Synthesis of Trisubstituted Alkenes via Direct Oxidative Arene--Alkene Coupling.
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| Title: | Synthesis of Trisubstituted Alkenes via Direct Oxidative Arene--Alkene Coupling. |
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| Authors: | Jones, Roderick C.1, Gałęzowski, Michał1, O'Shea, Donal F.1 donal.f.oshea@ucd.ie |
| Source: | Journal of Organic Chemistry. 8/16/2013, Vol. 78 Issue 16, p8044-8053. 10p. |
| Subjects: | Acetic acid, Acetonitrile, Alkenes, Aromatic compounds, Intermediates (Chemistry) |
| Abstract: | The use of an inorganic oxidant with an acetic acid/acetonitrile solvent combination has been identified as optimal for direct arene/1,2-disubstituted alkene oxidative couplings, providing an efficient route to trisubstituted alkenes. The acetonitrile cosolvent dramatically accelerates the rate of reaction, and an insoluble inorganic oxidant limits unwanted oxidation of substrates. The scope of this procedure is illustrated with arenes and alkenes containing electron-donating and -withdrawing substituents resulting in a general synthetic strategy to trisubstituted alkenes. In situ ESI-MS analysis of the reaction components has identified the key Pd intermediates in the Fujiwara--Moritani catalytic cycle. [ABSTRACT FROM AUTHOR] |
| Copyright of Journal of Organic Chemistry is the property of American Chemical Society 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: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 90063126 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Synthesis of Trisubstituted Alkenes via Direct Oxidative Arene--Alkene Coupling. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Jones%2C+Roderick+C%2E%22">Jones, Roderick C.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Gałęzowski%2C+Michał%22">Gałęzowski, Michał</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22O'Shea%2C+Donal+F%2E%22">O'Shea, Donal F.</searchLink><relatesTo>1</relatesTo><i> donal.f.oshea@ucd.ie</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Organic+Chemistry%22">Journal of Organic Chemistry</searchLink>. 8/16/2013, Vol. 78 Issue 16, p8044-8053. 10p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Acetic+acid%22">Acetic acid</searchLink><br /><searchLink fieldCode="DE" term="%22Acetonitrile%22">Acetonitrile</searchLink><br /><searchLink fieldCode="DE" term="%22Alkenes%22">Alkenes</searchLink><br /><searchLink fieldCode="DE" term="%22Aromatic+compounds%22">Aromatic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Intermediates+%28Chemistry%29%22">Intermediates (Chemistry)</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: The use of an inorganic oxidant with an acetic acid/acetonitrile solvent combination has been identified as optimal for direct arene/1,2-disubstituted alkene oxidative couplings, providing an efficient route to trisubstituted alkenes. The acetonitrile cosolvent dramatically accelerates the rate of reaction, and an insoluble inorganic oxidant limits unwanted oxidation of substrates. The scope of this procedure is illustrated with arenes and alkenes containing electron-donating and -withdrawing substituents resulting in a general synthetic strategy to trisubstituted alkenes. In situ ESI-MS analysis of the reaction components has identified the key Pd intermediates in the Fujiwara--Moritani catalytic cycle. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Organic Chemistry is the property of American Chemical Society 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.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1021/jo401326f Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 10 StartPage: 8044 Subjects: – SubjectFull: Acetic acid Type: general – SubjectFull: Acetonitrile Type: general – SubjectFull: Alkenes Type: general – SubjectFull: Aromatic compounds Type: general – SubjectFull: Intermediates (Chemistry) Type: general Titles: – TitleFull: Synthesis of Trisubstituted Alkenes via Direct Oxidative Arene--Alkene Coupling. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Jones, Roderick C. – PersonEntity: Name: NameFull: Gałęzowski, Michał – PersonEntity: Name: NameFull: O'Shea, Donal F. IsPartOfRelationships: – BibEntity: Dates: – D: 16 M: 08 Text: 8/16/2013 Type: published Y: 2013 Identifiers: – Type: issn-print Value: 00223263 Numbering: – Type: volume Value: 78 – Type: issue Value: 16 Titles: – TitleFull: Journal of Organic Chemistry Type: main |
| ResultId | 1 |
