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

Robin Gueret, Lydie Pelinski, Till Bousquet*, Mathieu Sauthier, Vincent Ferey and Antony Bigot*

*Univ. Lille, CNRS, Centrale Lille, ENSCL, Univ. Artois, UMR 8181, F-59000 Lille; Sanofi, 13 quai Jules Guesde, 94403 Vitry-Sur-Seine, France, Email: till.bousquetuniv-lille.fr, antony.bigotsanofi.com

R. Gueret, L. Pelinski, T. Bousquet, M. Sauthier, V. Ferey, A. Bigot, Org. Lett., 2020, 22, 5157-5162.

DOI: 10.1021/acs.orglett.0c01759

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Abstract

A visible-light-promoted decarboxylative annulation protocol between a glycine-based diamine and various aldehydes provides 2-aryl, 2-heteroaryl, as well as 2-alkyl piperazines under mild conditions. The iridium-based complex [Ir(ppy)₂(dtbpy)]PF₆ and carbazolyl dicyanobenzene 4CzIPN efficiently catalyze this transformation in batch or in continuous mode.

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Key Words

piperazines, photochemistry

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ID: J54-Y2020