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N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles.

ABSTRACT: 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.

SUBMITTER: Hovey MT

PROVIDER: S-EPMC4164393 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles.

Hovey M Todd MT Check Christopher T CT Sipher Alexandra F AF Scheidt Karl A KA

Angewandte Chemie (International ed. in English) 20140714 36

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. ...[more]

PMID: 25044815

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