title: Chemoselective sp2-sp3 cross-couplings: iron-catalyzed alkyl transfer to dihaloaromatics.
abstract: The chemoselective functionalization of a range of dihaloaromatics with methyl, cyclopropyl, and higher alkyl Grignard reagents via iron-catalyzed cross-coupling is described. The site selectivity of C-X (X = halogen) activation is determined by factors such as the position of the halogen on the ring, the solvent, and the nucleophile. A one-pot protocol for the chemoselective synthesis of mixed dialkyl heterocycles is achieved solely employing iron catalysis.
authors.affiliation: Genentech Inc., Small Molecule Process Chemistry, 1 DNA Way, South San Francisco, California 94080, USA. malhotra.sushant@gene.com
authors.forename: Sushant
authors.initials: S
authors.lastname: Malhotra
authors.forename: Pamela S
authors.initials: PS
authors.lastname: Seng
authors.forename: Stefan G
authors.initials: SG
authors.lastname: Koenig
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Deese
authors.forename: Kevin A
authors.initials: KA
authors.lastname: Ford
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000473:Alkanes; D003432:Cross-Linking Reagents; D006219:Halogens; D006846:Hydrocarbons, Halogenated; D007501:Iron