Divergent Synthesis of Chiral Covalent Organic Frameworks

Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the construction of natural products and potential medicines. Inspired by this approach, presented herein is a general strategy to introduce functiona...

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Published inAngewandte Chemie International Edition Vol. 58; no. 28; pp. 9443 - 9447
Main Authors Wang, Li‐Ke, Zhou, Jing‐Jing, Lan, Yu‐Bao, Ding, San‐Yuan, Yu, Wei, Wang, Wei
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 08.07.2019
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Amination
asymmetric catalysis
Catalysis
Chemistry
Chemistry, Multidisciplinary
chirality
Covalence
covalent organic frameworks
Imidazole
Natural products
Physical Sciences
Science & Technology
self-assembly
structure elucidation
Substitution reactions
Synthesis
FUNCTIONALIZATION
self-assembly
CATALYSIS
covalent organic frameworks
PHASE
chirality
ASYMMETRIC AMINATION
STABILITY
CONSTRUCTION
asymmetric catalysis
structure elucidation
CRYSTALLINE
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Abstract Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the construction of natural products and potential medicines. Inspired by this approach, presented herein is a general strategy to introduce functionality, in a divergent manner, into covalent organic frameworks (COFs). This modular protocol includes two stages of covalent assembly, through which functional COFs can be constructed by a three‐step transformation of a key platform molecule, such as 4,7‐dibromo‐2‐chloro‐1H‐benzo[d]imidazole (DBCBI). Constructed herein are four types of chiral COFs (CCOFs) from DBCBI by nucleophilic substitution, Suzuki coupling, and imine formation. The unique array of eight isoframework CCOFs allowed investigation of their catalytic performance and structure–activity relationship in an asymmetric amination reaction. COF it up: A divergent strategy has been used to construct a combinatorial library of functional covalent organic frameworks (COFs) from a platform molecule. An array of eight isoframework chiral COFs allowed investigation of their catalytic performance and structure–activity relationship in an asymmetric amination reaction.
AbstractList Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the construction of natural products and potential medicines. Inspired by this approach, presented herein is a general strategy to introduce functionality, in a divergent manner, into covalent organic frameworks (COFs). This modular protocol includes two stages of covalent assembly, through which functional COFs can be constructed by a three-step transformation of a key platform molecule, such as 4,7-dibromo-2-chloro-1H-benzo[d]imidazole (DBCBI). Constructed herein are four types of chiral COFs (CCOFs) from DBCBI by nucleophilic substitution, Suzuki coupling, and imine formation. The unique array of eight isoframework CCOFs allowed investigation of their catalytic performance and structure-activity relationship in an asymmetric amination reaction.Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the construction of natural products and potential medicines. Inspired by this approach, presented herein is a general strategy to introduce functionality, in a divergent manner, into covalent organic frameworks (COFs). This modular protocol includes two stages of covalent assembly, through which functional COFs can be constructed by a three-step transformation of a key platform molecule, such as 4,7-dibromo-2-chloro-1H-benzo[d]imidazole (DBCBI). Constructed herein are four types of chiral COFs (CCOFs) from DBCBI by nucleophilic substitution, Suzuki coupling, and imine formation. The unique array of eight isoframework CCOFs allowed investigation of their catalytic performance and structure-activity relationship in an asymmetric amination reaction.
Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the construction of natural products and potential medicines. Inspired by this approach, presented herein is a general strategy to introduce functionality, in a divergent manner, into covalent organic frameworks (COFs). This modular protocol includes two stages of covalent assembly, through which functional COFs can be constructed by a three‐step transformation of a key platform molecule, such as 4,7‐dibromo‐2‐chloro‐1H‐benzo[d]imidazole (DBCBI). Constructed herein are four types of chiral COFs (CCOFs) from DBCBI by nucleophilic substitution, Suzuki coupling, and imine formation. The unique array of eight isoframework CCOFs allowed investigation of their catalytic performance and structure–activity relationship in an asymmetric amination reaction. COF it up: A divergent strategy has been used to construct a combinatorial library of functional covalent organic frameworks (COFs) from a platform molecule. An array of eight isoframework chiral COFs allowed investigation of their catalytic performance and structure–activity relationship in an asymmetric amination reaction.
Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the construction of natural products and potential medicines. Inspired by this approach, presented herein is a general strategy to introduce functionality, in a divergent manner, into covalent organic frameworks (COFs). This modular protocol includes two stages of covalent assembly, through which functional COFs can be constructed by a three-step transformation of a key platform molecule, such as 4,7-dibromo-2-chloro-1H-benzo[d]imidazole (DBCBI). Constructed herein are four types of chiral COFs (CCOFs) from DBCBI by nucleophilic substitution, Suzuki coupling, and imine formation. The unique array of eight isoframework CCOFs allowed investigation of their catalytic performance and structure-activity relationship in an asymmetric amination reaction.
Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the construction of natural products and potential medicines. Inspired by this approach, presented herein is a general strategy to introduce functionality, in a divergent manner, into covalent organic frameworks (COFs). This modular protocol includes two stages of covalent assembly, through which functional COFs can be constructed by a three‐step transformation of a key platform molecule, such as 4,7‐dibromo‐2‐chloro‐1 H ‐benzo[ d ]imidazole (DBCBI). Constructed herein are four types of chiral COFs (CCOFs) from DBCBI by nucleophilic substitution, Suzuki coupling, and imine formation. The unique array of eight isoframework CCOFs allowed investigation of their catalytic performance and structure–activity relationship in an asymmetric amination reaction.
Author Zhou, Jing‐Jing
Wang, Wei
Lan, Yu‐Bao
Yu, Wei
Wang, Li‐Ke
Ding, San‐Yuan
Author_xml – sequence: 1
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  surname: Wang
  fullname: Wang, Li‐Ke
  organization: Lanzhou University
– sequence: 2
  givenname: Jing‐Jing
  surname: Zhou
  fullname: Zhou, Jing‐Jing
  organization: Lanzhou University
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  givenname: Yu‐Bao
  surname: Lan
  fullname: Lan, Yu‐Bao
  organization: Lanzhou University
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  givenname: San‐Yuan
  orcidid: 0000-0003-2160-4092
  surname: Ding
  fullname: Ding, San‐Yuan
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  givenname: Wei
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  surname: Yu
  fullname: Yu, Wei
  organization: Lanzhou University
– sequence: 6
  givenname: Wei
  orcidid: 0000-0002-9263-7927
  surname: Wang
  fullname: Wang, Wei
  email: wang_wei@lzu.edu.cn
  organization: Lanzhou University
BackLink https://www.ncbi.nlm.nih.gov/pubmed/31090130$$D View this record in MEDLINE/PubMed
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Issue 28
Keywords FUNCTIONALIZATION
self-assembly
CATALYSIS
covalent organic frameworks
PHASE
chirality
ASYMMETRIC AMINATION
STABILITY
CONSTRUCTION
asymmetric catalysis
structure elucidation
CRYSTALLINE
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Snippet Featuring the simultaneous generation of a library of compounds from a certain intermediate, divergent synthesis has found increasing applications in the...
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SubjectTerms Amination
asymmetric catalysis
Catalysis
Chemistry
Chemistry, Multidisciplinary
chirality
Covalence
covalent organic frameworks
Imidazole
Natural products
Physical Sciences
Science & Technology
self-assembly
structure elucidation
Substitution reactions
Synthesis
Title Divergent Synthesis of Chiral Covalent Organic Frameworks
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201903534
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https://www.ncbi.nlm.nih.gov/pubmed/31090130
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