Development of catalytic methods to yield pharmacologically privileged hetereocycles promotes drug-discovery by facilitating compound synthesis and by offering new chemical scaffolds to probe therapeutic potential. Recently, 2-aryl-indoles have gained attention as potential drug molecules because of observed anti-microbial and anti-cancer activity. With this mollecular scaffold in mind, 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 wide substrate scope are observed. Additionally, a streamlined synthesis of a known kinase inhibitor is presented.

N-hetereocyclic carbene catalyzed synthesis of 2-aryl-Indoles

249th National Meeting (2015)

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