- Photoredox activation of carbon dioxide for amino acid synthesis in continuous flow
-
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.
- Seo, Hyowon,Katcher, Matthew H.,Jamison, Timothy F.
-
p. 453 - 456
(2017/05/05)
-
- The highly stereoselective formation of pipecolic acid N-oxide and related derivatives
-
N-Alkylated derivatives of pipecolic acid are shown to undergo highly stereoselective oxidation to give stable tertiary amine N-oxides. The ester derivatives show a high degree of stability compared to their proline analogues.
- O'Neil, Ian A.,Potter, Andrew J.
-
p. 5731 - 5734
(2007/10/03)
-