Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow

Hyowon Seo, Matthew H. Katcher, Timothy F. Jamison

Research output: Contribution to journalArticlepeer-review

169 Scopus citations

Abstract

Although carbon dioxide (CO 2) 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 CO 2 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 CO 2 and amines via the single-electron reduction of CO 2 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 CO 2 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.

Original languageEnglish (US)
Pages (from-to)453-456
Number of pages4
JournalNature chemistry
Volume9
Issue number5
DOIs
StatePublished - May 1 2017

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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