A pyridine–pyridine cross‐coupling reaction via dearomatized radical intermediates
A pyridine–pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B2pin2 as an electron‐transfer reagent. Complete regio‐ and cross‐selectivity are observed when forming a range of valuable 2,4′‐bipyridines. Phosphonium salts were found to be the onl...
| Glavni autori: | , , , , |
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| Format: | Journal article |
| Jezik: | English |
| Izdano: |
Wiley
2019
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| _version_ | 1826317633823178752 |
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| author | Koniarczyk, JL Greenwood, JW Alegre‐Requena, JV Paton, RS McNally, A |
| author_facet | Koniarczyk, JL Greenwood, JW Alegre‐Requena, JV Paton, RS McNally, A |
| author_sort | Koniarczyk, JL |
| collection | OXFORD |
| description | A pyridine–pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B2pin2 as an electron‐transfer reagent. Complete regio‐ and cross‐selectivity are observed when forming a range of valuable 2,4′‐bipyridines. Phosphonium salts were found to be the only viable radical precursors in this process, and mechanistic studies indicate that the process does not proceed through a Minisci‐type coupling involving a pyridyl radical. Instead, a radical–radical coupling process between a boryl phosphonium pyridyl radical and a boryl‐stabilized cyanopyridine radical explains the C−C bond‐forming step. |
| first_indexed | 2024-03-07T01:43:28Z |
| format | Journal article |
| id | oxford-uuid:979ebe7a-a70b-4505-825a-a0aa7a570d23 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2025-03-11T16:57:00Z |
| publishDate | 2019 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:979ebe7a-a70b-4505-825a-a0aa7a570d232025-02-24T13:35:47ZA pyridine–pyridine cross‐coupling reaction via dearomatized radical intermediatesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:979ebe7a-a70b-4505-825a-a0aa7a570d23EnglishSymplectic ElementsWiley2019Koniarczyk, JLGreenwood, JWAlegre‐Requena, JVPaton, RSMcNally, AA pyridine–pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B2pin2 as an electron‐transfer reagent. Complete regio‐ and cross‐selectivity are observed when forming a range of valuable 2,4′‐bipyridines. Phosphonium salts were found to be the only viable radical precursors in this process, and mechanistic studies indicate that the process does not proceed through a Minisci‐type coupling involving a pyridyl radical. Instead, a radical–radical coupling process between a boryl phosphonium pyridyl radical and a boryl‐stabilized cyanopyridine radical explains the C−C bond‐forming step. |
| spellingShingle | Koniarczyk, JL Greenwood, JW Alegre‐Requena, JV Paton, RS McNally, A A pyridine–pyridine cross‐coupling reaction via dearomatized radical intermediates |
| title | A pyridine–pyridine cross‐coupling reaction via dearomatized radical intermediates |
| title_full | A pyridine–pyridine cross‐coupling reaction via dearomatized radical intermediates |
| title_fullStr | A pyridine–pyridine cross‐coupling reaction via dearomatized radical intermediates |
| title_full_unstemmed | A pyridine–pyridine cross‐coupling reaction via dearomatized radical intermediates |
| title_short | A pyridine–pyridine cross‐coupling reaction via dearomatized radical intermediates |
| title_sort | pyridine pyridine cross coupling reaction via dearomatized radical intermediates |
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