is mostly observed with electrochemical carboxylation while site‐selective hydrocarboxylations are hardly achieved. In this study, electrochemical β‐selective hydrocarboxylation of styrene using CO2 and water is developed, in which the site selectivity can be precisely controlled between β‐hydrocarboxylation and dicarboxylation without the aid of homogeneous catalysts. In this platform, water is used as proton source in the β‐hydrocarboxylation of styrene where its addition results in significant enhancement of the selectivity toward β‐hydrocarboxylation. This work provides insights into new strategies for site‐selectivity‐controllable carboxylation with CO2 using an electrochemical platform. |
| first_indexed | 2024-12-21T16:41:04Z |
| format | Article |
| id | doaj.art-41faec3983ae40e88963059debcaca82 |
| institution | Directory Open Access Journal |
| issn | 2198-3844 |
| language | English |
| last_indexed | 2024-12-21T16:41:04Z |
| publishDate | 2020-02-01 |
| publisher | Wiley |
| record_format | Article |
| series | Advanced Science |
| spelling | doaj.art-41faec3983ae40e88963059debcaca822022-12-21T18:57:06ZengWileyAdvanced Science2198-38442020-02-0173n/an/a10.1002/advs.201900137Electrochemical β‐Selective Hydrocarboxylation of Styrene Using CO2 and WaterYounghye Kim0Gyeong Do Park1Mani Balamurugan2Jiwon Seo3Byoung Koun Min4Ki Tae Nam5Department of Materials Science and Engineering Seoul National University Seoul 151‐744 Republic of KoreaDepartment of Materials Science and Engineering Seoul National University Seoul 151‐744 Republic of KoreaDepartment of Materials Science and Engineering Seoul National University Seoul 151‐744 Republic of KoreaDepartment of Chemistry School of Physics and Chemistry Gwangju Institute of Science and Technology Gwangju 61005 Republic of KoreaClean Energy Research Center Korea Institute of Science and Technology 5 Hwarang‐ro 14‐gil, Seongbuk‐gu Seoul 02792 Republic of KoreaDepartment of Materials Science and Engineering Seoul National University Seoul 151‐744 Republic of KoreaAbstract The carboxylation of hydrocarbons using CO2 as a one‐carbon building block is an attractive route for the synthesis of carboxylic acids and their derivatives. Until now, chemical carboxylation catalyzed by organometallic nucleophiles and reductants has been generally adopted particularly for the precise selectivity control of carboxylation sites. As another approach, electrochemical carboxylation has been attempted but these carboxylation reactions are limited to only a few pathways. In the case of styrene, dicarboxylation at the α‐ and β‐positions is mostly observed with electrochemical carboxylation while site‐selective hydrocarboxylations are hardly achieved. In this study, electrochemical β‐selective hydrocarboxylation of styrene using CO2 and water is developed, in which the site selectivity can be precisely controlled between β‐hydrocarboxylation and dicarboxylation without the aid of homogeneous catalysts. In this platform, water is used as proton source in the β‐hydrocarboxylation of styrene where its addition results in significant enhancement of the selectivity toward β‐hydrocarboxylation. This work provides insights into new strategies for site‐selectivity‐controllable carboxylation with CO2 using an electrochemical platform.https://doi.org/10.1002/advs.201900137carbon fixationcarboxylationCO2 reductionelectrochemistry |
| spellingShingle | Younghye Kim Gyeong Do Park Mani Balamurugan Jiwon Seo Byoung Koun Min Ki Tae Nam Electrochemical β‐Selective Hydrocarboxylation of Styrene Using CO2 and Water Advanced Science carbon fixation carboxylation CO2 reduction electrochemistry |
| title | Electrochemical β‐Selective Hydrocarboxylation of Styrene Using CO2 and Water |
| title_full | Electrochemical β‐Selective Hydrocarboxylation of Styrene Using CO2 and Water |
| title_fullStr | Electrochemical β‐Selective Hydrocarboxylation of Styrene Using CO2 and Water |
| title_full_unstemmed | Electrochemical β‐Selective Hydrocarboxylation of Styrene Using CO2 and Water |
| title_short | Electrochemical β‐Selective Hydrocarboxylation of Styrene Using CO2 and Water |
| title_sort | electrochemical β selective hydrocarboxylation of styrene using co2 and water |
| topic | carbon fixation carboxylation CO2 reduction electrochemistry |
| url | https://doi.org/10.1002/advs.201900137 |
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