Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation
Summary: Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical ar...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2018-11-01
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| Series: | iScience |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2589004218301846 |
| _version_ | 1819150505803251712 |
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| author | Joseph B. Sweeney Julien Doulcet Bimod Thapa |
| author_facet | Joseph B. Sweeney Julien Doulcet Bimod Thapa |
| author_sort | Joseph B. Sweeney |
| collection | DOAJ |
| description | Summary: Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical arsenal, including bimolecular alkene hydroarylation reactions. We report here a broad-scope, palladium-catalyzed pyrroline hydroarylation process that gives 3-aryl pyrrolidines, a class of small molecules with potency in a diverse range of biological scenarios. Thus, whereas N-acyl pyrrolines usually undergo palladium-catalyzed arylation to give alkene products, the corresponding reactions of N-alkyl pyrrolines deliver products of hydroarylation, pyrrolidines. The process has broad substrate scope and can be used to directly deliver drug-like molecules in a single step from readily available precursors. : Chemistry; Catalysis; Organic Synthesis Subject Areas: Chemistry, Catalysis, Organic Synthesis |
| first_indexed | 2024-12-22T14:18:35Z |
| format | Article |
| id | doaj.art-87fbdfa16f8944139ca4825d0cd432e1 |
| institution | Directory Open Access Journal |
| issn | 2589-0042 |
| language | English |
| last_indexed | 2024-12-22T14:18:35Z |
| publishDate | 2018-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | iScience |
| spelling | doaj.art-87fbdfa16f8944139ca4825d0cd432e12022-12-21T18:23:02ZengElsevieriScience2589-00422018-11-019328336Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed HydroarylationJoseph B. Sweeney0Julien Doulcet1Bimod Thapa2Department of Chemistry, Lancaster University, Lancaster LA1 4YB, UK; Corresponding authorDepartment of Chemical Sciences, University of Huddersfield, Huddersfield HD1 3DH, UKDepartment of Chemical Sciences, University of Huddersfield, Huddersfield HD1 3DH, UKSummary: Metal-catalyzed reactions have revolutionized synthetic chemistry, allowing access to unprecedented molecular architectures with powerful properties and activities. Nonetheless, some transformations remain sparse in number, or out of reach, even with the diverse modern catalytic chemical arsenal, including bimolecular alkene hydroarylation reactions. We report here a broad-scope, palladium-catalyzed pyrroline hydroarylation process that gives 3-aryl pyrrolidines, a class of small molecules with potency in a diverse range of biological scenarios. Thus, whereas N-acyl pyrrolines usually undergo palladium-catalyzed arylation to give alkene products, the corresponding reactions of N-alkyl pyrrolines deliver products of hydroarylation, pyrrolidines. The process has broad substrate scope and can be used to directly deliver drug-like molecules in a single step from readily available precursors. : Chemistry; Catalysis; Organic Synthesis Subject Areas: Chemistry, Catalysis, Organic Synthesishttp://www.sciencedirect.com/science/article/pii/S2589004218301846 |
| spellingShingle | Joseph B. Sweeney Julien Doulcet Bimod Thapa Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation iScience |
| title | Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation |
| title_full | Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation |
| title_fullStr | Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation |
| title_full_unstemmed | Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation |
| title_short | Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation |
| title_sort | synthesis of 3 substituted pyrrolidines via palladium catalyzed hydroarylation |
| url | http://www.sciencedirect.com/science/article/pii/S2589004218301846 |
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