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Visible-Light-Driven CarboxyLic Amine Protocol (CLAP) for the Synthesis of 2‑Substituted Piperazines under Batch and Flow Conditions

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journal contribution
posted on 2020-06-24, 00:13 authored by Robin Gueret, Lydie Pelinski, Till Bousquet, Mathieu Sauthier, Vincent Ferey, Antony Bigot
Piperazines are privileged scaffolds in medicinal chemistry. Disclosed herein is a visible-light-promoted decarboxylative annulation protocol between a glycine-based diamine and various aldehydes to access 2-aryl, 2-heteroaryl, as well as 2-alkyl piperazines. The iridium-based complex [Ir­(ppy)2(dtbpy)]­PF6 and carbazolyl dicyanobenzene 4CzIPN were found to be the photocatalysts of choice to efficiently perform the transformation under mild conditions, whether in batch or in continuous mode.

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