Iridium-Catalyzed Regio- and Diastereoselective Synthesis of C-Substituted Piperazines
| Autor: | Luis Tarifa, M. Pilar del Río, Laura Asensio, José A. López, Miguel A. Ciriano, Ana M. Geer, Cristina Tejel |
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| Přispěvatelé: | Ministerio de Ciencia, Innovación y Universidades (España), European Commission, Agencia Estatal de Investigación (España), Gobierno de Aragón |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | ACS Catalysis. 13:3148-3152 |
| ISSN: | 2155-5435 |
| DOI: | 10.1021/acscatal.2c05895 |
| Popis: | Piperazine rings are essential motifs frequently found in commercial drugs. However, synthetic methodologies are mainly limited to N-substituted piperazines, preventing structural diversity. Disclosed herein is a straightforward catalytic method for the synthesis of complex C-substituted piperazines based on an uncommon head-to-head coupling of easily prepared imines. This 100% atom-economic process allows the selective formation of a sole diastereoisomer, a broad substrate scope, and a good functional group tolerance employing a bench-stable iridium catalyst under mild reaction conditions. Key to the success is the addition of N-oxides to the reaction mixture, as they notably enhance the catalytic activity and selectivity. The generous financial support from MCIN/AEI/10.13039/501100011033 (PID2020-119512GB-I00) and Gobierno de Aragón/FEDER, EU (GA/FEDER, Reactivity and Catalysis Inorganic Chemistry Group, E50_20D) is gratefully acknowledged. A.M.G. is thankful for Grant IJC2018-035231-I funded by MCIN/AEI/10.13039/501100011033, and L.T. thanks MICIIN/FEDER for an FPI fellowship. |
| Databáze: | OpenAIRE |
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