4.8 Article

α-MsO/TsO/Cl Ketones as Oxidized Alkyne Equivalents: Redox-Neutral Rhodium(III)-Catalyzed C-H Activation for the Synthesis of N-Heterocycles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 10, Pages 2754-2758

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201310272

Keywords

CH activation; isoquinolones; ketones; N-heterocycles; rhodium catalysis

Funding

  1. Alexander von Humboldt Foundation
  2. Sao Paulo Research Foundation [2013/14209-9]
  3. European Research Council (ERC) under the European Community [25936]
  4. DFG

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-Halo and pseudohalo ketones are used for the first time as C(sp(3))-based electrophiles in transition-metal-catalyzed CH activation and as oxidized alkyne equivalents in Rh-III-catalyzed redox-neutral annulations to generate diverse N-heterocycles. This transformation is efficient and scalable. Due to the mild reaction conditions, a variety of functional groups could be tolerated.

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