C–C bond activation enabled by dyotropic rearrangement of Pd(iv) species

The weak carbon–metal bond combined with the kinetic inertness of the carbon–carbon bond renders metal-catalysed C–C bond activation to be highly challenging. Most of the reported C–C bond activation methodologies involve strain-releasing cleavage of small rings to compensate for unfavourable kineti...

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Published inNature chemistry Vol. 13; no. 7; pp. 671 - 676
Main Authors Cao, Jian, Wu, Hua, Wang, Qian, Zhu, Jieping
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 01.07.2021
NATURE PORTFOLIO
Nature Publishing Group
Subjects
639/638/403/933
639/638/549/933
639/638/77/883
639/638/77/888
Analytical Chemistry
Biochemistry
Bonding
Carbon
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Cleavage
Covalent bonds
Enantiomers
Fluorination
Inorganic Chemistry
Organic Chemistry
Palladium
Physical Chemistry
Physical Sciences
Science & Technology
Synthesis
SYMMETRY CONTROLLED REACTIONS
PALLADIUM
ALKENES
AMINATION
PD(III)
CONSTRUCTION
COMPLEXES
CLEAVAGE
REDUCTIVE ELIMINATION
Online AccessGet full text
ISSN1755-4330
1755-4349
1755-4349
DOI10.1038/s41557-021-00698-y

