Functional group-directed ortho-arylation of aromatic rings catalyzed by transition metal complexes

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Abstract

Ortho selective direct arylation reactions have been developed using coordination of functional groups to metal complexes. The reaction of 2-arylpyridines with arylstannanes in the presence of rhodium complexes afforded the desired ortho arylated products efficiently. The use of aryl halides also afforded the ortho arylated products by use of ruthenium catalyst. The ruthenium-cat- alyzed arylation was successfully expanded to 2-alkenylpyridines affording (Z)-β-arylated prod- ucts selectively. Allylic acetates can be also used in the ruthenium-catalyzed direct coupling reac- tion of 2-arylpyridines giving the ortho allylated products. On the other hand, the reaction of 2-aryloxazolines with certain allylic acetates gave homo coupling products at their ortho positions.

Original languageEnglish
Pages (from-to)229-238
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume67
Issue number3
DOIs
Publication statusPublished - 2009 Mar

Keywords

  • Allylation
  • Arylation
  • Atom efficiency
  • C-h bond cleavage
  • Cross-coupling
  • Directing group
  • Homocoupling
  • Ortho selectivity
  • Transition metal catalyst

ASJC Scopus subject areas

  • Organic Chemistry

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