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

doi:10.1002/anie.201510497

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 journal › Article › peer-review

126 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 language	English (US)
Pages (from-to)	6093-6098
Number of pages	6
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	20
DOIs	https://doi.org/10.1002/anie.201510497 https://doi.org/10.1002/ange.201510497
State	Published - Apr 8 2016

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Liu, X., Hsiao, C.-C., Kalvet, I., Leiendecker, M., Guo, L., Schoenebeck, F., & Rueping, M. (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(20), 6093-6098. https://doi.org/10.1002/anie.201510497, https://doi.org/10.1002/ange.201510497

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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.",

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

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).",

year = "2016",

month = apr,

day = "8",

doi = "10.1002/anie.201510497",

language = "English (US)",

volume = "55",

pages = "6093--6098",

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Liu, X, Hsiao, C-C, Kalvet, I, Leiendecker, M, Guo, L, Schoenebeck, F & Rueping, M 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, vol. 55, no. 20, pp. 6093-6098. https://doi.org/10.1002/anie.201510497, https://doi.org/10.1002/ange.201510497

Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination. / Liu, Xiangqian; Hsiao, Chien-Chi; Kalvet, Indrek et al.
In: Angewandte Chemie International Edition, Vol. 55, No. 20, 08.04.2016, p. 6093-6098.

Research output: Contribution to journal › Article › peer-review

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PY - 2016/4/8

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AB - 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.

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

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