A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C–H Activation
2013; American Chemical Society; Volume: 135; Issue: 14 Linguagem: Inglês
10.1021/ja402274g
ISSN1943-2984
AutoresTodd K. Hyster, Kyle E. Ruhl, Tomislav Rovis,
Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoThe 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.
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