Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers

Lin Guo, Xiangqian Liu, Christoph Baumann, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

58 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)15415-15419
Number of pages5
JournalAngewandte Chemie International Edition
Volume55
Issue number49
DOIs
StatePublished - Nov 7 2016

Fingerprint Dive into the research topics of 'Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers'. Together they form a unique fingerprint.

Cite this