title: Ruthenium-catalyzed stereoselective anti-Markovnikov-addition of thioamides to alkynes.
abstract: A catalyst system generated in situ from bis(2-methallyl)-cycloocta-1,5-diene-ruthenium(II) and a phosphine was found to efficiently catalyze the addition of thioamides to terminal alkynes with exclusive formation of the anti-Markovnikov thioenamide products. The stereoselectivity of the addition is usually high and controlled by the choice of the phosphine ligand, whereas the (E)-isomers are predominantly formed in the presence of tri(n-octyl)phosphine, the use of bis(dicyclohexylphosphino)methane preferentially leads to the formation of the (Z)-configured thioenamides.
authors.affiliation: Fachbereich Chemie, TU Kaiserslautern, Erwin-Schrödinger-Strasse, Building 54, D-67663 Kaiserslautern, Germany. goossen@chemie.uni-kl.de
authors.forename: Lukas J
authors.initials: LJ
authors.lastname: Goossen
authors.forename: Mathieu
authors.initials: M
authors.lastname: Blanchot
authors.forename: Kifah S M
authors.initials: KS
authors.lastname: Salih
authors.forename: Ralf
authors.initials: R
authors.lastname: Karch
authors.forename: Andreas
authors.initials: A
authors.lastname: Rivas-Nass
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013854:Thioamides / Q000737:chemistry*
chemical_list: D000480:Alkynes; D013438:Sulfhydryl Compounds; D013854:Thioamides; D012428:Ruthenium