Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination

Xiangqian Liu, Chien-Chi Hsiao, Indrek Kalvet, Matthias Leiendecker, Lin Guo, Franziska Schoenebeck, Magnus Rueping

Research output: Contribution to journalArticlepeer-review

124 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)6093-6098
Number of pages6
JournalAngewandte Chemie International Edition
Volume55
Issue number20
DOIs
StatePublished - Apr 8 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: X.L. and L.G. were supported by the China Scholarship Council, C.-C.H. was supported by a DAAD fellowship, and M.L. was supported by a Kekule fellowship (Fonds der Chemischen Industrie) and the Studienstiftung des deutschen Volkes. We gratefully acknowledge the computing time granted on the RWTH Bull Cluster in Aachen (JARA0091).

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