Copper-Catalyzed Continuous-Flow Transfer Hydrogenation of Nitroarenes to Anilines: A Scalable and Reliable Protocol

A robust supported catalyst that is made up of copper nanoparticles on Celite has been successfully prepared for the selective transfer hydrogenation of aromatic nitrobenzenes to anilines under continuous flow. The method is efficient and environmentally benign thanks to the absence of hydrogen gas...

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Veröffentlicht in:Organic process research & development 2024-05, Vol.28 (5), p.1515-1528
Hauptverfasser: Martina, Katia, Moran, Maria Jesus, Manzoli, Maela, Trukhan, Mikhail V., Kuhn, Simon, Van Gerven, Tom, Cravotto, Giancarlo
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container_end_page 1528
container_issue 5
container_start_page 1515
container_title Organic process research & development
container_volume 28
creator Martina, Katia
Moran, Maria Jesus
Manzoli, Maela
Trukhan, Mikhail V.
Kuhn, Simon
Van Gerven, Tom
Cravotto, Giancarlo
description A robust supported catalyst that is made up of copper nanoparticles on Celite has been successfully prepared for the selective transfer hydrogenation of aromatic nitrobenzenes to anilines under continuous flow. The method is efficient and environmentally benign thanks to the absence of hydrogen gas and precious metals. Long-term stability studies show that the catalytic system is able to achieve very high nitrobenzene conversion (>99%) when working for up to 145 h. The versatility of the transfer hydrogenation system has been tested using representative examples of nitroarenes, with moderate-to-excellent yields being obtained. The packed bed reactor (PBR) permits the use of a setup that can provide products via simple isolation by SPE without the need for further purification. The recovery and reuse of either EG or the ion-exchange resin leads to consistent waste reduction; therefore, E-factor distribution analysis has highlighted the environmental efficiency of this synthetic protocol.
doi_str_mv 10.1021/acs.oprd.3c00144
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title Copper-Catalyzed Continuous-Flow Transfer Hydrogenation of Nitroarenes to Anilines: A Scalable and Reliable Protocol
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