title: Rhodium-catalyzed intramolecular hydroarylation of 1-halo-1-alkynes: regioselective synthesis of semihydrogenated aromatic heterocycles.
abstract: The regioselective intramolecular hydroarylation of (3-halo-2-propynyl)anilines, (3-halo-2-propynyl) aryl ethers, or (4-halo-3-butynyl) aryl ethers was efficiently catalyzed by Rh2(OCOCF3)4 to give semihydrogenated aromatic heterocycles, such as 4-halo-1,2-dihydroquinolines, 4-halo-3-chromenes, or 4-(halomethylene)chromans, in good to excellent yields. Some synthetic applications taking advantage of the halo-substituents of the products are also illustrated.
authors.affiliation: Department of Biomolecular Engineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501 (Japan), Fax: (+81) (0)45-924-5849.
authors.forename: Hirohiko
authors.initials: H
authors.lastname: Murase
authors.forename: Kousuke
authors.initials: K
authors.lastname: Senda
authors.forename: Masato
authors.initials: M
authors.lastname: Senoo
authors.forename: Takeshi
authors.initials: T
authors.lastname: Hata
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Urabe
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006865:Hydrogenation; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D001578:Benzopyrans; D056831:Coordination Complexes; D006571:Heterocyclic Compounds; D011804:Quinolines; D012238:Rhodium
keywords: chromene; dihydroquinolines; heterocycles; hydroarylation; rhodium