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...
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| Published in | Angewandte Chemie International Edition Vol. 58; no. 42; pp. 14882 - 14886 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
14.10.2019
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
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| Abstract | 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.
Pyridyl phosphonium salts react with cyanopyridines and B2pin2 to form 2,4‐bipyridines with complete regiocontrol. Mechanistic studies support a radical–radical coupling process between two boryl‐stabilized pyridyl radical anions rather than a Minisci‐type pathway, and the process is unique to pyridyl phosphonium salts. |
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| AbstractList | A pyridine-pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B
pin
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. 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. Abstract A pyridine–pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B 2 pin 2 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. 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. Pyridyl phosphonium salts react with cyanopyridines and B2pin2 to form 2,4‐bipyridines with complete regiocontrol. Mechanistic studies support a radical–radical coupling process between two boryl‐stabilized pyridyl radical anions rather than a Minisci‐type pathway, and the process is unique to pyridyl phosphonium salts. A pyridine-pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B(2)pin(2) 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. |
| Author | Alegre‐Requena, Juan V. Greenwood, Jacob W. McNally, Andrew Paton, Robert S. Koniarczyk, J. Luke |
| Author_xml | – sequence: 1 givenname: J. Luke orcidid: 0000-0002-1944-2197 surname: Koniarczyk fullname: Koniarczyk, J. Luke organization: Colorado State University – sequence: 2 givenname: Jacob W. orcidid: 0000-0001-8512-2864 surname: Greenwood fullname: Greenwood, Jacob W. organization: Colorado State University – sequence: 3 givenname: Juan V. orcidid: 0000-0002-0769-7168 surname: Alegre‐Requena fullname: Alegre‐Requena, Juan V. organization: Colorado State University – sequence: 4 givenname: Robert S. orcidid: 0000-0002-0104-4166 surname: Paton fullname: Paton, Robert S. email: Robert.Paton@colostate.edu organization: University of Oxford – sequence: 5 givenname: Andrew orcidid: 0000-0002-8651-1631 surname: McNally fullname: McNally, Andrew email: andy.mcnally@colostate.edu organization: Colorado State University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31400037$$D View this record in MEDLINE/PubMed |
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| Keywords | bipyridines ELECTRON radical anions phosphonium salts ARYLATION TRIPHENYL radical coupling C-H FUNCTIONALIZATION HETEROCYCLES SUBSTITUTIONS RATE CONSTANTS Minisci reaction CHEMISTRY ARYL RADICALS TRIFLUOROMETHYLATION |
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| Snippet | A pyridine–pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B2pin2 as an electron‐transfer reagent.... A pyridine-pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B(2)pin(2) as an electron-transfer reagent.... A pyridine-pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B pin as an electron-transfer reagent.... Abstract A pyridine–pyridine coupling reaction has been developed between pyridyl phosphonium salts and cyanopyridines using B 2 pin 2 as an electron‐transfer... |
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| SubjectTerms | bipyridines Chemical industry Chemistry Chemistry, Multidisciplinary Coupling Intermediates Minisci reaction phosphonium salts Physical Sciences Pyridines radical anions radical coupling Reagents Salts Science & Technology Selectivity |
| Title | A Pyridine–Pyridine Cross‐Coupling Reaction via Dearomatized Radical Intermediates |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.201906267 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000485607600001 https://www.ncbi.nlm.nih.gov/pubmed/31400037 https://www.proquest.com/docview/2301398713/abstract/ https://search.proquest.com/docview/2271835845 |
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