4.8 Article

N-Heterocyclic-Carbene-Catalyzed Synthesis of 2-Aryl Indoles

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 36, Pages 9603-9607

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405035

Keywords

asymmetric synthesis; cooperative effects; carbenes

Funding

  1. NIH [R01-GM073072]
  2. Northwestern University

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A convergent and efficient transition-metal-free catalytic synthesis of 2-aryl-indoles has been developed. The interception of a highly reactive and transient aza-ortho-quinone methide by an acyl anion equivalent generated through N-hetereocyclic carbene catalysis is central to this successful strategy. High yields and a wide scope as well as the streamlined synthesis of a kinase inhibitor are reported.

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