Iridium-Catalyzed Regio- and Diastereoselective Synthesis of C-Substituted Piperazines

Tarifa, L. ; Río, M. P. del ; Asensio, L. ; López, J. A. (Universidad de Zaragoza) ; Ciriano, M. A. ; Geer, A. M. (Universidad de Zaragoza) ; Tejel, C.

Resumen: 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.

Idioma: Inglés

DOI: 10.1021/acscatal.2c05895

Año: 2023

Publicado en: ACS CATALYSIS 13, 5 (2023), 3148-3152
ISSN: 2155-5435

Factor impacto JCR: 11.7 (2023)

Categ. JCR: CHEMISTRY, PHYSICAL rank: 21 / 178 = 0.118 (2023) - Q1 - T1

Factor impacto CITESCORE: 20.8 - Chemistry (all) (Q1) - Catalysis (Q1)

Factor impacto SCIMAGO: 3.847 - Chemistry (miscellaneous) (Q1) - Catalysis (Q1)

Financiación: info:eu-repo/grantAgreement/ES/AEI/PID2020-119512GB-I00
Financiación: info:eu-repo/grantAgreement/ES/DGA/E50-20D
Financiación: info:eu-repo/grantAgreement/ES/MICINN/IJC-2018-035231-I

Tipo y forma: Artículo (Versión definitiva)

Área (Departamento): Área Química Inorgánica (Dpto. Química Inorgánica)