title: A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles.
abstract: A highly efficient method of indole synthesis using gem-dihalovinylaniline substrates and an organoboron reagent was developed via a Pd-catalyzed tandem intramolecular amination and an intermolecular Suzuki coupling. Aryl, alkenyl, and alkyl boron reagents are all successfully employed, making for a versatile modular approach. The reaction tolerates a variety of substitution patterns on the aniline leading to indoles with group at C2-C7. The orthogonal approach of the sequential copper- and palladium-mediated synthesis of 1,2-diarylindoles exploited the wide availability of diverse organoboron reagents.
authors.affiliation: Davenport Chemistry Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
authors.forename: Yuan-Qing
authors.initials: YQ
authors.lastname: Fang
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000814:Aniline Compounds; D001896:Boron Compounds; D007211:Indoles; D009578:Nitrobenzenes; C527428:gem-dihalovinylaniline; D010165:Palladium