Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow
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...
| Main Authors: | , , |
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| Format: | Article |
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Nature Publishing Group
2018
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| Online Access: | http://hdl.handle.net/1721.1/113316 https://orcid.org/0000-0002-9569-1902 https://orcid.org/0000-0002-0010-0496 https://orcid.org/0000-0002-8601-7799 |
| Summary: | 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. |
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