A Rh -catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored. The requirement of fluorinated diazomalonate was explored for this transformation. The developed methodology was further extended with the synthesis of the bioactive compound.
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Rh -Catalyzed Synthesis of Highly Substituted 2-Pyridones using Fluorinated Diazomalonate.
Chem Asian J
February 2020
Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, 721302, India.
A Rh -catalyzed strategy was developed for the rapid construction of highly substituted 2-pyridone scaffolds using α,β-unsaturated oximes and fluorinated diazomalonate. The reaction proceeds through direct, site-selective alkylation based on migratory insertion and subsequent cyclocondensation. A wide substrate scope with different functional groups was explored.
View Article and Find Full Text PDF[Rh(Cp*)]-catalyzed arylfluorination of α-diazoketoesters for facile synthesis of α-aryl-α-fluoroketoesters.
Org Biomol Chem
January 2019
State Key Laboratory for Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.
Here we describe the Cp*Rh(iii)-catalyzed cascade arylfluorination reactions of α-diazoketoesters with arylboronic acids and N-fluorobenzenesulfonimide for one-pot C(sp3)-C(aryl) and C(sp3)-F bond formation. The arylfluorination reaction can be accomplished with remarkable chemo- and regioselectivity. Our mechanistic investigation showed that the Rh-catalyzed arylfluorination of diazoacetates occurred by (1) transmetalation of arylboronic acids to form an arylrhodium(iii) complex, (2) coupling of diazomalonates with the arylrhodium(iii) complex to form carbene-rhodium, (3) migratory carbene insertion to form a diketonato-rhodium(iii) complex - probably via rearrangement of the putative σ-alkylrhodium(iii) complex, and (4) electrophilic fluorination of the diketonato-rhodium to form the α-aryl-α-fluoromalonates.
View Article and Find Full Text PDFDirect Difluoromethylation of Alcohols with an Electrophilic Difluoromethylated Sulfonium Ylide.
Angew Chem Int Ed Engl
July 2016
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
A general method for the formation of alkyl difluoromethylethers under mild reaction conditions and with good functional-group tolerance was developed. The development of the method was based on the invention of a stable, electrophilic, difluoromethylating reagent, difluoromethyl-(4-nitrophenyl)-bis(carbomethoxy) methylide sulfonium ylide, which was synthesized by reaction of the easily available 4-nitrophenyl (difluoromethyl)thioether and dimethyl diazomalonate in the presence of a rhodium catalyst.
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