Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation

Handle URI:
http://hdl.handle.net/10754/623907
Title:
Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation
Authors:
Yue, Huifeng; Guo, Lin; Lee, Shao-Chi; Liu, Xiangqian; Rueping, Magnus ( 0000-0003-4580-5227 )
Abstract:
An inexpensive nickel(II) catalyst and a hydrosilane were used for the efficient reductive defunctionalization of aryl and heteroaryl esters through a decarbonylative pathway. This versatile method could be used for the removal of ester and amide functional groups from various organic molecules. Moreover, a scale-up experiment and a synthetic application based on the use of a removable carboxylic acid directing group highlight the usefulness of this reaction.
KAUST Department:
KAUST Catalysis Center (KCC)
Citation:
Yue H, Guo L, Lee S-C, Liu X, Rueping M (2017) Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation. Angewandte Chemie International Edition 56: 3972–3976. Available: http://dx.doi.org/10.1002/anie.201612624.
Publisher:
Wiley-Blackwell
Journal:
Angewandte Chemie International Edition
Issue Date:
21-Mar-2017
DOI:
10.1002/anie.201612624; 10.1002/ange.201612624
Type:
Article
ISSN:
1433-7851
Sponsors:
H.Y. and L.G. acknowledge the China Scholarship Council. Support by King Abdullah University of Science and Technology (KAUST) is gratefully acknowledged.
Additional Links:
http://onlinelibrary.wiley.com/doi/10.1002/anie.201612624/full
Appears in Collections:
Articles; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorYue, Huifengen
dc.contributor.authorGuo, Linen
dc.contributor.authorLee, Shao-Chien
dc.contributor.authorLiu, Xiangqianen
dc.contributor.authorRueping, Magnusen
dc.date.accessioned2017-05-31T11:23:13Z-
dc.date.available2017-05-31T11:23:13Z-
dc.date.issued2017-03-21en
dc.identifier.citationYue H, Guo L, Lee S-C, Liu X, Rueping M (2017) Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation. Angewandte Chemie International Edition 56: 3972–3976. Available: http://dx.doi.org/10.1002/anie.201612624.en
dc.identifier.issn1433-7851en
dc.identifier.doi10.1002/anie.201612624en
dc.identifier.doi10.1002/ange.201612624en
dc.identifier.urihttp://hdl.handle.net/10754/623907-
dc.description.abstractAn inexpensive nickel(II) catalyst and a hydrosilane were used for the efficient reductive defunctionalization of aryl and heteroaryl esters through a decarbonylative pathway. This versatile method could be used for the removal of ester and amide functional groups from various organic molecules. Moreover, a scale-up experiment and a synthetic application based on the use of a removable carboxylic acid directing group highlight the usefulness of this reaction.en
dc.description.sponsorshipH.Y. and L.G. acknowledge the China Scholarship Council. Support by King Abdullah University of Science and Technology (KAUST) is gratefully acknowledged.en
dc.publisherWiley-Blackwellen
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/anie.201612624/fullen
dc.subjectamidesen
dc.subjectcleavage reactionsen
dc.subjectestersen
dc.subjectnickel catalysisen
dc.subjectreductionen
dc.titleSelective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activationen
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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