Intermolecular Enantioselective Benzylic C(sp3)−H Amination by Cationic Copper Catalysis

Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp3)−H functionalization by hydrogen‐atom transfer has emerged as a straightforward, powerful tool for the synthesis of chiral amines, but methods for intermolecular enantios...

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Published inAngewandte Chemie International Edition Vol. 62; no. 24; pp. e202304427 - n/a
Main Authors Dai, Ling, Chen, Ying‐Ying, Xiao, Li‐Jun, Zhou, Qi‐Lin
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 12.06.2023
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Amides
Amination
Amines
Asymmetric Catalysis
Benzylamines
Catalysis
Cations
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Copper
C−H Amination
Enantiomers
Functional groups
Hydrogen
Oxidants
Oxidizing agents
Physical Sciences
Radicals
Science & Technology
Substrates
Asymmetric Catalysis
ASYMMETRIC-SYNTHESIS
C-H Amination
HYDROCARBONS
BONDS
Benzylamines
AMIDATION
ALLYLIC OXIDATION
OLEFINS
NITRENE TRANSFER-REACTIONS
Copper
Radicals
C−H Amination
Online AccessGet full text
ISSN1433-7851
1521-3773
1521-3773
DOI10.1002/anie.202304427

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Abstract Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp3)−H functionalization by hydrogen‐atom transfer has emerged as a straightforward, powerful tool for the synthesis of chiral amines, but methods for intermolecular enantioselective C(sp3)−H amination remain elusive. Herein, we report a cationic copper catalytic system for intermolecular enantioselective benzylic C(sp3)−H amination with peroxide as an oxidant. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and broad substrate scope. More importantly, it can be used to synthesize bioactive molecules, including chiral drugs. Preliminary mechanistic studies indicate that the amination reaction involves benzylic radicals generated by hydrogen‐atom transfer. A highly enantioselective intermolecular benzylic C(sp3)−H bond amination by using a chiral cationic copper catalyst and oxidant di‐tert‐butyl peroxide is reported. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and a broad substrate scope.
AbstractList Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp 3 )−H functionalization by hydrogen‐atom transfer has emerged as a straightforward, powerful tool for the synthesis of chiral amines, but methods for intermolecular enantioselective C(sp 3 )−H amination remain elusive. Herein, we report a cationic copper catalytic system for intermolecular enantioselective benzylic C(sp 3 )−H amination with peroxide as an oxidant. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and broad substrate scope. More importantly, it can be used to synthesize bioactive molecules, including chiral drugs. Preliminary mechanistic studies indicate that the amination reaction involves benzylic radicals generated by hydrogen‐atom transfer.
Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp3)−H functionalization by hydrogen‐atom transfer has emerged as a straightforward, powerful tool for the synthesis of chiral amines, but methods for intermolecular enantioselective C(sp3)−H amination remain elusive. Herein, we report a cationic copper catalytic system for intermolecular enantioselective benzylic C(sp3)−H amination with peroxide as an oxidant. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and broad substrate scope. More importantly, it can be used to synthesize bioactive molecules, including chiral drugs. Preliminary mechanistic studies indicate that the amination reaction involves benzylic radicals generated by hydrogen‐atom transfer. A highly enantioselective intermolecular benzylic C(sp3)−H bond amination by using a chiral cationic copper catalyst and oxidant di‐tert‐butyl peroxide is reported. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and a broad substrate scope.
Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp(3))-H functionalization by hydrogen-atom transfer has emerged as a straightforward, powerful tool for the synthesis of chiral amines, but methods for intermolecular enantioselective C(sp(3))-H amination remain elusive. Herein, we report a cationic copper catalytic system for intermolecular enantioselective benzylic C(sp(3))-H amination with peroxide as an oxidant. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and broad substrate scope. More importantly, it can be used to synthesize bioactive molecules, including chiral drugs. Preliminary mechanistic studies indicate that the amination reaction involves benzylic radicals generated by hydrogen-atom transfer.
Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp3 )-H functionalization by hydrogen-atom transfer has emerged as a straightforward, powerful tool for the synthesis of chiral amines, but methods for intermolecular enantioselective C(sp3 )-H amination remain elusive. Herein, we report a cationic copper catalytic system for intermolecular enantioselective benzylic C(sp3 )-H amination with peroxide as an oxidant. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and broad substrate scope. More importantly, it can be used to synthesize bioactive molecules, including chiral drugs. Preliminary mechanistic studies indicate that the amination reaction involves benzylic radicals generated by hydrogen-atom transfer.Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp3 )-H functionalization by hydrogen-atom transfer has emerged as a straightforward, powerful tool for the synthesis of chiral amines, but methods for intermolecular enantioselective C(sp3 )-H amination remain elusive. Herein, we report a cationic copper catalytic system for intermolecular enantioselective benzylic C(sp3 )-H amination with peroxide as an oxidant. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and broad substrate scope. More importantly, it can be used to synthesize bioactive molecules, including chiral drugs. Preliminary mechanistic studies indicate that the amination reaction involves benzylic radicals generated by hydrogen-atom transfer.
Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp3)−H functionalization by hydrogen‐atom transfer has emerged as a straightforward, powerful tool for the synthesis of chiral amines, but methods for intermolecular enantioselective C(sp3)−H amination remain elusive. Herein, we report a cationic copper catalytic system for intermolecular enantioselective benzylic C(sp3)−H amination with peroxide as an oxidant. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and broad substrate scope. More importantly, it can be used to synthesize bioactive molecules, including chiral drugs. Preliminary mechanistic studies indicate that the amination reaction involves benzylic radicals generated by hydrogen‐atom transfer.
Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp )-H functionalization by hydrogen-atom transfer has emerged as a straightforward, powerful tool for the synthesis of chiral amines, but methods for intermolecular enantioselective C(sp )-H amination remain elusive. Herein, we report a cationic copper catalytic system for intermolecular enantioselective benzylic C(sp )-H amination with peroxide as an oxidant. This mild, straightforward method can be used to transform an array of feedstock alkylarenes and amides into chiral amines with high enantioselectivities, and it has good functional group tolerance and broad substrate scope. More importantly, it can be used to synthesize bioactive molecules, including chiral drugs. Preliminary mechanistic studies indicate that the amination reaction involves benzylic radicals generated by hydrogen-atom transfer.
Author Chen, Ying‐Ying
Zhou, Qi‐Lin
Dai, Ling
Xiao, Li‐Jun
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  fullname: Chen, Ying‐Ying
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  givenname: Li‐Jun
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  surname: Zhou
  fullname: Zhou, Qi‐Lin
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Issue 24
Keywords Asymmetric Catalysis
ASYMMETRIC-SYNTHESIS
C-H Amination
HYDROCARBONS
BONDS
Benzylamines
AMIDATION
ALLYLIC OXIDATION
OLEFINS
NITRENE TRANSFER-REACTIONS
Copper
Radicals
C−H Amination
Language English
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A previous version of this manuscript has been deposited on a preprint server
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Snippet Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp3)−H functionalization by...
Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp 3 )−H functionalization by...
Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp(3))-H functionalization by...
Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp )-H functionalization by...
Chiral benzylic amines are privileged motifs in pharmacologically active molecules. Intramolecular enantioselective radical C(sp3 )-H functionalization by...
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SubjectTerms Amides
Amination
Amines
Asymmetric Catalysis
Benzylamines
Catalysis
Cations
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Copper
C−H Amination
Enantiomers
Functional groups
Hydrogen
Oxidants
Oxidizing agents
Physical Sciences
Radicals
Science & Technology
Substrates
Title Intermolecular Enantioselective Benzylic C(sp3)−H Amination by Cationic Copper Catalysis
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202304427
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https://www.ncbi.nlm.nih.gov/pubmed/37057709
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https://www.proquest.com/docview/2801977582
Volume 62
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