(E)-Selective Defluorinative Diphenothiazination of Trifluoromethyl Styrenes.
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| Title: | (E)-Selective Defluorinative Diphenothiazination of Trifluoromethyl Styrenes. |
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| Authors: | Yang, Yun1 (AUTHOR), Ebel, Ben2 (AUTHOR), Oppel, Iris M.2 (AUTHOR), Patureau, Frederic W.1 (AUTHOR) frederic.patureau@rwth-aachen.de |
| Source: | Synthesis. Mar2026, Vol. 58 Issue 6, p632-638. 7p. |
| Subjects: | Trifluoromethyl compounds, Phenothiazine, Organic reaction mechanisms, Stereoselective reactions, Aromatic fluorine compounds, Nucleophilic substitution reactions |
| Abstract: | Alpha-trifluoromethyl styrenes have become a versatile and valuable platform in order to access a wide variety of fluorinated organic motifs over recent years. This is due to their propensity to accommodate diverse defluorinative radical or nucleophilic attacks, which can lead to highly functionalized fluorinated alkenes. In some cases, such as described herein, E / Z selectivity issues can arise. While Zhu showed in 2021 that indole and carbazole nucleophiles lead preferentially to the (Z)-fluoroalkenes, we found that phenothiazines reverse the selectivity toward the (E)-configured diphenothiazinated fluoroalkenes. A scope and diastereoselectivity model for this unexpected reversal is discussed. [ABSTRACT FROM AUTHOR] |
| Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart 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: 192265094 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: (E)-Selective Defluorinative Diphenothiazination of Trifluoromethyl Styrenes. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Yang%2C+Yun%22">Yang, Yun</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Ebel%2C+Ben%22">Ebel, Ben</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Oppel%2C+Iris+M%2E%22">Oppel, Iris M.</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Patureau%2C+Frederic+W%2E%22">Patureau, Frederic W.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> frederic.patureau@rwth-aachen.de</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Synthesis%22">Synthesis</searchLink>. Mar2026, Vol. 58 Issue 6, p632-638. 7p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Trifluoromethyl+compounds%22">Trifluoromethyl compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Phenothiazine%22">Phenothiazine</searchLink><br /><searchLink fieldCode="DE" term="%22Organic+reaction+mechanisms%22">Organic reaction mechanisms</searchLink><br /><searchLink fieldCode="DE" term="%22Stereoselective+reactions%22">Stereoselective reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Aromatic+fluorine+compounds%22">Aromatic fluorine compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Nucleophilic+substitution+reactions%22">Nucleophilic substitution reactions</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: Alpha-trifluoromethyl styrenes have become a versatile and valuable platform in order to access a wide variety of fluorinated organic motifs over recent years. This is due to their propensity to accommodate diverse defluorinative radical or nucleophilic attacks, which can lead to highly functionalized fluorinated alkenes. In some cases, such as described herein, E / Z selectivity issues can arise. While Zhu showed in 2021 that indole and carbazole nucleophiles lead preferentially to the (Z)-fluoroalkenes, we found that phenothiazines reverse the selectivity toward the (E)-configured diphenothiazinated fluoroalkenes. A scope and diastereoselectivity model for this unexpected reversal is discussed. [ABSTRACT FROM AUTHOR] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Synthesis is the property of Georg Thieme Verlag Stuttgart 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=egs&AN=192265094 |
| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1055/a-2735-9268 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 7 StartPage: 632 Subjects: – SubjectFull: Trifluoromethyl compounds Type: general – SubjectFull: Phenothiazine Type: general – SubjectFull: Organic reaction mechanisms Type: general – SubjectFull: Stereoselective reactions Type: general – SubjectFull: Aromatic fluorine compounds Type: general – SubjectFull: Nucleophilic substitution reactions Type: general Titles: – TitleFull: (E)-Selective Defluorinative Diphenothiazination of Trifluoromethyl Styrenes. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Yang, Yun – PersonEntity: Name: NameFull: Ebel, Ben – PersonEntity: Name: NameFull: Oppel, Iris M. – PersonEntity: Name: NameFull: Patureau, Frederic W. IsPartOfRelationships: – BibEntity: Dates: – D: 15 M: 03 Text: Mar2026 Type: published Y: 2026 Identifiers: – Type: issn-print Value: 00397881 Numbering: – Type: volume Value: 58 – Type: issue Value: 6 Titles: – TitleFull: Synthesis Type: main |
| ResultId | 1 |
