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Rhodium(III) and Hexabromobenzene—A Catalyst System for the Cross-Dehydrogenative Coupling of Simple Arenes and Heterocycles with Arenes Bearing Directing Groups

Authors


  • We thank Nadine Kuhl and Prof. Frederic W. Patureau for helpful discussions, Cornelia Weitkamp for valuable help, and Dr. Klaus Bergander for special NMR experiments. This work was supported by the European Research Council under the European Community’s Seventh Framework Program (FP7 2007-2013)/ERC Grant agreement no. 25936, and the Government of North Rhine-Westphalia in the research network SusChemSys. The research of F.G. has been supported by the Alfried Krupp Prize for Young University Teachers of the Alfried Krupp von Bohlen und Halbach Foundation.

Abstract

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C6Brsix & drugs! C6Br6 can be used as the cooxidant/catalyst modifier for the [RhIIICp*]-catalyzed (Cp*=C5Me5) dehydrogenative cross-coupling of benzamides with simple benzene derivatives (see scheme, DG=directing group). Similarly, heterocycles can be coupled and druglike structures formed. Mechanistic studies suggest a unique and multiple role of the Cu(OAc)2/C6Br6 system and a nonchelate-assisted C[BOND]H activation as the rate-determing step.

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