title: Transition-metal-free BF3-mediated regioselective direct alkylation and arylation of functionalized pyridines using Grignard or organozinc reagents.
abstract: A formal regioselective cross-coupling of various pyridines with alkyl and aryl groups can be achieved by a BF3·OEt2-mediated addition of Grignard or organozinc reagents to pyridines bearing various substituents (chloro, bromo, cyano, vinyl, phenyl, carbethoxy, nitro, etc.) followed by an oxidative aromatization mediated by chloranil. Good regioselectivity and wide functional group tolerance make this method very versatile for the preparation of polyfunctional pyridines. No transition-metal catalyst is required in these coupling reactions.
authors.affiliation: Department of Chemistry, Ludwig-Maximilians-Universität , Butenandtstr. 5-13, 81377 Munich, Germany.
authors.forename: Quan
authors.initials: Q
authors.lastname: Chen
authors.forename: Xavier Mollat
authors.initials: XM
authors.lastname: du Jourdin
authors.forename: Paul
authors.initials: P
authors.lastname: Knochel
mesh_terms: D000478:Alkylation; D001895:Boron / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D028561:Transition Elements / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
chemical_list: D011725:Pyridines; D028561:Transition Elements; D005461:Fluorine; D015032:Zinc; D001895:Boron