title: Mechanistic Study on Pd/Mono-N-protected Amino Acid Catalyzed Vinyl-Vinyl Coupling Reactions: Reactivity and E/Z Selectivity.
abstract: A combined mass spectrometric and computational study of the Pd/mono-N-protected amino acid (MPAA)-catalyzed vinyl-vinyl coupling reactions is reported. Computational study reveals that the reaction is initiated by C-H activation of the styrene followed by the insertion of acrylate. This is supported by mass spectrometry. The MPAA ligand facilitates the cross-coupling reaction between monosubstituted alkenes by stabilizing the active palladium catalyst and offering the N-protecting group as a stronger base than acetate. The E/Z selectivity is attributed to the stronger d-π interaction between the catalyst and the substrate in the transition state leading to E product.
authors.affiliation: Lab of Computational Chemistry and Drug Design, Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School , Shenzhen 518055, China.
authors.forename: Xiu-Mei
authors.initials: XM
authors.lastname: Zhong
authors.affiliation: Lab of Computational Chemistry and Drug Design, Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School , Shenzhen 518055, China.
authors.forename: Gui-Juan
authors.initials: GJ
authors.lastname: Cheng
authors.affiliation: Lab of Computational Chemistry and Drug Design, Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School , Shenzhen 518055, China.
authors.forename: Ping
authors.initials: P
authors.lastname: Chen
authors.affiliation: Lab of Computational Chemistry and Drug Design, Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School , Shenzhen 518055, China.
authors.forename: Xinhao
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Lab of Computational Chemistry and Drug Design, Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School , Shenzhen 518055, China.|College of Chemistry, Peking University , Beijing 100871, China.
authors.forename: Yun-Dong
authors.initials: YD
authors.lastname: Wu