title: The benzyne Fischer-indole reaction.
abstract: A new approach to the Fischer-indole synthesis is reported that uses the reactive intermediate benzyne. The addition of N-tosyl hydrazones to arynes, generated through fluoride activation of 2-(trimethylsilyl)phenyl triflate precursors, leads to efficient N-arylation. Addition of a Lewis acid to the same reaction pot then affords N-tosylindole products via Fischer cyclization.
authors.affiliation: University of Edinburgh, School of Chemistry, Joseph Black Building, King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, UK.
authors.forename: Donald
authors.initials: D
authors.lastname: McAusland
authors.forename: Sangwon
authors.initials: S
authors.lastname: Seo
authors.forename: Didier G
authors.initials: DG
authors.lastname: Pintori
authors.forename: Jonathan
authors.initials: J
authors.lastname: Finlayson
authors.forename: Michael F
authors.initials: MF
authors.lastname: Greaney
mesh_terms: D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006835:Hydrazones / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D014105:Tosyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001555:Benzene Derivatives; D006835:Hydrazones; D007211:Indoles; C493629:N-tosylindole; D014105:Tosyl Compounds; C524146:benzyne