title: Co-catalyzed cross-coupling of alkyl halides with tertiary alkyl Grignard reagents using a 1,3-butadiene additive.
abstract: The cobalt-catalyzed cross-coupling of alkyl (pseudo)halides with alkyl Grignard reagents in the presence of 1,3-butadiene as a ligand precursor and LiI is described. Sterically congested quaternary carbon centers could be constructed by using tertiary alkyl Grignard reagents. This reaction proceeds via an ionic mechanism with inversion of stereochemistry at the reacting site of the alkyl halide and is compatible with various functional groups. The use of both 1,3-butadiene and LiI was essential for achieving high yields and high selectivities.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
authors.forename: Takanori
authors.initials: T
authors.lastname: Iwasaki
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Takagawa
authors.forename: Surya P
authors.initials: SP
authors.lastname: Singh
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Kuniyasu
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Kambe
mesh_terms: D002070:Butadienes / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D002070:Butadienes; D006846:Hydrocarbons, Halogenated; D009942:Organometallic Compounds; D003035:Cobalt; C031763:1,3-butadiene