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Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes.

ABSTRACT: A convergent, transition-metal-free synthesis of 2-aryl-azaindoles has been developed. The interception of a reactive aza-ortho-azaquinone methide intermediate by an acyl anion equivalent generated through carbene catalysis provides high yields, a wide substrate scope, and the synthesis of previously inaccessible azaindoles.

SUBMITTER: Sharma HA

PROVIDER: S-EPMC4950954 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Azaindole synthesis through dual activation catalysis with N-heterocyclic carbenes.

Sharma Hayden A HA Todd Hovey M M Scheidt Karl A KA

Chemical communications (Cambridge, England) 20160701 59

A convergent, transition-metal-free synthesis of 2-aryl-azaindoles has been developed. The interception of a reactive aza-ortho-azaquinone methide intermediate by an acyl anion equivalent generated through carbene catalysis provides high yields, a wide substrate scope, and the synthesis of previously inaccessible azaindoles. ...[more]

PMID: 27363788

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