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

Handle URI:
http://hdl.handle.net/10754/623165
Title:
Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers
Authors:
Guo, Lin; Liu, Xiangqian; Baumann, Christoph; Rueping, Magnus ( 0000-0003-4580-5227 )
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.
KAUST Department:
KAUST Catalysis Center (KCC)
Citation:
Guo L, Liu X, Baumann C, Rueping M (2016) Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers. Angewandte Chemie International Edition 55: 15415–15419. Available: http://dx.doi.org/10.1002/anie.201607646.
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
7-Nov-2016
DOI:
10.1002/anie.201607646; 10.1002/ange.201607646
Type:
Article
ISSN:
1433-7851
Sponsors:
L.G. and X.L. were supported by the China Scholarship Council.
Additional Links:
http://onlinelibrary.wiley.com/doi/10.1002/anie.201607646/full
Appears in Collections:
Articles; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorGuo, Linen
dc.contributor.authorLiu, Xiangqianen
dc.contributor.authorBaumann, Christophen
dc.contributor.authorRueping, Magnusen
dc.date.accessioned2017-04-13T11:50:58Z-
dc.date.available2017-04-13T11:50:58Z-
dc.date.issued2016-11-07en
dc.identifier.citationGuo L, Liu X, Baumann C, Rueping M (2016) Nickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethers. Angewandte Chemie International Edition 55: 15415–15419. Available: http://dx.doi.org/10.1002/anie.201607646.en
dc.identifier.issn1433-7851en
dc.identifier.doi10.1002/anie.201607646en
dc.identifier.doi10.1002/ange.201607646en
dc.identifier.urihttp://hdl.handle.net/10754/623165-
dc.description.abstractA 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.en
dc.description.sponsorshipL.G. and X.L. were supported by the China Scholarship Council.en
dc.publisherWiley-Blackwellen
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/anie.201607646/fullen
dc.subjectalkylationen
dc.subjectalkylboron reagentsen
dc.subjectaromatic methyl ethersen
dc.subjectC−O activationen
dc.subjectnickel catalysisen
dc.titleNickel-Catalyzed Alkoxy-Alkyl Interconversion with Alkylborane Reagents through C−O Bond Activation of Aryl and Enol Ethersen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalAngewandte Chemie International Editionen
dc.contributor.institutionInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg1,52074 Aachen (Germany)en
kaust.authorRueping, Magnusen
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