An Umpolung Approach to Acyclic 1,4‐Dicarbonyl Amides via Photoredox‐Generated Carbamoyl Radicals
A method for the generation and reaction of carbamoyl radicals from oxamate salts, followed by reaction with electron‐poor olefins, is described. The oxamate salt acts as a reductive quencher in the photoredox catalytic cycle, allowing mild and mass‐efficient formation of 1,4‐dicarbonyl products; a...
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| Published in | Chemistry : a European journal Vol. 29; no. 28; pp. e202300403 - n/a |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
16.05.2023
Wiley Subscription Services, Inc |
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| Online Access | Get full text |
| ISSN | 0947-6539 1521-3765 1521-3765 |
| DOI | 10.1002/chem.202300403 |
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| Abstract | A method for the generation and reaction of carbamoyl radicals from oxamate salts, followed by reaction with electron‐poor olefins, is described. The oxamate salt acts as a reductive quencher in the photoredox catalytic cycle, allowing mild and mass‐efficient formation of 1,4‐dicarbonyl products; a challenging transformation in the context of functionalized amide formation. Increased understanding has been obtained by the use of ab initio calculations, in support of experimental observations. Furthermore, steps have been taken towards an environmentally‐friendly protocol, by utilizing sodium as a cheap and low mass counterion, and demonstrating successful reactions using a metal‐free photocatalyst and a sustainable, non‐toxic solvent system.
Photoredox catalysis is used to generate carbamoyl radicals from oxamate salts. Addition to a range of electron‐poor olefins gives the 1,4‐amido‐carbonyl products in good yields. The reaction proceeds under mild conditions, and a transition metal or organic photocatalyst can be employed. |
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| AbstractList | A method for the generation and reaction of carbamoyl radicals from oxamate salts, followed by reaction with electron-poor olefins, is described. The oxamate salt acts as a reductive quencher in the photoredox catalytic cycle, allowing mild and mass-efficient formation of 1,4-dicarbonyl products; a challenging transformation in the context of functionalized amide formation. Increased understanding has been obtained by the use of ab initio calculations, in support of experimental observations. Furthermore, steps have been taken towards an environmentally-friendly protocol, by utilizing sodium as a cheap and low mass counterion, and demonstrating successful reactions using a metal-free photocatalyst and a sustainable, non-toxic solvent system. A method for the generation and reaction of carbamoyl radicals from oxamate salts, followed by reaction with electron‐poor olefins, is described. The oxamate salt acts as a reductive quencher in the photoredox catalytic cycle, allowing mild and mass‐efficient formation of 1,4‐dicarbonyl products; a challenging transformation in the context of functionalized amide formation. Increased understanding has been obtained by the use of ab initio calculations, in support of experimental observations. Furthermore, steps have been taken towards an environmentally‐friendly protocol, by utilizing sodium as a cheap and low mass counterion, and demonstrating successful reactions using a metal‐free photocatalyst and a sustainable, non‐toxic solvent system. Photoredox catalysis is used to generate carbamoyl radicals from oxamate salts. Addition to a range of electron‐poor olefins gives the 1,4‐amido‐carbonyl products in good yields. The reaction proceeds under mild conditions, and a transition metal or organic photocatalyst can be employed. A method for the generation and reaction of carbamoyl radicals from oxamate salts, followed by reaction with electron-poor olefins, is described. The oxamate salt acts as a reductive quencher in the photoredox catalytic cycle, allowing mild and mass-efficient formation of 1,4-dicarbonyl products; a challenging transformation in the context of functionalized amide formation. Increased understanding has been obtained by the use of ab initio calculations, in support of experimental observations. Furthermore, steps have been taken towards an environmentally-friendly protocol, by utilizing sodium as a cheap and low mass counterion, and demonstrating successful reactions using a metal-free photocatalyst and a sustainable, non-toxic solvent system.A method for the generation and reaction of carbamoyl radicals from oxamate salts, followed by reaction with electron-poor olefins, is described. The oxamate salt acts as a reductive quencher in the photoredox catalytic cycle, allowing mild and mass-efficient formation of 1,4-dicarbonyl products; a challenging transformation in the context of functionalized amide formation. Increased understanding has been obtained by the use of ab initio calculations, in support of experimental observations. Furthermore, steps have been taken towards an environmentally-friendly protocol, by utilizing sodium as a cheap and low mass counterion, and demonstrating successful reactions using a metal-free photocatalyst and a sustainable, non-toxic solvent system. |
| Author | Williams, Jason D. Leach, Stuart G. Kerr, William J. |
| Author_xml | – sequence: 1 givenname: Jason D. orcidid: 0000-0001-5449-5094 surname: Williams fullname: Williams, Jason D. organization: Research Center Pharmaceutical Engineering GmbH (RCPE) – sequence: 2 givenname: Stuart G. surname: Leach fullname: Leach, Stuart G. email: stuart.g.leach@gsk.com organization: Medicines Research Centre – sequence: 3 givenname: William J. orcidid: 0000-0002-1332-785X surname: Kerr fullname: Kerr, William J. email: w.kerr@strath.ac.uk organization: University of Strathclyde |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36862066$$D View this record in MEDLINE/PubMed |
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| Keywords | PHOTOCHEMICAL GENERATION amides ALKYL RADICALS ACIDS CATALYZED SYNTHESIS ACYL RADICALS radical reactions REACTIVITY photochemistry CHEMISTRY photoredox catalysis synthetic methods BETA-LACTAMS CYCLIZATION |
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| Snippet | A method for the generation and reaction of carbamoyl radicals from oxamate salts, followed by reaction with electron‐poor olefins, is described. The oxamate... A method for the generation and reaction of carbamoyl radicals from oxamate salts, followed by reaction with electron-poor olefins, is described. The oxamate... |
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| SubjectTerms | Alkenes Amides Chemistry Chemistry, Multidisciplinary photochemistry photoredox catalysis Physical Sciences radical reactions Radicals Science & Technology synthetic methods |
| Title | An Umpolung Approach to Acyclic 1,4‐Dicarbonyl Amides via Photoredox‐Generated Carbamoyl Radicals |
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