Ruthenium-catalyzed hydroaroylation of styrenes in water through directed C-H bond activation

Anis Tlili, Johannes Schranck, Jola Pospech, Helfried Neumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Selective C-H bond-functionalization reactions of arenes offer the potential for a more benign synthesis of fine chemicals and organic building blocks for the life science industries. In this respect, direct carbonylative coupling reactions of (hetero)arenes allow for the straightforward synthesis of (hetero)aromatic ketones and related derivatives. Herein, we present an efficient ruthenium(II)-catalyzed carbonylative hydroarylation of alkenes through directed C-H functionalization. More specifically, the carbonylative hydroarylation of styrenes with 2-aryl- (heteroaryl)pyridines and related derivatives proceeds selectively and with 100 % atom efficiency in water as the solvent. Three-Component Hydroaroylation: Hydroaroylation through C-H activation of (hetero)arenes bearing ortho-directing groups (DGs) proceeds in the presence of a ruthenium catalyst, carbon monoxide, and styrenes. The shown coupling process provides selective and atom-economic access to (hetero)- aromatic ketones.

Original languageEnglish
Pages (from-to)1562-1566
Number of pages5
JournalChemCatChem
Volume6
Issue number6
DOIs
StatePublished - Jun 2014
Externally publishedYes

Keywords

  • C-H activation
  • carbonylation
  • hydroaroylation
  • ruthenium
  • water

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