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Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes.

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Title: Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes.
Authors: Ji Yang, Jiawang Liu, Neumann, Helfried, Franke, Robert, Jackstell, Ralf, Beller, Matthias
Source: Science (pre-March 2025). 12/20/2019, Vol. 366 Issue 6472, p1514-1517. 4p. 2 Color Photographs, 1 Diagram.
Subjects: Pyridyl compounds, Phosphine, Catalysis, Butadiene, Carbon monoxide, Palladium catalysts, Carbonylation, Butanol
Abstract: The direct carbonylation of 1,3-butadiene offers the potential for a more cost-efficient and environmentally benign route to industrially important adipic acid derivatives. However, owing to the complex reaction network of regioisomeric carbonylation and isomerization pathways, a selective practical catalyst for this process has thus far proven elusive. Here, we report the design of a pyridyl-substituted bidentate phosphine ligand (HeMaRaphos) that, upon coordination to palladium, catalyzes adipate diester formation from 1,3-butadiene, carbon monoxide, and butanol with 97% selectivity and 100% atom-economy under industrially viable and scalable conditions (turnover number > 60,000). This catalyst system also affords access to a variety of other di- and triesters from 1,2- and 1,3-dienes. [ABSTRACT FROM AUTHOR]
Copyright of Science (pre-March 2025) is the property of American Association for the Advancement of Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Psychology and Behavioral Sciences Collection
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  Data: Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes.
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  Data: <searchLink fieldCode="AR" term="%22Ji+Yang%22">Ji Yang</searchLink><br /><searchLink fieldCode="AR" term="%22Jiawang+Liu%22">Jiawang Liu</searchLink><br /><searchLink fieldCode="AR" term="%22Neumann%2C+Helfried%22">Neumann, Helfried</searchLink><br /><searchLink fieldCode="AR" term="%22Franke%2C+Robert%22">Franke, Robert</searchLink><br /><searchLink fieldCode="AR" term="%22Jackstell%2C+Ralf%22">Jackstell, Ralf</searchLink><br /><searchLink fieldCode="AR" term="%22Beller%2C+Matthias%22">Beller, Matthias</searchLink>
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  Data: <searchLink fieldCode="JN" term="%22Science+%28pre-March+2025%29%22">Science (pre-March 2025)</searchLink>. 12/20/2019, Vol. 366 Issue 6472, p1514-1517. 4p. 2 Color Photographs, 1 Diagram.
– Name: Subject
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  Data: <searchLink fieldCode="DE" term="%22Pyridyl+compounds%22">Pyridyl compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Phosphine%22">Phosphine</searchLink><br /><searchLink fieldCode="DE" term="%22Catalysis%22">Catalysis</searchLink><br /><searchLink fieldCode="DE" term="%22Butadiene%22">Butadiene</searchLink><br /><searchLink fieldCode="DE" term="%22Carbon+monoxide%22">Carbon monoxide</searchLink><br /><searchLink fieldCode="DE" term="%22Palladium+catalysts%22">Palladium catalysts</searchLink><br /><searchLink fieldCode="DE" term="%22Carbonylation%22">Carbonylation</searchLink><br /><searchLink fieldCode="DE" term="%22Butanol%22">Butanol</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: The direct carbonylation of 1,3-butadiene offers the potential for a more cost-efficient and environmentally benign route to industrially important adipic acid derivatives. However, owing to the complex reaction network of regioisomeric carbonylation and isomerization pathways, a selective practical catalyst for this process has thus far proven elusive. Here, we report the design of a pyridyl-substituted bidentate phosphine ligand (HeMaRaphos) that, upon coordination to palladium, catalyzes adipate diester formation from 1,3-butadiene, carbon monoxide, and butanol with 97% selectivity and 100% atom-economy under industrially viable and scalable conditions (turnover number > 60,000). This catalyst system also affords access to a variety of other di- and triesters from 1,2- and 1,3-dienes. [ABSTRACT FROM AUTHOR]
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  Label:
  Group: Ab
  Data: <i>Copyright of Science (pre-March 2025) is the property of American Association for the Advancement of Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=pbh&AN=140501638
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1126/science.aaz1293
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 4
        StartPage: 1514
    Subjects:
      – SubjectFull: Pyridyl compounds
        Type: general
      – SubjectFull: Phosphine
        Type: general
      – SubjectFull: Catalysis
        Type: general
      – SubjectFull: Butadiene
        Type: general
      – SubjectFull: Carbon monoxide
        Type: general
      – SubjectFull: Palladium catalysts
        Type: general
      – SubjectFull: Carbonylation
        Type: general
      – SubjectFull: Butanol
        Type: general
    Titles:
      – TitleFull: Direct synthesis of adipic acid esters via palladium-catalyzed carbonylation of 1,3-dienes.
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            NameFull: Ji Yang
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            NameFull: Jiawang Liu
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            NameFull: Neumann, Helfried
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            NameFull: Franke, Robert
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            NameFull: Jackstell, Ralf
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            NameFull: Beller, Matthias
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            – D: 20
              M: 12
              Text: 12/20/2019
              Type: published
              Y: 2019
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              Value: 366
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              Value: 6472
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            – TitleFull: Science (pre-March 2025)
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