title: One-pot synthesis of 2,4-disubstituted indoles from N-tosyl-2,3-dichloroaniline using palladium-dihydroxyterphenylphosphine catalyst.
abstract: 4-Chloroindoles were synthesized from readily available 2,3-dichloroaniline derivatives and terminal alkynes. The catalyst composed of palladium and dicyclohexyl(dihydroxyterphenyl)phosphine (Cy-DHTP) enabled ortho-selective Sonogashira coupling, and subsequent cyclization afforded 4-chloroindoles in high yields. This transformation was successfully applied to the one-pot synthesis of 2,4-disubstituted indoles via Suzuki-Miyaura coupling after indole formation.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka , 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
authors.forename: Miyuki
authors.initials: M
authors.lastname: Yamaguchi
authors.forename: Kei
authors.initials: K
authors.lastname: Manabe
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013730:Terphenyl Compounds / Q000737:chemistry*
chemical_list: D000814:Aniline Compounds; D007211:Indoles; C000591755:N-tosyl-2,3-dichloroaniline; D010720:Phosphines; D013730:Terphenyl Compounds; C062517:4-chloroindole; D010165:Palladium