Palladium‐Catalyzed Formal Cross‐Coupling of Diaryl Ethers with Amines: Slicing the 4‐O‐5 Linkage in Lignin Models

Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value‐added platform chemicals instead of using fossil‐based re...

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Published inAngewandte Chemie International Edition Vol. 57; no. 14; pp. 3752 - 3757
Main Authors Zeng, Huiying, Cao, Dawei, Qiu, Zihang, Li, Chao‐Jun
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 26.03.2018
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Amines
Aromatic compounds
Chemical bonds
Chemistry
Chemistry, Multidisciplinary
Coupling
cross-coupling
Cyclohexane
Cyclohexanol
Cyclohexanone
C−O bond cleavage
Diaryl ethers
Energy of dissociation
Ethers
Free energy
Heat of formation
Lignin
Organic matter
Palladium
Phenols
Physical Sciences
Polymers
Science & Technology
Slicing
Sustainable production
HYDROGENOLYSIS
O BOND-CLEAVAGE
CONVERSION
C-O bond cleavage
amines
DEPOLYMERIZATION
lignin
SELECTIVE REDUCTIVE CLEAVAGE
ARYL ETHERS
PHENOLS
BIO-OIL
BIOMASS
diaryl ethers
cross-coupling
HYDROLYTIC CLEAVAGE
C−O bond cleavage
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Abstract Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value‐added platform chemicals instead of using fossil‐based resources. Lignins are aromatic polymers linked by three types of ether bonds (α‐O‐4, β‐O‐4, and 4‐O‐5 linkages) and other C−C bonds. Among the ether bonds, the bond dissociation energy of the 4‐O‐5 linkage is the highest and the most challenging to cleave. To date, 4‐O‐5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross‐coupling of diaryl ether 4‐O‐5 linkage models with amines is reported, in which dual C(Ar)−O bond cleavages form valuable nitrogen‐containing derivatives. From waste to value: A strategy for converting renewable lignin biomass into value‐added nitrogen‐containing chemicals is reported. Model compounds of lignin containing a 4‐O‐5 linker were cross‐coupled with amines by dual C(Ar)−O bond cleavages to generate valuable nitrogen‐containing derivatives.
AbstractList Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value-added platform chemicals instead of using fossil-based resources. Lignins are aromatic polymers linked by three types of ether bonds (α-O-4, β-O-4, and 4-O-5 linkages) and other C-C bonds. Among the ether bonds, the bond dissociation energy of the 4-O-5 linkage is the highest and the most challenging to cleave. To date, 4-O-5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross-coupling of diaryl ether 4-O-5 linkage models with amines is reported, in which dual C(Ar)-O bond cleavages form valuable nitrogen-containing derivatives.
Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value-added platform chemicals instead of using fossil-based resources. Lignins are aromatic polymers linked by three types of ether bonds (α-O-4, β-O-4, and 4-O-5 linkages) and other C-C bonds. Among the ether bonds, the bond dissociation energy of the 4-O-5 linkage is the highest and the most challenging to cleave. To date, 4-O-5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross-coupling of diaryl ether 4-O-5 linkage models with amines is reported, in which dual C(Ar)-O bond cleavages form valuable nitrogen-containing derivatives.Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value-added platform chemicals instead of using fossil-based resources. Lignins are aromatic polymers linked by three types of ether bonds (α-O-4, β-O-4, and 4-O-5 linkages) and other C-C bonds. Among the ether bonds, the bond dissociation energy of the 4-O-5 linkage is the highest and the most challenging to cleave. To date, 4-O-5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross-coupling of diaryl ether 4-O-5 linkage models with amines is reported, in which dual C(Ar)-O bond cleavages form valuable nitrogen-containing derivatives.
Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value‐added platform chemicals instead of using fossil‐based resources. Lignins are aromatic polymers linked by three types of ether bonds (α‐O‐4, β‐O‐4, and 4‐O‐5 linkages) and other C−C bonds. Among the ether bonds, the bond dissociation energy of the 4‐O‐5 linkage is the highest and the most challenging to cleave. To date, 4‐O‐5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross‐coupling of diaryl ether 4‐O‐5 linkage models with amines is reported, in which dual C(Ar)−O bond cleavages form valuable nitrogen‐containing derivatives. From waste to value: A strategy for converting renewable lignin biomass into value‐added nitrogen‐containing chemicals is reported. Model compounds of lignin containing a 4‐O‐5 linker were cross‐coupled with amines by dual C(Ar)−O bond cleavages to generate valuable nitrogen‐containing derivatives.
Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value‐added platform chemicals instead of using fossil‐based resources. Lignins are aromatic polymers linked by three types of ether bonds (α‐O‐4, β‐O‐4, and 4‐O‐5 linkages) and other C−C bonds. Among the ether bonds, the bond dissociation energy of the 4‐O‐5 linkage is the highest and the most challenging to cleave. To date, 4‐O‐5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross‐coupling of diaryl ether 4‐O‐5 linkage models with amines is reported, in which dual C(Ar)−O bond cleavages form valuable nitrogen‐containing derivatives.
Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable production of aromatic compounds, it is highly desirable to convert lignin into value-added platform chemicals instead of using fossil-based resources. Lignins are aromatic polymers linked by three types of ether bonds (-O-4, -O-4, and 4-O-5 linkages) and other C-C bonds. Among the ether bonds, the bond dissociation energy of the 4-O-5 linkage is the highest and the most challenging to cleave. To date, 4-O-5 ether linkage model compounds have been cleaved to obtain phenol, cyclohexane, cyclohexanone, and cyclohexanol. The first example of direct formal cross-coupling of diaryl ether 4-O-5 linkage models with amines is reported, in which dual C(Ar)-O bond cleavages form valuable nitrogen-containing derivatives.
Author Qiu, Zihang
Li, Chao‐Jun
Cao, Dawei
Zeng, Huiying
Author_xml – sequence: 1
  givenname: Huiying
  orcidid: 0000-0002-2535-111X
  surname: Zeng
  fullname: Zeng, Huiying
  email: zenghy@lzu.edu.cn
  organization: Lanzhou University
– sequence: 2
  givenname: Dawei
  surname: Cao
  fullname: Cao, Dawei
  organization: Lanzhou University
– sequence: 3
  givenname: Zihang
  surname: Qiu
  fullname: Qiu, Zihang
  organization: McGill University
– sequence: 4
  givenname: Chao‐Jun
  orcidid: 0000-0002-3859-8824
  surname: Li
  fullname: Li, Chao‐Jun
  email: cj.li@mcgill.ca
  organization: McGill University
BackLink https://www.ncbi.nlm.nih.gov/pubmed/29384588$$D View this record in MEDLINE/PubMed
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Issue 14
Keywords HYDROGENOLYSIS
O BOND-CLEAVAGE
CONVERSION
C-O bond cleavage
amines
DEPOLYMERIZATION
lignin
SELECTIVE REDUCTIVE CLEAVAGE
ARYL ETHERS
PHENOLS
BIO-OIL
BIOMASS
diaryl ethers
cross-coupling
HYDROLYTIC CLEAVAGE
C−O bond cleavage
Language English
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2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Snippet Lignin is the second most abundant organic matter on Earth, and is an underutilized renewable source for valuable aromatic chemicals. For future sustainable...
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SubjectTerms Amines
Aromatic compounds
Chemical bonds
Chemistry
Chemistry, Multidisciplinary
Coupling
cross-coupling
Cyclohexane
Cyclohexanol
Cyclohexanone
C−O bond cleavage
Diaryl ethers
Energy of dissociation
Ethers
Free energy
Heat of formation
Lignin
Organic matter
Palladium
Phenols
Physical Sciences
Polymers
Science & Technology
Slicing
Sustainable production
Title Palladium‐Catalyzed Formal Cross‐Coupling of Diaryl Ethers with Amines: Slicing the 4‐O‐5 Linkage in Lignin Models
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https://www.proquest.com/docview/2017711342
https://www.proquest.com/docview/1993010635
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