Copper‐Catalyzed Intermolecular Enantioselective Radical Oxidative C(sp3)−H/C(sp)−H Cross‐Coupling with Rationally Designed Oxazoline‐Derived N,N,P(O)‐Ligands

The intermolecular asymmetric radical oxidative C(sp3)−C(sp) cross‐coupling of C(sp3)−H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp3)−C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper‐catalyzed asym...

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Published inAngewandte Chemie International Edition Vol. 60; no. 51; pp. 26710 - 26717
Main Authors Liu, Lin, Guo, Kai‐Xin, Tian, Yu, Yang, Chang‐Jiang, Gu, Qiang‐Shuai, Li, Zhong‐Liang, Ye, Liu, Liu, Xin‐Yuan
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 13.12.2021
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkynes
alkynylation
anionic N,N,P(O)-ligands
Asymmetry
Chemical bonds
Chemistry
Chemistry, Multidisciplinary
Copper
copper catalysis
Cross coupling
Enantiomers
Ligands
oxidative cross-coupling
Physical Sciences
radical asymmetric chemistry
Radicals
Science & Technology
Selectivity
SUBSTITUTION
TETRAHYDROISOQUINOLINES
anionic N
ARYLATION
ALLYLIC ALKYLATION
alkynylation
H BOND FUNCTIONALIZATION
N
P(O)-ligands
copper catalysis
IODIDES
oxidative cross-coupling
LIGANDS
radical asymmetric chemistry
ARYL
anionic N,N,P(O)-ligands
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Abstract The intermolecular asymmetric radical oxidative C(sp3)−C(sp) cross‐coupling of C(sp3)−H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp3)−C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper‐catalyzed asymmetric C(sp3)−C(sp) cross‐coupling of (hetero)benzylic and (cyclic)allylic C−H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline‐derived N,N,P(O)‐ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom ion (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4‐enynes, high site‐selectivity among similar C(sp3)−H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive. Chiral benzylic alkynes and 1,4‐enynes can be obtained in a straightforward approach from commercially available terminal alkynes and a diverse range of compounds containing benzylic and allylic C−H bonds by using the title reaction. The success of this approach lies in newly designed anionic N,N,P(O)‐ligands bearing a stable chiral oxazoline and a pentavalent phosphine oxide that are generated in situ.
AbstractList The intermolecular asymmetric radical oxidative C(sp(3))-C(sp) cross-coupling of C(sp(3))-H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp(3))-C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper-catalyzed asymmetric C(sp(3))-C(sp) cross-coupling of (hetero)benzylic and (cyclic)allylic C-H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline-derived N,N,P(O)-ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom abstraction (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4-enynes, high site-selectivity among similar C(sp(3))-H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive.
The intermolecular asymmetric radical oxidative C(sp )-C(sp) cross-coupling of C(sp )-H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp )-C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper-catalyzed asymmetric C(sp )-C(sp) cross-coupling of (hetero)benzylic and (cyclic)allylic C-H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline-derived N,N,P(O)-ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom abstraction (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4-enynes, high site-selectivity among similar C(sp )-H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive.
The intermolecular asymmetric radical oxidative C(sp3 )-C(sp) cross-coupling of C(sp3 )-H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp3 )-C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper-catalyzed asymmetric C(sp3 )-C(sp) cross-coupling of (hetero)benzylic and (cyclic)allylic C-H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline-derived N,N,P(O)-ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom abstraction (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4-enynes, high site-selectivity among similar C(sp3 )-H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive.The intermolecular asymmetric radical oxidative C(sp3 )-C(sp) cross-coupling of C(sp3 )-H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp3 )-C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper-catalyzed asymmetric C(sp3 )-C(sp) cross-coupling of (hetero)benzylic and (cyclic)allylic C-H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline-derived N,N,P(O)-ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom abstraction (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4-enynes, high site-selectivity among similar C(sp3 )-H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive.
The intermolecular asymmetric radical oxidative C(sp3)−C(sp) cross‐coupling of C(sp3)−H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp3)−C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper‐catalyzed asymmetric C(sp3)−C(sp) cross‐coupling of (hetero)benzylic and (cyclic)allylic C−H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline‐derived N,N,P(O)‐ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom abstraction (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4‐enynes, high site‐selectivity among similar C(sp3)−H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive.
The intermolecular asymmetric radical oxidative C(sp3)−C(sp) cross‐coupling of C(sp3)−H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp3)−C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper‐catalyzed asymmetric C(sp3)−C(sp) cross‐coupling of (hetero)benzylic and (cyclic)allylic C−H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline‐derived N,N,P(O)‐ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom ion (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4‐enynes, high site‐selectivity among similar C(sp3)−H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive. Chiral benzylic alkynes and 1,4‐enynes can be obtained in a straightforward approach from commercially available terminal alkynes and a diverse range of compounds containing benzylic and allylic C−H bonds by using the title reaction. The success of this approach lies in newly designed anionic N,N,P(O)‐ligands bearing a stable chiral oxazoline and a pentavalent phosphine oxide that are generated in situ.
