dc.contributor.author | Seo, Hyowon | |
dc.contributor.author | Katcher, Matthew Herman | |
dc.contributor.author | Jamison, Timothy F | |
dc.date.accessioned | 2018-01-29T15:05:25Z | |
dc.date.available | 2018-01-29T15:05:25Z | |
dc.date.issued | 2016-12 | |
dc.date.submitted | 2016-09 | |
dc.identifier.issn | 1755-4330 | |
dc.identifier.issn | 1755-4349 | |
dc.identifier.uri | http://hdl.handle.net/1721.1/113316 | |
dc.description.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. | en_US |
dc.description.sponsorship | National Institute of General Medical Sciences (U.S.) (Award F32GM108181) | en_US |
dc.publisher | Nature Publishing Group | en_US |
dc.relation.isversionof | http://dx.doi.org/10.1038/NCHEM.2690 | en_US |
dc.rights | 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. | en_US |
dc.source | PMC | en_US |
dc.title | Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow | en_US |
dc.type | Article | en_US |
dc.identifier.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 | en_US |
dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
dc.contributor.mitauthor | Seo, Hyowon | |
dc.contributor.mitauthor | Katcher, Matthew Herman | |
dc.contributor.mitauthor | Jamison, Timothy F | |
dc.relation.journal | Nature Chemistry | en_US |
dc.eprint.version | Author's final manuscript | en_US |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
dc.date.updated | 2018-01-29T14:06:48Z | |
dspace.orderedauthors | Seo, Hyowon; Katcher, Matthew H.; Jamison, Timothy F. | en_US |
dspace.embargo.terms | N | en_US |
dc.identifier.orcid | https://orcid.org/0000-0002-9569-1902 | |
dc.identifier.orcid | https://orcid.org/0000-0002-0010-0496 | |
dc.identifier.orcid | https://orcid.org/0000-0002-8601-7799 | |
mit.license | PUBLISHER_POLICY | en_US |