4.5 Article

C-H Bond Functionalization of Arylpyrimidines Catalyzed by an in situ Generated Ruthenium(II) Carboxylate System and the Construction of Tris(heteroaryl)-Substituted Benzenes

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 19, Pages 3474-3481

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100238

Keywords

C-H activation; Arylation; Pyrimidine; Carboxylate ligands; Ruthenium

Funding

  1. Ministry of Higher Education, Science and Technology of the Republic of Slovenia
  2. Slovenian Research Agency [P1-0230-0103]
  3. ENFIST Centre of Excellence

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A ruthenium(II) carboxylate catalyst, generated in situ from [RuCl2(p-cymene)](2) and 1-phenyl-1-cyclopentanecarboxylic acid (PCCA) in the presence of K2CO3, allowed activation of the C-H bond in phenyl-substituted pyrimidines and their direct functionalization with both electron-deficient and electron-rich aryl halides. The scope of this process can be extended to the use of heteroaryl bromides and less reactive aryl chlorides. This Ru-II-PCCA complex constitutes a better catalytic system in comparison to other carboxylates.

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