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Direct Electrochemical Carboxylation of Benzylic C–N Bonds with Carbon Dioxide

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acscatal.9b00818DOIArticle
ORCID:
AuthorORCID
Yang, Deng-Tao0000-0002-8315-5467
Zhu, Minghui0000-0003-1593-9320
Schiffer, Zachary J.0000-0001-6069-8613
Williams, Kindle0000-0001-9640-7849
Manthiram, Karthish0000-0001-9260-3391
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.
Funders:
Funding AgencyGrant Number
Massachusetts Institute of Technology (MIT)UNSPECIFIED
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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