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Abstract The weak carbon–metal bond combined with the kinetic inertness of the carbon–carbon bond renders metal-catalysed C–C bond activation to be highly challenging. Most of the reported C–C bond activation methodologies involve strain-releasing cleavage of small rings to compensate for unfavourable kinetic and thermodynamic penalties associated with C–C bond cleavage. Here we report that the 1,2-positional interchange of vicinal C–C and C–Pd( iv ) bonds (dyotropic rearrangement) can be realized in a stereospecific manner under mild conditions, giving access to quaternary carbon–palladium bonds. An enantioselective synthesis of medicinally relevant fluorinated cyclopentanes, featuring this rearrangement as a key step, has been developed. We anticipate that implementing a Pd-based dyotropic rearrangement in reaction design could provide a new tool in the development of Pd-catalysed transformations. Many C–C bond activation methods involve strain-releasing cleavage of small rings to compensate for unfavourable kinetics and thermodynamics. Now, the 1,2-positional interchange of vicinal C–C and C–Pd bonds has been reported, giving access to quaternary carbon–palladium bonds. This dyotropic rearrangement has been used for the enantioselective synthesis of functionalized fluorinated cyclopentanes.
AbstractList The weak carbon-metal bond combined with the kinetic inertness of the carbon-carbon bond renders metal-catalysed C-C bond activation to be highly challenging. Most of the reported C-C bond activation methodologies involve strain-releasing cleavage of small rings to compensate for unfavourable kinetic and thermodynamic penalties associated with C-C bond cleavage. Here we report that the 1,2-positional interchange of vicinal C-C and C-Pd(IV) bonds (dyotropic rearrangement) can be realized in a stereospecific manner under mild conditions, giving access to quaternary carbon-palladium bonds. An enantioselective synthesis of medicinally relevant fluorinated cyclopentanes, featuring this rearrangement as a key step, has been developed. We anticipate that implementing a Pd-based dyotropic rearrangement in reaction design could provide a new tool in the development of Pd-catalysed transformations.The weak carbon-metal bond combined with the kinetic inertness of the carbon-carbon bond renders metal-catalysed C-C bond activation to be highly challenging. Most of the reported C-C bond activation methodologies involve strain-releasing cleavage of small rings to compensate for unfavourable kinetic and thermodynamic penalties associated with C-C bond cleavage. Here we report that the 1,2-positional interchange of vicinal C-C and C-Pd(IV) bonds (dyotropic rearrangement) can be realized in a stereospecific manner under mild conditions, giving access to quaternary carbon-palladium bonds. An enantioselective synthesis of medicinally relevant fluorinated cyclopentanes, featuring this rearrangement as a key step, has been developed. We anticipate that implementing a Pd-based dyotropic rearrangement in reaction design could provide a new tool in the development of Pd-catalysed transformations.
The weak carbon-metal bond combined with the kinetic inertness of the carbon-carbon bond renders metal-catalysed C-C bond activation to be highly challenging. Most of the reported C-C bond activation methodologies involve strain-releasing cleavage of small rings to compensate for unfavourable kinetic and thermodynamic penalties associated with C-C bond cleavage. Here we report that the 1,2-positional interchange of vicinal C-C and C-Pd(IV) bonds (dyotropic rearrangement) can be realized in a stereospecific manner under mild conditions, giving access to quaternary carbon-palladium bonds. An enantioselective synthesis of medicinally relevant fluorinated cyclopentanes, featuring this rearrangement as a key step, has been developed. We anticipate that implementing a Pd-based dyotropic rearrangement in reaction design could provide a new tool in the development of Pd-catalysed transformations.
The weak carbon–metal bond combined with the kinetic inertness of the carbon–carbon bond renders metal-catalysed C–C bond activation to be highly challenging. Most of the reported C–C bond activation methodologies involve strain-releasing cleavage of small rings to compensate for unfavourable kinetic and thermodynamic penalties associated with C–C bond cleavage. Here we report that the 1,2-positional interchange of vicinal C–C and C–Pd(iv) bonds (dyotropic rearrangement) can be realized in a stereospecific manner under mild conditions, giving access to quaternary carbon–palladium bonds. An enantioselective synthesis of medicinally relevant fluorinated cyclopentanes, featuring this rearrangement as a key step, has been developed. We anticipate that implementing a Pd-based dyotropic rearrangement in reaction design could provide a new tool in the development of Pd-catalysed transformations.Many C–C bond activation methods involve strain-releasing cleavage of small rings to compensate for unfavourable kinetics and thermodynamics. Now, the 1,2-positional interchange of vicinal C–C and C–Pd bonds has been reported, giving access to quaternary carbon–palladium bonds. This dyotropic rearrangement has been used for the enantioselective synthesis of functionalized fluorinated cyclopentanes.
The weak carbon–metal bond combined with the kinetic inertness of carbon–carbon bond renders the metal catalyzed C–C bond activation to be highly challenging. Most of the reported C–C bond activation methodologies involve the strain-releasing cleavage of small rings to compensate the unfavorable kinetic and thermodynamic penalties associated with the C–C bond cleavage. Here we report that the 1,2-positional interchange of vicinal C–C and C–Pd(IV) bonds (dyotropic rearrangement) can be realized in a stereospecific manner under mild conditions, giving access to quaternary carbon-palladium bonds. An enantioselective synthesis of medicinally relevant fluorinated cyclopentanes, featuring this rearrangement as a key step, has been developed. We anticipate that implementing a Pd-based dyotropic rearrangement in reaction design could provide a new dimension in the development of Pd-catalyzed transformations.
The weak carbon–metal bond combined with the kinetic inertness of the carbon–carbon bond renders metal-catalysed C–C bond activation to be highly challenging. Most of the reported C–C bond activation methodologies involve strain-releasing cleavage of small rings to compensate for unfavourable kinetic and thermodynamic penalties associated with C–C bond cleavage. Here we report that the 1,2-positional interchange of vicinal C–C and C–Pd( iv ) bonds (dyotropic rearrangement) can be realized in a stereospecific manner under mild conditions, giving access to quaternary carbon–palladium bonds. An enantioselective synthesis of medicinally relevant fluorinated cyclopentanes, featuring this rearrangement as a key step, has been developed. We anticipate that implementing a Pd-based dyotropic rearrangement in reaction design could provide a new tool in the development of Pd-catalysed transformations. Many C–C bond activation methods involve strain-releasing cleavage of small rings to compensate for unfavourable kinetics and thermodynamics. Now, the 1,2-positional interchange of vicinal C–C and C–Pd bonds has been reported, giving access to quaternary carbon–palladium bonds. This dyotropic rearrangement has been used for the enantioselective synthesis of functionalized fluorinated cyclopentanes.
Author Wang, Qian
Wu, Hua
Cao, Jian
Zhu, Jieping
AuthorAffiliation 2 Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. China
1 Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH5304, CH-1015 Lausanne, Switzerland
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Issue 7
Keywords SYMMETRY CONTROLLED REACTIONS
PALLADIUM
ALKENES
AMINATION
PD(III)
CONSTRUCTION
COMPLEXES
CLEAVAGE
REDUCTIVE ELIMINATION
Language English
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NAT CHEM
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PublicationYear 2021
Publisher Nature Publishing Group UK
NATURE PORTFOLIO
Nature Publishing Group
Publisher_xml – name: Nature Publishing Group UK
– name: NATURE PORTFOLIO
– name: Nature Publishing Group
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SSID ssj0065316
Score 2.546751
Snippet The weak carbon–metal bond combined with the kinetic inertness of the carbon–carbon bond renders metal-catalysed C–C bond activation to be highly challenging....
The weak carbon-metal bond combined with the kinetic inertness of the carbon-carbon bond renders metal-catalysed C-C bond activation to be highly challenging....
The weak carbon–metal bond combined with the kinetic inertness of carbon–carbon bond renders the metal catalyzed C–C bond activation to be highly challenging....
Source Web of Science
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pubmed
webofscience
crossref
springer
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StartPage 671
SubjectTerms 639/638/403/933
639/638/549/933
639/638/77/883
639/638/77/888
Analytical Chemistry
Biochemistry
Bonding
Carbon
Chemistry
Chemistry and Materials Science
Chemistry, Multidisciplinary
Chemistry/Food Science
Cleavage
Covalent bonds
Enantiomers
Fluorination
Inorganic Chemistry
Organic Chemistry
Palladium
Physical Chemistry
Physical Sciences
Science & Technology
Synthesis
Title C–C bond activation enabled by dyotropic rearrangement of Pd(iv) species
URI https://link.springer.com/article/10.1038/s41557-021-00698-y
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https://www.ncbi.nlm.nih.gov/pubmed/34031566
https://www.proquest.com/docview/2546784960
https://www.proquest.com/docview/2532244462
https://pubmed.ncbi.nlm.nih.gov/PMC7611116
Volume 13
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