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

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.

SUBMITTER: Hyster TK

PROVIDER: S-EPMC3658175 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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

Hyster Todd K TK Ruhl Kyle E KE Rovis Tomislav T

Journal of the American Chemical Society 20130402 14

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. ...[more]

PMID: 23548055

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