Selective Monoarylation of Aromatic Ketones and Esters via Cleavage of Aromatic Carbon-Heteroatom Bonds by Trialkylphosphine Ruthenium Catalysts

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Abstract

We report here the ruthenium-catalyzed selective monoarylation of aromatic ketones bearing two ortho carbon-heteroatom (O or N) bonds. Under the newly developed catalyst system consisting of RuHCl(CO)(PiPr3)2, CsF, and styrene, the C-O arylation of 2′,6′-dimethoxyacetophenone with a phenylboronate gave the C-O monoarylation product selectively. The selective C-O monoarylation was applicable to a variety of arylboronates and aromatic ketones and proceeds with high regio- and chemoselectivities. A formal synthesis of altertenuol was also achieved using the C-O monoarylation of an aromatic ester as a key step.

Original languageEnglish
Pages (from-to)794-797
Number of pages4
JournalOrganic Letters
Volume19
Issue number4
DOIs
Publication statusPublished - 2017 Feb 17

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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