title: Alkylation of pyridines at their 4-positions with styrenes plus yttrium reagent or benzyl Grignard reagents.
abstract: A new regioselective alkylation of pyridines at their 4-position was achieved with styrenes in the presence of yttrium trichloride, BuLi, and diisobutylaluminium hydride (DIBAL-H) in THF. Alternatively, similar products were more simply prepared from pyridines and benzyl Grignard reagents. These reactions are not only a useful preparation of 4-substituted pyridines but are also complementary to other relevant reactions usually giving 2-substituted pyridines.
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).
authors.forename: Tomoya
authors.initials: T
authors.lastname: Mizumori
authors.forename: Takeshi
authors.initials: T
authors.lastname: Hata
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Urabe
mesh_terms: D000478:Alkylation; D005663:Furans / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*; D015019:Yttrium / Q000737:chemistry*
chemical_list: D005663:Furans; D058116:Lewis Acids; D009942:Organometallic Compounds; D011725:Pyridines; D013343:Styrenes; C018674:tetrahydrofuran; D015019:Yttrium; C035719:diisobutylaluminum
keywords: Grignard reagents; alkylation; pyridine; regioselectivity; yttrium