TEMPO Mediated Cyclopropanols Ring Opening C−N Cross‐Coupling with Nitrogen Nucleophiles

A feasible and umpolung strategy for the synthesis of structurally diverse β‐amino ketones has been achieved through TEMPO mediated C−N coupling of cyclopropanols with nitrogen nucleophiles. Mechanism studies indicated that in situ generated enones derived from cyclopropanols are the key intermediat...

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Published inAdvanced synthesis & catalysis Vol. 365; no. 10; pp. 1678 - 1684
Main Authors Zhan, Jun‐Long, Zhu, Lin, Ren, Wei, Wang, Bing‐Jie, Zhao, Xin‐Ming, Zhang, Xin‐Ru, Zhang, Xin‐Yu, Xie, Yao‐Qiang
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 23.05.2023
Wiley Subscription Services, Inc
Subjects
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
Cross coupling
cyclopropanols
C−N coupling
Ketones
Nitrogen
Nucleophiles
Physical Sciences
Reagents
Ring opening
Science & Technology
Substrates
TEMPO
β-amino ketones
HYDRAZONES
ALKYL
ANNULATION
CLEAVAGE
SATURATED KETONES
FUNCTIONALIZATION
ALKENES
AMINATION
C-N coupling
AEROBIC OXIDATION
TEMPO
cyclopropanols
EFFICIENT
beta-amino ketones
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Abstract A feasible and umpolung strategy for the synthesis of structurally diverse β‐amino ketones has been achieved through TEMPO mediated C−N coupling of cyclopropanols with nitrogen nucleophiles. Mechanism studies indicated that in situ generated enones derived from cyclopropanols are the key intermediates and TEMPO play multiple roles, including radical initiator, trapping reagent, a porter of β‐hydrogen and an in situ base. This protocol features broad substrate scope, good scalability and good to excellent yields and provides an alternative and complementary approach to the synthesis of structurally important β‐amino ketone scaffolds under metal and additive‐free conditions.
AbstractList A feasible and umpolung strategy for the synthesis of structurally diverse β‐amino ketones has been achieved through TEMPO mediated C−N coupling of cyclopropanols with nitrogen nucleophiles. Mechanism studies indicated that in situ generated enones derived from cyclopropanols are the key intermediates and TEMPO play multiple roles, including radical initiator, trapping reagent, a porter of β‐hydrogen and an in situ base. This protocol features broad substrate scope, good scalability and good to excellent yields and provides an alternative and complementary approach to the synthesis of structurally important β‐amino ketone scaffolds under metal and additive‐free conditions.
A feasible and umpolung strategy for the synthesis of structurally diverse β ‐amino ketones has been achieved through TEMPO mediated C−N coupling of cyclopropanols with nitrogen nucleophiles. Mechanism studies indicated that in situ generated enones derived from cyclopropanols are the key intermediates and TEMPO play multiple roles, including radical initiator, trapping reagent, a porter of β ‐hydrogen and an in situ base. This protocol features broad substrate scope, good scalability and good to excellent yields and provides an alternative and complementary approach to the synthesis of structurally important β ‐amino ketone scaffolds under metal and additive‐free conditions. magnified image
A feasible and umpolung strategy for the synthesis of structurally diverse beta-amino ketones has been achieved through TEMPO mediated C N coupling of cyclopropanols with nitrogen nucleophiles. Mechanism studies indicated that in situ generated enones derived from cyclopropanols are the key intermediates and TEMPO play multiple roles, including radical initiator, trapping reagent, a porter of beta-hydrogen and an in situ base. This protocol features broad substrate scope, good scalability and good to excellent yields and provides an alternative and complementary approach to the synthesis of structurally important beta-amino ketone scaffolds under metal and additive-free conditions.
Author Zhu, Lin
Zhao, Xin‐Ming
Zhang, Xin‐Ru
Wang, Bing‐Jie
Xie, Yao‐Qiang
Zhan, Jun‐Long
Ren, Wei
Zhang, Xin‐Yu
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  surname: Zhan
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  organization: Lanzhou University
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  givenname: Lin
  surname: Zhu
  fullname: Zhu, Lin
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  surname: Xie
  fullname: Xie, Yao‐Qiang
  organization: Anyang Normal University
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Keywords HYDRAZONES
ALKYL
ANNULATION
CLEAVAGE
SATURATED KETONES
FUNCTIONALIZATION
ALKENES
AMINATION
C-N coupling
AEROBIC OXIDATION
TEMPO
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Snippet A feasible and umpolung strategy for the synthesis of structurally diverse β‐amino ketones has been achieved through TEMPO mediated C−N coupling of...
A feasible and umpolung strategy for the synthesis of structurally diverse β ‐amino ketones has been achieved through TEMPO mediated C−N coupling of...
A feasible and umpolung strategy for the synthesis of structurally diverse beta-amino ketones has been achieved through TEMPO mediated C N coupling of...
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SubjectTerms Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Organic
Cross coupling
cyclopropanols
C−N coupling
Ketones
Nitrogen
Nucleophiles
Physical Sciences
Reagents
Ring opening
Science & Technology
Substrates
TEMPO
β-amino ketones
Title TEMPO Mediated Cyclopropanols Ring Opening C−N Cross‐Coupling with Nitrogen Nucleophiles
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fadsc.202300108
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