title: Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C-O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination.
abstract: In the presence of trialkylaluminum reagents, diverse aryl methyl ethers can be transformed into valuable products by C-O bond-cleaving alkylation, for the first time without the limiting β-hydride elimination. This new nickel-catalyzed dealkoxylative alkylation method enables powerful orthogonal synthetic strategies for the transformation of a variety of naturally occurring and easily accessible anisole derivatives. The directing and/or activating properties of aromatic methoxy groups are utilized first, before they are replaced by alkyl chains in a subsequent coupling process.
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Xiangqian
authors.initials: X
authors.lastname: Liu
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Chien-Chi
authors.initials: CC
authors.lastname: Hsiao
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Indrek
authors.initials: I
authors.lastname: Kalvet
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Leiendecker
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Lin
authors.initials: L
authors.lastname: Guo
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Franziska
authors.initials: F
authors.lastname: Schoenebeck
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany. magnus.rueping@rwth-aachen.de.|King Abdullah University of Science and Technology (KAUST), KAUST Catalysis Center (KCC), Thuwal, 23955-6900, Saudi Arabia. magnus.rueping@rwth-aachen.de.
authors.forename: Magnus
authors.initials: M
authors.lastname: Rueping
keywords: C−C cross-coupling; C−O bond activation; cross-coupling; nickel; trialkylaluminum