title: Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C-O Bond Activation of Aryl and Enol Ethers.
abstract: A nickel-catalyzed alkylation of polycyclic aromatic methyl ethers as well as methyl enol ethers with B-alkyl 9-BBN and trialkylborane reagents that involves the cleavage of stable C(sp2)-OMe bonds is described. The transformation has a wide substrate scope and good chemoselectivity profile while proceeding under mild reaction conditions; it provides a versatile way to form C(sp2)-C(sp3) bonds that does not suffer from β-hydride elimination. Furthermore, a selective and sequential alkylation process by cleavage of inert C-O bonds is presented to demonstrate the advantage of this method.
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: Xiangqian
authors.initials: X
authors.lastname: Liu
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Baumann
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.|King Abdullah University of Science and Technology (KAUST), KAUST Catalysis Center (KCC), Thuwal, 23955-6900, Saudi Arabia.
authors.forename: Magnus
authors.initials: M
authors.lastname: Rueping
keywords: C−O activation; alkylation; alkylboron reagents; aromatic methyl ethers; nickel catalysis