Chemistry on-the-fly is an interesting concept, extensively studied in recent years due to its potential use for recognition, quantification and conversion of chemical species in solution. In this context, chemistry on-the-fly for asymmetric synthesis is a promising field of investigation, since it can help to overcome mass transport limitations, present for example in conventional organic electrosynthesis. Herein, the synergy between a magnetic field-enhanced self-electrophoretic propulsion mechanism and enantioselective redox chemistry on-the-fly is proposed as an efficient concept to boost the stereoselective conversion. We employ Janus swimmers as redox-active elements, exhibiting a well-controlled clockwise or anticlockwise motion with a speed that can be increased by one order of magnitude in the presence of an external magnetic field. While moving, these bifunctional objects convert spontaneously on-the-fly a prochiral molecule into a specific enantiomer with high enantiomeric excess. The magnetic field-enhanced self-mixing of the swimmers, based on the formation of local magnetohydrodynamic vortices, leads to an significant improvement of the reaction yield and the conversion rate.

Magnetic field-enhanced redox chemistry on-the-fly for enantioselective synthesis / G. Salinas, S. Arnaboldi, P. Garrigue, G. Bonetti, R. Cirilli, T. Benincori, A. Kuhn. - In: FARADAY DISCUSSIONS. - ISSN 1359-6640. - (2023), pp. 1-8. [Epub ahead of print] [10.1039/D3FD00041A]

Magnetic field-enhanced redox chemistry on-the-fly for enantioselective synthesis

S. Arnaboldi
Secondo
;
2023

Abstract

Chemistry on-the-fly is an interesting concept, extensively studied in recent years due to its potential use for recognition, quantification and conversion of chemical species in solution. In this context, chemistry on-the-fly for asymmetric synthesis is a promising field of investigation, since it can help to overcome mass transport limitations, present for example in conventional organic electrosynthesis. Herein, the synergy between a magnetic field-enhanced self-electrophoretic propulsion mechanism and enantioselective redox chemistry on-the-fly is proposed as an efficient concept to boost the stereoselective conversion. We employ Janus swimmers as redox-active elements, exhibiting a well-controlled clockwise or anticlockwise motion with a speed that can be increased by one order of magnitude in the presence of an external magnetic field. While moving, these bifunctional objects convert spontaneously on-the-fly a prochiral molecule into a specific enantiomer with high enantiomeric excess. The magnetic field-enhanced self-mixing of the swimmers, based on the formation of local magnetohydrodynamic vortices, leads to an significant improvement of the reaction yield and the conversion rate.
Settore CHIM/01 - Chimica Analitica
2023
22-mar-2023
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/968949
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