Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow
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Author(s)
Seo, Hyowon
Katcher, Matthew Herman
Jamison, Timothy F
Date Issued
December 2016
Journal
Nature Chemistry
Publisher
Nature Publishing Group
Citation
Seo, Hyowon et al. “Photoredox Activation of Carbon Dioxide for Amino Acid Synthesis in Continuous Flow.” Nature Chemistry 9, 5 (December 2016): 453–456 © 2017 Macmillan Publisher Limited part of Springer Nature
Version
Author's final manuscript
Abstract
Although carbon dioxide (CO₂) is highly abundant, its low reactivity has limited its use in chemical synthesis. In particular, methods for carbon-carbon bond formation generally rely on two-electron mechanisms for CO₂ activation and require highly activated reaction partners. Alternatively, radical pathways accessed via photoredox catalysis could provide new reactivity under milder conditions. Here we demonstrate the direct coupling of CO₂ and amines via the single-electron reduction of CO₂ for the photoredox-catalysed continuous flow synthesis of α-Amino acids. By leveraging the advantages of utilizing gases and photochemistry in flow, a commercially available organic photoredox catalyst effects the selective α-carboxylation of amines that bear various functional groups and heterocycles. The preliminary mechanistic studies support CO₂ activation and carbon-carbon bond formation via single-electron pathways, and we expect that this strategy will inspire new perspectives on using this feedstock chemical in organic synthesis.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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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.
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DOI of Published Version
https://doi.org/10.1038/NCHEM.2690
