Palladium-catalyzed decarboxylative cross-coupling of α-oxocarboxylic acids and their derivatives

Jinmin Miao, Haibo Ge

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

The development of palladium(II)-catalyzed decarboxylative cross-coupling of α-oxocarboxylic acids and their derivatives is summarized in this account. Acetanilides, 2-phenyl-pyridines, and benzoic acids were found to be suitable substrates for direct acylation through decarboxylative cross-coupling with α-oxocarboxylic acids. Potassium aryl trifluoroborates were also transformed into ketones, amides, and esters with α-oxocarboxylic acids, oxamic acids, and oxalate monoesters, respectively, in modified catalytic systems. 1 Introduction 2 Palladium-Catalyzed Decarboxylative Cross-Coupling Through C-H Bond Functionalization 2.1 Direct ortho-Acylation of Acetanilides 2.2 Direct Acylation of 2-Phenylpyridines 2.3 Direct ortho-Acylation of Benzoic Acids 3 Transformation of Potassium Aryl Trifluoroborates into Ketones, Esters, and Amides 3.1 Formation of Aryl Ketones from Potassium Aryl Trifluoroborates 3.2 Preparation of Aryl Amides and Esters from Potassium Aryl Trifluoroborates 3.3 Mechanistic Studies 4 Conclusions and Outlook.

Original languageEnglish
Article number6587
Pages (from-to)911-919
Number of pages9
JournalSynlett
Volume25
Issue number7
DOIs
StatePublished - Apr 2014

Keywords

  • carbonylation
  • carboxylic acids
  • catalysis
  • cross-coupling
  • decarboxylation
  • palladium

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