title: Cobalt-catalyzed cross addition of silylacetylenes to internal alkynes.
abstract: A CoCl2·6H2O/Zn reagent using 2-(2,6-diisopropylphenyl)iminomethylpyridine (dipimp), 1,2-bis(diphenylphosphino)ethane (dppe), or 1,2-bis(diphenylphosphino)benzene (dppPh) as a ligand effectively catalyzed the cross-addition reaction of silylacetylene to internal alkynes. The reaction of some unsymmetrical internal alkynes, such as 3-arylpropargyl alcohols, proceeded in a highly regioselective manner in the presence of dppe or dppPh but gave a nearly 1:1 mixture of regioisomers in the presence of dipimp. The results of reactions using 1-deuterated 2-silylacetylene revealed that the reaction involves a direct oxidative addition of the silylacetylenic C-H bond to cobalt.
authors.affiliation: Department of Material and Life Chemistry, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Sakurada
authors.forename: Yu-ki
authors.initials: YK
authors.lastname: Sugiyama
authors.forename: Sentaro
authors.initials: S
authors.lastname: Okamoto
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: C519449:1,2-bis(diphenylphosphino)benzene; D000480:Alkynes; D001555:Benzene Derivatives; D007202:Indicators and Reagents; D008024:Ligands; D063065:Organophosphonates; D017646:Organosilicon Compounds; D003035:Cobalt