Rhodium‐Catalyzed Asymmetric Hydrogenation of All‐Carbon Aromatic Rings

Compared with heteroarenes, homogeneous asymmetric hydrogenation of all‐carbon aromatic rings is a longstanding challenge in organic synthesis due to the strong aromaticity and difficult enantioselective control. Herein, we report the rhodium/diphosphine‐catalyzed asymmetric hydrogenation of all‐car...

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Published inAngewandte Chemie International Edition Vol. 61; no. 34; pp. e202205623 - n/a
Main Authors Ding, Yi‐Xuan, Zhu, Zhou‐Hao, Chen, Mu‐Wang, Yu, Chang‐Bin, Zhou, Yong‐Gui
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 22.08.2022
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
All-Carbon Aromatic Rings
Aromatic compounds
Aromaticity
Asymmetric Hydrogenation
Asymmetry
Carbon
Chemistry
Chemistry, Multidisciplinary
Cyclic compounds
Desymmetrization
Enantiomers
Hydrogenation
Kinetic Resolution
Ligands
Phosphine
Phosphines
Physical Sciences
Rhodium
Science & Technology
Steric hindrance
COMPLEX
Desymmetrization
ENANTIOSELECTIVE REDUCTION
QUINOLINES
Asymmetric Hydrogenation
RUTHENIUM
HETEROAROMATIC-COMPOUNDS
All-Carbon Aromatic Rings
PHOSPHORUS LIGANDS
KETONES
Kinetic Resolution
Rhodium
ACCESS
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Abstract Compared with heteroarenes, homogeneous asymmetric hydrogenation of all‐carbon aromatic rings is a longstanding challenge in organic synthesis due to the strong aromaticity and difficult enantioselective control. Herein, we report the rhodium/diphosphine‐catalyzed asymmetric hydrogenation of all‐carbon aromatic rings, affording a series of axially chiral cyclic compounds with high enantioselectivity through desymmetrization or kinetic resolution. In addition, the central‐chiral cyclic compounds were also obtained by asymmetric hydrogenation of phenanthrenes bearing a directing group. The key to success is the introduction of chiral diphosphine ligands with steric hindrance and strong electron‐donating properties. The axially chiral monophosphine ligands could be obtained by simple conversion of the hydrogenation products bearing the phosphine atom. The first rhodium/diphosphine‐catalyzed asymmetric hydrogenation of all‐carbon aromatic rings, anthracenes and naphthalenes, was reported, affording the axially chiral biaryl compounds by desymmetrization or kinetic resolution. Meanwhile, central‐chiral cyclic compounds were also obtained by asymmetric hydrogenation of phenanthrenes. In addition, after simple conversion of the products, the axially chiral monophosphine ligands could be obtained.
AbstractList Compared with heteroarenes, homogeneous asymmetric hydrogenation of all-carbon aromatic rings is a longstanding challenge in organic synthesis due to the strong aromaticity and difficult enantioselective control. Herein, we report the rhodium/diphosphine-catalyzed asymmetric hydrogenation of all-carbon aromatic rings, affording a series of axially chiral cyclic compounds with high enantioselectivity through desymmetrization or kinetic resolution. In addition, the central-chiral cyclic compounds were also obtained by asymmetric hydrogenation of phenanthrenes bearing a directing group. The key to success is the introduction of chiral diphosphine ligands with steric hindrance and strong electron-donating properties. The axially chiral monophosphine ligands could be obtained by simple conversion of the hydrogenation products bearing the phosphine atom.
