Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination
Type
ArticleAuthors
Liu, XiangqianHsiao, Chien-Chi
Kalvet, Indrek
Leiendecker, Matthias
Guo, Lin
Schoenebeck, Franziska
Rueping, Magnus

KAUST Department
Chemical Science ProgramKAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2016-04-08Online Publication Date
2016-04-08Print Publication Date
2016-05-10Permanent link to this record
http://hdl.handle.net/10754/623142
Metadata
Show full item recordAbstract
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.Citation
Liu X, Hsiao C-C, Kalvet I, Leiendecker M, Guo L, et al. (2016) Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination. Angewandte Chemie International Edition 55: 6093–6098. Available: http://dx.doi.org/10.1002/anie.201510497.Sponsors
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).Publisher
WileyJournal
Angewandte Chemieae974a485f413a2113503eed53cd6c53
10.1002/anie.201510497