Yang, Deng-Tao and Zhu, Minghui and Schiffer, Zachary J. and Williams, Kindle and Song, Xiaojie and Liu, Xiaohui and Manthiram, Karthish (2019) Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide. ACS Catalysis, 9 (5). pp. 4699-4705. ISSN 2155-5435. doi:10.1021/acscatal.9b00818. https://resolver.caltech.edu/CaltechAUTHORS:20220505-565287000
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Abstract
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.
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| Alternate Title: | Direct Electrochemical Carboxylation of Benzylic C-N Bonds with Carbon Dioxide | ||||||||||||
| Additional Information: | © 2019 American Chemical Society. Received2 4 February 2019. Revised 6 April 2019. Published online 11 April 2019. Published in issue 3 May 2019. We gratefully acknowledge financial support from the MIT Energy Initiative Low Carbon Energy Center on Carbon Capture, Utilization, and Storage. We thank IKA for the donation of ElectraSyn 2.0. The authors declare no competing financial interest. | ||||||||||||
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| Subject Keywords: | electrochemistry; carboxylation; carbon dioxide; carboxylic acids; C−N bond | ||||||||||||
| Issue or Number: | 5 | ||||||||||||
| DOI: | 10.1021/acscatal.9b00818 | ||||||||||||
| Record Number: | CaltechAUTHORS:20220505-565287000 | ||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20220505-565287000 | ||||||||||||
| Official Citation: | Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide Deng-Tao Yang, Minghui Zhu, Zachary J. Schiffer, Kindle Williams, Xiaojie Song, Xiaohui Liu, and Karthish Manthiram ACS Catalysis 2019 9 (5), 4699-4705 DOI: 10.1021/acscatal.9b00818 | ||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
| ID Code: | 114619 | ||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||
| Deposited By: | George Porter | ||||||||||||
| Deposited On: | 06 May 2022 22:56 | ||||||||||||
| Last Modified: | 06 May 2022 22:56 |
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