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.
Investigation of Petasis and Ugi reactions in series in an automated microreactor system
Petasis and Ugi reactions are used successively without intermediate purification, effectively accomplishing a six-component reaction. The examined reactions are transferred from traditional batch reactors to an automated continuous flow microreactor setu
Heublein, Norbert,Moore, Jason S.,Smith, Christopher D.,Jensen, Klavs F.
Synthesis and biological evaluation of benzimidazole derivatives as potent AMP-activated protein kinase activators
Design, synthesis and structure-activity relationships of benzimidazole derivatives as activators of the AMP-activated protein kinase (AMPK) are presented in this paper. AMPK is the central component of a protein kinase cascade that plays a key role in the regulation of energy balance. Once activated, AMPK initiates a series of responses that are aimed at restoring the energy balance of the cell and recent studies have indicated that AMPK plays an important role in regulation of the whole-body energy metabolism. The following study based on the lead compound S27847 involved modification of three regions of this compound. Preliminary structure-activity relationships are being described.
Charton, Julie,Girault-Mizzi, Sophie,Debreu-Fontaine, Marie-Ange,Foufelle, Fabienne,Hainault, Isabelle,Bizot-Espiard, Jean-Guy,Caignard, Daniel-Henri,Sergheraert, Christian
p. 4490 - 4518
(2007/10/03)
Diastereoselective Petasis Mannich reactions accelerated by hexafluoroisopropanol: A pyrrolidine-derived arylglycine synthesis
A diastereoselective synthesis of pyrrolidine-derived arylglycines has been developed using the Petasis boronic acid Mannich reaction. High diastereoselectivities in the reactions of chiral amines, aryl boronic acids, and glyoxylic acid monohydrate have been demonstrated for the first time. Key to the implementation of this method is the discovery that hexafluoroisopropanol accelerates the Petasis process, reducing reaction times from multiple days to less than 24 h.
Nanda, Kausik K.,Trotter, B. Wesley
p. 2025 - 2028
(2007/10/03)
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