title: Phosphinic Amide as Directing Group Enabling Palladium(II)-Catalyzed ortho C-H Alkenylation of Anilines without and with Alkylation at the Nitrogen Atom.
abstract: A phosphinic amide is introduced as a directing group for the ortho C-H alkenylation of anilines. The new donor group distinguishes itself from existing ones by assisting the C-H bond activation of anilides without (NH group) and with alkylation (NMe group) at the amide nitrogen atom. The reactivity is even reversed with the methyl-substituted anilide being more reactive than its unsubstituted counterpart. Electron-donating substituents at the arene ring enhance their reactivity while halogenation is not tolerated. The phosphinic amide also enables the C-7-selective C-H alkenylation of indoline.
authors.affiliation: Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany), Fax: (+49) 30-314-28829.
authors.forename: Lin-Yu
authors.initials: LY
authors.lastname: Jiao
authors.affiliation: Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany), Fax: (+49) 30-314-28829.
authors.forename: André V
authors.initials: AV
authors.lastname: Ferreira
authors.affiliation: Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623, Berlin, Germany), Fax: (+49) 30-314-28829. martin.oestreich@tu-berlin.de.
authors.forename: Martin
authors.identifier: http://orcid.org/0000-0002-1487-9218
authors.initials: M
authors.lastname: Oestreich
keywords: C−H activation; alkenylation; cross-dehydrogenative coupling; homogeneous catalysis; palladium