title: 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.
authors.affiliation: Department of Chemistry Center for Molecular Innovation and Drug Discovery, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA).
authors.forename: M Todd
authors.initials: MT
authors.lastname: Hovey
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Check
authors.forename: Alexandra F
authors.initials: AF
authors.lastname: Sipher
authors.forename: Karl A
authors.initials: KA
authors.lastname: Scheidt
mesh_terms: D001372:Aza Compounds / Q000737:chemistry; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007211:Indoles / Q000138:chemical synthesis*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D006571:Heterocyclic Compounds; D007211:Indoles; D047428:Protein Kinase Inhibitors; C030011:carbene; D008697:Methane
keywords: asymmetric synthesis; carbenes; cooperative effects