An improved catalyst architecture for rhodium(iii) catalyzed C-H activation and its application to pyridone synthesis

Todd K. Hyster, Tomislav Rovis

Research output: Contribution to journalArticlepeer-review

162 Scopus citations

Abstract

We have developed a method for preparing pyridones from the coupling reaction of acrylamides and alkynes with either stoichometric Cu(OAc) 2 or catalytic Cu(OAc)2 and air as oxidants. In the course of these studies, it was found that a larger ligand, 1,3-di-tert- butylcyclopentadienyl (termed Cpt) results in higher degrees of regioselectivity in the alkyne insertion event. The transformation tolerates a broad variety of alkynes and acrylamides. Furthermore, Cpt and Cp* demonstrate similar catalytic activity. This similarity allows for mechanistic studies to be undertaken which suggest a difference in mechanism between this reaction and the previously studied benzamide system.

Original languageEnglish (US)
Pages (from-to)1606-1610
Number of pages5
JournalChemical Science
Volume2
Issue number8
DOIs
StatePublished - Aug 2011
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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