title: Branched Arylalkenes from Cinnamates: Selectivity Inversion in Heck Reactions by Carboxylates as Deciduous Directing Groups.
abstract: A decarboxylative Mizoroki-Heck coupling of aryl halides with cinnamic acids has been developed in which the carboxylate group directs the arylation into its β-position before being tracelessly removed through protodecarboxylation. In the presence of a copper/palladium catalyst, both electron-rich and electron-deficient aryl bromides and chlorides bearing numerous functionalities were successfully coupled with broadly available cinnamates, with selective formation of 1,1-disubstituted alkenes. This reaction concept, in which the carboxylate acts as a deciduous directing group, ideally complements traditional 1,2-selective Heck reactions of styrenes.
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse, Geb. 54, 67663, Kaiserslautern, Germany.
authors.forename: Jie
authors.initials: J
authors.lastname: Tang
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse, Geb. 54, 67663, Kaiserslautern, Germany.
authors.forename: Dagmar
authors.initials: D
authors.lastname: Hackenberger
authors.affiliation: FB Chemie-Organische Chemie, Technische Universität Kaiserslautern, Erwin-Schrödinger-Strasse, Geb. 54, 67663, Kaiserslautern, Germany. goossen@chemie.uni-kl.de.
authors.forename: Lukas J
authors.identifier: 0000-0002-2547-3037
authors.initials: LJ
authors.lastname: Goossen
keywords: Heck reaction; alkenes; carboxylic acids; copper; palladium