Synthesis of Dihydropyrazoles via Palladium-Catalyzed Cascade Heterocyclization/Carbonylation/Arylation of β,γ-Unsaturated N-Tosyl Hydrazones

Author(s)

Dantas, Juliana A. ; Hardy, Melissa A. ; Costa, Mateus O. ; De Oliveira, Camila P. ; Cabral, Tadeu L. G. ; Tormena, Claudio Francisco ; Sigman, Matthew S. ; Ferreira, Marco A. B.

• Document type: Journal article
• Source: ADVANCED SYNTHESIS & CATALYSIS; v. 366, n. 5, p. 8-pg., 2023-12-21.

Abstract

A Pd-catalyzed heterocyclization/carbonylation/arylation cascade reaction between beta,gamma-unsaturated N-Ts hydrazones and commercially available arylboronic acids as coupling partners is described, producing 2-pyrazoline-ketone derivatives in 11-78% yield. A detailed statistical analysis of reactivity patterns of boronic acids provided key information about the limitations of the method, highlighting the challenges of degradation pathways. Our methodology offers a tool for synthesizing diverse 2-pyrazoline-ketone derivatives, expanding the toolbox of accessible N-N-heterocycles. (AU)

• FAPESP's process: 22/11314-5 - Data-driven catalyst design: methodological development and mechanistic studies
• Grantee: Marco Antonio Barbosa Ferreira
• Support Opportunities: Regular Research Grants
• FAPESP's process: 21/12394-0 - Sustainable synthetic methods employing catalysis, benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 20/10246-0 - Nuclear magnetic resonance spectroscopy: from pulse sequences to structural assignments
• Grantee: Claudio Francisco Tormena
• Support Opportunities: Research Projects - Thematic Grants