The intermolecular asymmetric radical oxidative C(sp 3 )−C(sp) cross‐coupling of C(sp 3 )−H bonds with readily available terminal alkynes is a promising method to forge chiral C(sp 3 )−C(sp) bonds because of the high atom and step economy, but remains underexplored. Here, we report a copper‐catalyzed asymmetric C(sp 3 )−C(sp) cross‐coupling of (hetero)benzylic and (cyclic)allylic C−H bonds with terminal alkynes that occurs with high to excellent enantioselectivity. Critical to the success is the rational design of chiral oxazoline‐derived N,N,P(O)‐ligands that not only tolerate the strong oxidative conditions which are requisite for intermolecular hydrogen atom abstraction (HAA) processes but also induce the challenging enantiocontrol. Direct access to a range of synthetically useful chiral benzylic alkynes and 1,4‐enynes, high site‐selectivity among similar C(sp 3 )−H bonds, and facile synthesis of enantioenriched medicinally relevant compounds make this approach very attractive.
Author Yang, Chang‐Jiang
Li, Zhong‐Liang
Liu, Xin‐Yuan
Ye, Liu
Gu, Qiang‐Shuai
Guo, Kai‐Xin
Tian, Yu
Liu, Lin
Author_xml – sequence: 1
  givenname: Lin
  surname: Liu
  fullname: Liu, Lin
  organization: Southern University of Science and Technology
– sequence: 2
  givenname: Kai‐Xin
  surname: Guo
  fullname: Guo, Kai‐Xin
  organization: Southern University of Science and Technology
– sequence: 3
  givenname: Yu
  surname: Tian
  fullname: Tian, Yu
  organization: Southern University of Science and Technology
– sequence: 4
  givenname: Chang‐Jiang
  surname: Yang
  fullname: Yang, Chang‐Jiang
  organization: Southern University of Science and Technology
– sequence: 5
  givenname: Qiang‐Shuai
  surname: Gu
  fullname: Gu, Qiang‐Shuai
  organization: Southern University of Science and Technology
– sequence: 6
  givenname: Zhong‐Liang
  surname: Li
  fullname: Li, Zhong‐Liang
  organization: Southern University of Science and Technology
– sequence: 7
  givenname: Liu
  surname: Ye
  fullname: Ye, Liu
  email: yel@sustech.edu.cn
  organization: Southern University of Science and Technology
– sequence: 8
  givenname: Xin‐Yuan
  orcidid: 0000-0002-6978-6465
  surname: Liu
  fullname: Liu, Xin‐Yuan
  email: liuxy3@sustech.edu.cn
  organization: Southern University of Science and Technology
BackLink https://www.ncbi.nlm.nih.gov/pubmed/34606167$$D View this record in MEDLINE/PubMed
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IEDL.DBID DR2
ISICitedReferencesCount 56
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ISSN 1433-7851
1521-3773
IngestDate Fri Jul 11 16:16:13 EDT 2025
Fri Jul 25 10:34:46 EDT 2025
Thu Apr 03 06:58:10 EDT 2025
Fri Aug 22 19:06:37 EDT 2025
Mon Jul 21 06:54:24 EDT 2025
Thu Apr 24 22:56:43 EDT 2025
Tue Jul 01 01:18:09 EDT 2025
Wed Jan 22 16:28:15 EST 2025
IsPeerReviewed true
IsScholarly true
Issue 51
Keywords SUBSTITUTION
TETRAHYDROISOQUINOLINES
anionic N
ARYLATION
ALLYLIC ALKYLATION
alkynylation
H BOND FUNCTIONALIZATION
N
P(O)-ligands
copper catalysis
IODIDES
oxidative cross-coupling
LIGANDS
radical asymmetric chemistry
ARYL
anionic N,N,P(O)-ligands
Language English
License 2021 Wiley-VCH GmbH.
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MergedId FETCHMERGED-LOGICAL-c3733-7d24ec13f696a97fc7029128687280b7d2dc819f160491bddb3988c5339945c23
Notes Dedicated to the 100th anniversary of Chemistry at Nankai University
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content type line 14
content type line 23
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0009-0004-9601-2563
0000-0003-3405-1546
PMID 34606167
PQID 2606919284
PQPubID 946352
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PublicationTitle Angewandte Chemie International Edition
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SSID ssj0028806
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Snippet The intermolecular asymmetric radical oxidative C(sp3)−C(sp) cross‐coupling of C(sp3)−H bonds with readily available terminal alkynes is a promising method to...
The intermolecular asymmetric radical oxidative C(sp 3 )−C(sp) cross‐coupling of C(sp 3 )−H bonds with readily available terminal alkynes is a promising method...
The intermolecular asymmetric radical oxidative C(sp(3))-C(sp) cross-coupling of C(sp(3))-H bonds with readily available terminal alkynes is a promising method...
The intermolecular asymmetric radical oxidative C(sp )-C(sp) cross-coupling of C(sp )-H bonds with readily available terminal alkynes is a promising method to...
The intermolecular asymmetric radical oxidative C(sp3 )-C(sp) cross-coupling of C(sp3 )-H bonds with readily available terminal alkynes is a promising method...
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SubjectTerms Alkynes
alkynylation
anionic N,N,P(O)-ligands
Asymmetry
Chemical bonds
Chemistry
Chemistry, Multidisciplinary
Copper
copper catalysis
Cross coupling
Enantiomers
Ligands
oxidative cross-coupling
Physical Sciences
radical asymmetric chemistry
Radicals
Science & Technology
Selectivity
Title Copper‐Catalyzed Intermolecular Enantioselective Radical Oxidative C(sp3)−H/C(sp)−H Cross‐Coupling with Rationally Designed Oxazoline‐Derived N,N,P(O)‐Ligands
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202110233
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https://www.ncbi.nlm.nih.gov/pubmed/34606167
https://www.proquest.com/docview/2606919284
https://www.proquest.com/docview/2579086001
Volume 60
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