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

Handle URI:
http://hdl.handle.net/10754/623142
Title:
Lewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Elimination
Authors:
Liu, Xiangqian; Hsiao, Chien-Chi; Kalvet, Indrek; Leiendecker, Matthias; Guo, Lin; Schoenebeck, Franziska; Rueping, Magnus ( 0000-0003-4580-5227 )
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.
KAUST Department:
KAUST Catalysis Center (KCC)
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.
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
10-Apr-2016
DOI:
10.1002/anie.201510497; 10.1002/ange.201510497
Type:
Article
ISSN:
1433-7851
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).
Appears in Collections:
Articles; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorLiu, Xiangqianen
dc.contributor.authorHsiao, Chien-Chien
dc.contributor.authorKalvet, Indreken
dc.contributor.authorLeiendecker, Matthiasen
dc.contributor.authorGuo, Linen
dc.contributor.authorSchoenebeck, Franziskaen
dc.contributor.authorRueping, Magnusen
dc.date.accessioned2017-04-13T11:50:57Z-
dc.date.available2017-04-13T11:50:57Z-
dc.date.issued2016-04-10en
dc.identifier.citationLiu 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.en
dc.identifier.issn1433-7851en
dc.identifier.doi10.1002/anie.201510497en
dc.identifier.doi10.1002/ange.201510497en
dc.identifier.urihttp://hdl.handle.net/10754/623142-
dc.description.abstractIn 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.en
dc.description.sponsorshipX.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).en
dc.publisherWiley-Blackwellen
dc.subjectC-C cross-couplingen
dc.subjectC-O bond activationen
dc.subjectcross-couplingen
dc.subjectnickelen
dc.subjecttrialkylaluminumen
dc.titleLewis Acid Assisted Nickel-Catalyzed Cross-Coupling of Aryl Methyl Ethers by C−O Bond-Cleaving Alkylation: Prevention of Undesired β-Hydride Eliminationen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalAngewandte Chemie International Editionen
dc.contributor.institutionInstitute of Organic Chemistry; RWTH Aachen University; Landoltweg 1 52074 Aachen Germanyen
kaust.authorRueping, Magnusen
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