Rapid construction of C4-substituted phenanthridinones through palladium-catalyzed domino N-arylation/aryl-aryl coupling process

An excellent chemo- and regioselective palladium-catalyzed cascade intermolecular N-arylation/aryl-aryl coupling process has been developed. Employing Pd(TFA)2, PCy3•HBF4, K2CO3 and 1,4-dioxane in an oil bath at 100°C for 12 h, diverse C4-substituted phenanthridinones are synthesized from o-bromobenzamides in 42-92% yield. Broad substrate scope and excellent functional group tolerance are observed. The synthetic utility of this method is illustrated by the further derivatization to prepare multiple-substituted phenanthridinones in 30-75% yield. © 2021

Authors
Liu C.1 , Song L.2 , Van Meervelt L. , Van Der Eycken E.V.
Journal
Molecular Catalysis
Publisher
Elsevier B.V.
Language
English
Status
Published
Link
External link
DOI
10.1016/J.MCAT.2021.111766
Number
111766
Volume
513
Year
2021
Organizations
  • 1 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 2 Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Nanjing, Jiangsu 210037, China
  • 3 Biomolecular Architecture, Department of Chemistry, KU Leuven Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 4 Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya street 6, Moscow, 117198, Russian Federation
Keywords
Aryl-aryl coupling; Arylation; Cyclization; Palladium; Phenanthridinone
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