A coupling of benzamides and donor/acceptor diazo compounds to form γ-lactams via Rh(III)-catalyzed C-H activation

Todd K. Hyster, Kyle E. Ruhl, Tomislav Rovis

Research output: Contribution to journalArticle

343 Scopus citations

Abstract

The coupling of O-pivaloyl benzhydroxamic acids with donor/acceptor diazo compounds provides isoindolones in high yield. The reaction tolerates a broad range of benzhydroxamic acids and diazo compounds, including substituted 2,2,2-trifluorodiazoethanes. Mechanistic experiments suggested that C-H activation is turnover-limiting and irreversible and that insertion of the diazo compound favors electron-deficient substrates.

Original languageEnglish (US)
Pages (from-to)5364-5367
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number14
DOIs
StatePublished - Apr 10 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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