Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide
We report a direct and efficient electrochemical carboxylation of benzylic C-N bonds with CO₂ at room temperature. The reaction has been successfully applied to both primary and secondary benzylic C-N bonds with the compatibility of a variety of functional groups. This procedure does not require sto...
| Main Authors: | , , , , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
American Chemical Society (ACS)
2020
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| Online Access: | https://hdl.handle.net/1721.1/125787 |
| _version_ | 1826201222103695360 |
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| author | Yang, Dengtao Zhu, Minghui Schiffer, Zachary J. Williams, Kindle Song, Xiaojie Liu, Xiaohui Manthiram, Karthish |
| author2 | Massachusetts Institute of Technology. Department of Chemical Engineering |
| author_facet | Massachusetts Institute of Technology. Department of Chemical Engineering Yang, Dengtao Zhu, Minghui Schiffer, Zachary J. Williams, Kindle Song, Xiaojie Liu, Xiaohui Manthiram, Karthish |
| author_sort | Yang, Dengtao |
| collection | MIT |
| description | We report a direct and efficient electrochemical carboxylation of benzylic C-N bonds with CO₂ at room temperature. The reaction has been successfully applied to both primary and secondary benzylic C-N bonds with the compatibility of a variety of functional groups. This procedure does not require stoichiometric metals, external reducing agents, or sacrificial anodes, making column chromatography unnecessary for product purification. Differential electrochemical mass spectrometry (DEMS) was used to elucidate key intermediates of the electrocarboxylation reaction. |
| first_indexed | 2024-09-23T11:48:07Z |
| format | Article |
| id | mit-1721.1/125787 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T11:48:07Z |
| publishDate | 2020 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1257872022-09-27T22:01:55Z Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide Yang, Dengtao Zhu, Minghui Schiffer, Zachary J. Williams, Kindle Song, Xiaojie Liu, Xiaohui Manthiram, Karthish Massachusetts Institute of Technology. Department of Chemical Engineering We report a direct and efficient electrochemical carboxylation of benzylic C-N bonds with CO₂ at room temperature. The reaction has been successfully applied to both primary and secondary benzylic C-N bonds with the compatibility of a variety of functional groups. This procedure does not require stoichiometric metals, external reducing agents, or sacrificial anodes, making column chromatography unnecessary for product purification. Differential electrochemical mass spectrometry (DEMS) was used to elucidate key intermediates of the electrocarboxylation reaction. 2020-06-12T20:40:14Z 2020-06-12T20:40:14Z 2019-04 2019-04 2020-06-08T14:56:00Z Article http://purl.org/eprint/type/JournalArticle 2155-5435 https://hdl.handle.net/1721.1/125787 Yang, Deng-Tao et al. "Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide." ACS Catalysis 9, 5 (April 2019): 4699–4705 © 2019 American Chemical Society en http://dx.doi.org/10.1021/acscatal.9b00818 ACS Catalysis Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) Prof. Manthiram via Ye Li |
| spellingShingle | Yang, Dengtao Zhu, Minghui Schiffer, Zachary J. Williams, Kindle Song, Xiaojie Liu, Xiaohui Manthiram, Karthish Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide |
| title | Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide |
| title_full | Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide |
| title_fullStr | Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide |
| title_full_unstemmed | Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide |
| title_short | Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide |
| title_sort | direct electrochemical carboxylation of benzylic c n bonds with carbon dioxide |
| url | https://hdl.handle.net/1721.1/125787 |
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