Selective E to Z isomerization of 1,3-Dienes Enabled by A Dinuclear Mechanism

The E / Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily addressable by thermal Z to E geometric isomerization through equilibrium, it has remained difficult to undergo thermal geometric isomerization to the re...

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Published inNature communications Vol. 12; no. 1; p. 1473
Main Authors Kudo, Eiji, Sasaki, Kota, Kawamata, Shiori, Yamamoto, Koji, Murahashi, Tetsuro
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 05.03.2021
Nature Publishing Group
Nature Portfolio
Subjects
119/118
140/131
140/58
639/638/263/406/910
639/638/403/935
639/638/549/933
Carbon
Chemical energy
Dienes
Energy
Equilibrium
Humanities and Social Sciences
Injection
Isomerization
Isomers
multidisciplinary
Science
Science (multidisciplinary)
Trapping
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Abstract The E / Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily addressable by thermal Z to E geometric isomerization through equilibrium, it has remained difficult to undergo thermal geometric isomerization to the reverse E to Z direction in a selective manner, because it requires kinetic trapping of Z -isomer with injection of chemical energy. Here we report that a dinuclear Pd I −Pd I complex mediates selective isomerization of E -1,3-diene to its Z -isomer without photoirradiation, where kinetic trapping is achieved through rational sequences of dinuclear elementary steps. The chemical energy required for the E to Z isomerization can be injected from an organic conjugate reaction through sharing of common Pd species. Geometric E to Z double C=C bond isomerization is challenging as it requires kinetic trapping of the Z -isomer with injection of chemical energy. Here, the authors report a dinuclear Pd(I)−Pd(I) complex that mediates selective isomerization of E -1,3-dienes to the Z -isomers without photoirradiation.
AbstractList Abstract The E / Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily addressable by thermal Z to E geometric isomerization through equilibrium, it has remained difficult to undergo thermal geometric isomerization to the reverse E to Z direction in a selective manner, because it requires kinetic trapping of Z -isomer with injection of chemical energy. Here we report that a dinuclear Pd I −Pd I complex mediates selective isomerization of E -1,3-diene to its Z -isomer without photoirradiation, where kinetic trapping is achieved through rational sequences of dinuclear elementary steps. The chemical energy required for the E to Z isomerization can be injected from an organic conjugate reaction through sharing of common Pd species.
The E / Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily addressable by thermal Z to E geometric isomerization through equilibrium, it has remained difficult to undergo thermal geometric isomerization to the reverse E to Z direction in a selective manner, because it requires kinetic trapping of Z -isomer with injection of chemical energy. Here we report that a dinuclear Pd I −Pd I complex mediates selective isomerization of E -1,3-diene to its Z -isomer without photoirradiation, where kinetic trapping is achieved through rational sequences of dinuclear elementary steps. The chemical energy required for the E to Z isomerization can be injected from an organic conjugate reaction through sharing of common Pd species. Geometric E to Z double C=C bond isomerization is challenging as it requires kinetic trapping of the Z -isomer with injection of chemical energy. Here, the authors report a dinuclear Pd(I)−Pd(I) complex that mediates selective isomerization of E -1,3-dienes to the Z -isomers without photoirradiation.
The E/Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily addressable by thermal Z to E geometric isomerization through equilibrium, it has remained difficult to undergo thermal geometric isomerization to the reverse E to Z direction in a selective manner, because it requires kinetic trapping of Z-isomer with injection of chemical energy. Here we report that a dinuclear PdI−PdI complex mediates selective isomerization of E-1,3-diene to its Z-isomer without photoirradiation, where kinetic trapping is achieved through rational sequences of dinuclear elementary steps. The chemical energy required for the E to Z isomerization can be injected from an organic conjugate reaction through sharing of common Pd species.Geometric E to Z double C=C bond isomerization is challenging as it requires kinetic trapping of the Z-isomer with injection of chemical energy. Here, the authors report a dinuclear Pd(I)−Pd(I) complex that mediates selective isomerization of E-1,3-dienes to the Z-isomers without photoirradiation.
The E/Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily addressable by thermal Z to E geometric isomerization through equilibrium, it has remained difficult to undergo thermal geometric isomerization to the reverse E to Z direction in a selective manner, because it requires kinetic trapping of Z-isomer with injection of chemical energy. Here we report that a dinuclear PdI-PdI complex mediates selective isomerization of E-1,3-diene to its Z-isomer without photoirradiation, where kinetic trapping is achieved through rational sequences of dinuclear elementary steps. The chemical energy required for the E to Z isomerization can be injected from an organic conjugate reaction through sharing of common Pd species.
Geometric E to Z double C=C bond isomerization is challenging as it requires kinetic trapping of the Z-isomer with injection of chemical energy. Here, the authors report a dinuclear Pd(I)−Pd(I) complex that mediates selective isomerization of E-1,3-dienes to the Z-isomers without photoirradiation.
The E/Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily addressable by thermal Z to E geometric isomerization through equilibrium, it has remained difficult to undergo thermal geometric isomerization to the reverse E to Z direction in a selective manner, because it requires kinetic trapping of Z-isomer with injection of chemical energy. Here we report that a dinuclear Pd -Pd complex mediates selective isomerization of E-1,3-diene to its Z-isomer without photoirradiation, where kinetic trapping is achieved through rational sequences of dinuclear elementary steps. The chemical energy required for the E to Z isomerization can be injected from an organic conjugate reaction through sharing of common Pd species.
ArticleNumber 1473
Author Kudo, Eiji
Kawamata, Shiori
Sasaki, Kota
Yamamoto, Koji
Murahashi, Tetsuro
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  surname: Kudo
  fullname: Kudo, Eiji
  organization: Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology
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  surname: Sasaki
  fullname: Sasaki, Kota
  organization: Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology
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  givenname: Shiori
  surname: Kawamata
  fullname: Kawamata, Shiori
  organization: Research Center of Integrative Molecular Science (CIMoS), Institute for Molecular Science
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  givenname: Koji
  surname: Yamamoto
  fullname: Yamamoto, Koji
  organization: Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology
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  givenname: Tetsuro
  orcidid: 0000-0002-2288-0681
  surname: Murahashi
  fullname: Murahashi, Tetsuro
  email: mura@apc.titech.ac.jp
  organization: Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology
BackLink https://www.ncbi.nlm.nih.gov/pubmed/33674574$$D View this record in MEDLINE/PubMed
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SSID ssj0000391844
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Snippet The E / Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily addressable...
The E/Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily addressable by...
Abstract The E / Z stereocontrol in a C=C bond is a fundamental issue in olefin synthesis. Although the thermodynamically more stable E geometry is readily...
Geometric E to Z double C=C bond isomerization is challenging as it requires kinetic trapping of the Z-isomer with injection of chemical energy. Here, the...
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StartPage 1473
SubjectTerms 119/118
140/131
140/58
639/638/263/406/910
639/638/403/935
639/638/549/933
Carbon
Chemical energy
Dienes
Energy
Equilibrium
Humanities and Social Sciences
Injection
Isomerization
Isomers
multidisciplinary
Science
Science (multidisciplinary)
Trapping
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Title Selective E to Z isomerization of 1,3-Dienes Enabled by A Dinuclear Mechanism
URI https://link.springer.com/article/10.1038/s41467-021-21720-4
https://www.ncbi.nlm.nih.gov/pubmed/33674574
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Volume 12
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