Selective Reductions of Complex Pyridines via NTf-Pyridinium Salts.
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| Title: | Selective Reductions of Complex Pyridines via NTf-Pyridinium Salts. |
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| Authors: | Josephitis, Celena1 (AUTHOR), McNally, Andrew1 (AUTHOR) Andy.McNally@colostate.edu |
| Source: | Synthesis. Jun2026, Vol. 58 Issue 11, p1259-1264. 6p. |
| Subjects: | Piperidine, Pyridinium compounds, Heterocyclic compounds, Hydrides, Catalysis, Chemical reduction, Pharmaceutical chemistry, Pyridine |
| Abstract: | Piperidines are widely found in biologically active compounds, and accessing these N-heterocycles from pyridines is a commonly used strategy. However, this approach is challenging when pyridines are embedded in complex structures, such as those found in pharmaceutical compounds. Here, we present a sequential approach to piperidines that commences with a hydride addition to NTf-activated pyridinium salts. In this method, we combined tris(pentafluorophenyl)borane as a catalyst with a silane reducing agent to achieve 4-selective mono-reduction, and then combined it with metal-catalyzed reductions to obtain tetrahydropiperidine and piperidine derivatives. The process operates on a broad range of pyridines with various functional groups and substitution patterns, as well as on pyridine-containing drugs. [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: 194135081 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: Selective Reductions of Complex Pyridines via NTf-Pyridinium Salts. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Josephitis%2C+Celena%22">Josephitis, Celena</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22McNally%2C+Andrew%22">McNally, Andrew</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> Andy.McNally@colostate.edu</i> – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Synthesis%22">Synthesis</searchLink>. Jun2026, Vol. 58 Issue 11, p1259-1264. 6p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Piperidine%22">Piperidine</searchLink><br /><searchLink fieldCode="DE" term="%22Pyridinium+compounds%22">Pyridinium compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Heterocyclic+compounds%22">Heterocyclic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Hydrides%22">Hydrides</searchLink><br /><searchLink fieldCode="DE" term="%22Catalysis%22">Catalysis</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+reduction%22">Chemical reduction</searchLink><br /><searchLink fieldCode="DE" term="%22Pharmaceutical+chemistry%22">Pharmaceutical chemistry</searchLink><br /><searchLink fieldCode="DE" term="%22Pyridine%22">Pyridine</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: Piperidines are widely found in biologically active compounds, and accessing these N-heterocycles from pyridines is a commonly used strategy. However, this approach is challenging when pyridines are embedded in complex structures, such as those found in pharmaceutical compounds. Here, we present a sequential approach to piperidines that commences with a hydride addition to NTf-activated pyridinium salts. In this method, we combined tris(pentafluorophenyl)borane as a catalyst with a silane reducing agent to achieve 4-selective mono-reduction, and then combined it with metal-catalyzed reductions to obtain tetrahydropiperidine and piperidine derivatives. The process operates on a broad range of pyridines with various functional groups and substitution patterns, as well as on pyridine-containing drugs. [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=194135081 |
| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1055/a-2784-2600 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 6 StartPage: 1259 Subjects: – SubjectFull: Piperidine Type: general – SubjectFull: Pyridinium compounds Type: general – SubjectFull: Heterocyclic compounds Type: general – SubjectFull: Hydrides Type: general – SubjectFull: Catalysis Type: general – SubjectFull: Chemical reduction Type: general – SubjectFull: Pharmaceutical chemistry Type: general – SubjectFull: Pyridine Type: general Titles: – TitleFull: Selective Reductions of Complex Pyridines via NTf-Pyridinium Salts. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Josephitis, Celena – PersonEntity: Name: NameFull: McNally, Andrew IsPartOfRelationships: – BibEntity: Dates: – D: 01 M: 06 Text: Jun2026 Type: published Y: 2026 Identifiers: – Type: issn-print Value: 00397881 Numbering: – Type: volume Value: 58 – Type: issue Value: 11 Titles: – TitleFull: Synthesis Type: main |
| ResultId | 1 |
