title: Silver-catalyzed regioselective carbomagnesiation of alkynes with alkyl halides and Grignard reagents.
abstract: A silver-catalyzed carbomagnesiation of alkynes with alkyl halides and Grignard reagents afforded alkenyl Grignard reagents regioselectively, where the alkyl group of the alkyl halide, but not that of the Grignard reagent, was introduced into the alkyne. Application to δ-haloalkylacetylenes yielded cyclopentanes or a tetrahydrofuran containing an exo-methylene substituent via 5-exo-dig cyclization.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871 Japan. kambe@chem.eng.osaka-u.ac.jp
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Kambe
authors.forename: Yuusuke
authors.initials: Y
authors.lastname: Moriwaki
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Fujii
authors.forename: Takanori
authors.initials: T
authors.lastname: Iwasaki
authors.forename: Jun
authors.initials: J
authors.lastname: Terao
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D003517:Cyclopentanes; D005663:Furans; D006846:Hydrocarbons, Halogenated; D009942:Organometallic Compounds; D012834:Silver; C018674:tetrahydrofuran