title: Fused ring construction around pyrrole, indole, and related compounds via palladium-catalyzed oxidative coupling with alkynes.
abstract: The selective synthesis of 1,2,3,4-tetrasubstituted carbazoles can be performed effectively through the palladium-catalyzed oxidative coupling reactions of N-substituted indoles or their carboxylic acid derivatives with alkynes. Unsymmetrically octasubstituted carbazoles can also be obtained by the stepwise couplings of 1-methylpyrrole-2-carboxylic acid with two different alkynes. In addition, the present coupling procedure is applicable to the synthesis of other various heteroarenes possessing di-, tri-, and tetracyclic cores. Some of the products exhibit intense fluorescence in the solid state.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
authors.forename: Mana
authors.initials: M
authors.lastname: Yamashita
authors.forename: Hakaru
authors.initials: H
authors.lastname: Horiguchi
authors.forename: Koji
authors.initials: K
authors.lastname: Hirano
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Satoh
authors.forename: Masahiro
authors.initials: M
authors.lastname: Miura
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D002264:Carboxylic Acids; D007211:Indoles; D011758:Pyrroles; D010165:Palladium