Compared with heteroarenes, homogeneous asymmetric hydrogenation of all-carbon aromatic rings is a longstanding challenge in organic synthesis due to the strong aromaticity and difficult enantioselective control. Herein, we report the rhodium/diphosphine-catalyzed asymmetric hydrogenation of all-carbon aromatic rings, affording a series of axially chiral cyclic compounds with high enantioselectivity through desymmetrization or kinetic resolution. In addition, the central-chiral cyclic compounds were also obtained by asymmetric hydrogenation of phenanthrenes bearing a directing group. The key to success is the introduction of chiral diphosphine ligands with steric hindrance and strong electron-donating properties. The axially chiral monophosphine ligands could be obtained by simple conversion of the hydrogenation products bearing the phosphine atom.Compared with heteroarenes, homogeneous asymmetric hydrogenation of all-carbon aromatic rings is a longstanding challenge in organic synthesis due to the strong aromaticity and difficult enantioselective control. Herein, we report the rhodium/diphosphine-catalyzed asymmetric hydrogenation of all-carbon aromatic rings, affording a series of axially chiral cyclic compounds with high enantioselectivity through desymmetrization or kinetic resolution. In addition, the central-chiral cyclic compounds were also obtained by asymmetric hydrogenation of phenanthrenes bearing a directing group. The key to success is the introduction of chiral diphosphine ligands with steric hindrance and strong electron-donating properties. The axially chiral monophosphine ligands could be obtained by simple conversion of the hydrogenation products bearing the phosphine atom.
Compared with heteroarenes, homogeneous asymmetric hydrogenation of all‐carbon aromatic rings is a longstanding challenge in organic synthesis due to the strong aromaticity and difficult enantioselective control. Herein, we report the rhodium/diphosphine‐catalyzed asymmetric hydrogenation of all‐carbon aromatic rings, affording a series of axially chiral cyclic compounds with high enantioselectivity through desymmetrization or kinetic resolution. In addition, the central‐chiral cyclic compounds were also obtained by asymmetric hydrogenation of phenanthrenes bearing a directing group. The key to success is the introduction of chiral diphosphine ligands with steric hindrance and strong electron‐donating properties. The axially chiral monophosphine ligands could be obtained by simple conversion of the hydrogenation products bearing the phosphine atom. The first rhodium/diphosphine‐catalyzed asymmetric hydrogenation of all‐carbon aromatic rings, anthracenes and naphthalenes, was reported, affording the axially chiral biaryl compounds by desymmetrization or kinetic resolution. Meanwhile, central‐chiral cyclic compounds were also obtained by asymmetric hydrogenation of phenanthrenes. In addition, after simple conversion of the products, the axially chiral monophosphine ligands could be obtained.
ArticleNumber 202205623
Author Chen, Mu‐Wang
Zhu, Zhou‐Hao
Yu, Chang‐Bin
Zhou, Yong‐Gui
Ding, Yi‐Xuan
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  surname: Ding
  fullname: Ding, Yi‐Xuan
  organization: University of Chinese Academy of Sciences
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  givenname: Zhou‐Hao
  surname: Zhu
  fullname: Zhu, Zhou‐Hao
  organization: University of Chinese Academy of Sciences
– sequence: 3
  givenname: Mu‐Wang
  surname: Chen
  fullname: Chen, Mu‐Wang
  organization: Chinese Academy of Sciences
– sequence: 4
  givenname: Chang‐Bin
  surname: Yu
  fullname: Yu, Chang‐Bin
  organization: Chinese Academy of Sciences
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  givenname: Yong‐Gui
  orcidid: 0000-0002-3321-5521
  surname: Zhou
  fullname: Zhou, Yong‐Gui
  email: ygzhou@dicp.ac.cn
  organization: Dalian University of Technology
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Keywords COMPLEX
Desymmetrization
ENANTIOSELECTIVE REDUCTION
QUINOLINES
Asymmetric Hydrogenation
RUTHENIUM
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All-Carbon Aromatic Rings
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Snippet Compared with heteroarenes, homogeneous asymmetric hydrogenation of all‐carbon aromatic rings is a longstanding challenge in organic synthesis due to the...
Compared with heteroarenes, homogeneous asymmetric hydrogenation of all-carbon aromatic rings is a longstanding challenge in organic synthesis due to the...
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SubjectTerms All-Carbon Aromatic Rings
Aromatic compounds
Aromaticity
Asymmetric Hydrogenation
Asymmetry
Carbon
Chemistry
Chemistry, Multidisciplinary
Cyclic compounds
Desymmetrization
Enantiomers
Hydrogenation
Kinetic Resolution
Ligands
Phosphine
Phosphines
Physical Sciences
Rhodium
Science & Technology
Steric hindrance
Title Rhodium‐Catalyzed Asymmetric Hydrogenation of All‐Carbon Aromatic Rings
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202205623
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