Nickel-catalyzed cross-coupling of chromene acetals and boronic acids

Thomas J.A. Graham, Abigail G. Doyle

Research output: Contribution to journalArticle

59 Scopus citations

Abstract

A modular and highly efficient protocol for the synthesis of 2-aryl- and heteroaryl-2H-chromenes is described. Under base-free conditions, readily accessible 2-ethoxy-2H-chromenes undergo C sp3-O activation and C sp3-C bond formation in the presence of an inexpensive nickel catalyst and boronic acids. This new strategy enables broad access to 2-substituted-2H-chromenes and has been applied to the late-stage incorporation of complex molecules, including the pharmaceuticals loratidine and indomethacin methyl ester.

Original languageEnglish (US)
Pages (from-to)1616-1619
Number of pages4
JournalOrganic letters
Volume14
Issue number6
DOIs
StatePublished - Mar 16 2012

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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