title: Hydrohalogenative aromatization of multiynes promoted by ruthenium alkylidene complexes.
abstract: A new functionalization method of arynes promoted by a novel catalytic role of the Grubbs-type ruthenium alkylidene complex is described. Through a sequence of aryne formation followed by their halo-functionalization, various bis-1,3-diynes were directly converted to functionalized aryl chlorides, bromides and iodides in good yields in the presence of a catalytic amount of a ruthenium alkylidene complex and halogenated hydrocarbons such as CH2Cl2, CHCl3, CH2Br2, and CH2I2. The utility of this novel transformation is demonstrated by a formal synthesis of herbindole B.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dsunglee@uic.edu.
authors.forename: Rajdip
authors.initials: R
authors.lastname: Karmakar
authors.forename: Kung-Pern
authors.initials: KP
authors.lastname: Wang
authors.forename: Sang Young
authors.initials: SY
authors.lastname: Yun
authors.forename: Phani
authors.initials: P
authors.lastname: Mamidipalli
authors.forename: Daesung
authors.initials: D
authors.lastname: Lee
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D054879:Halogenation; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
chemical_list: D000480:Alkynes; D006841:Hydrocarbons, Aromatic; D009942:Organometallic Compounds; D012428:Ruthenium