General method for the synthesis of enaminones via photocatalysis
Enaminones are key intermediates in the synthesis of several derivatives with important applications in medicinal chemistry. Furthermore, many marketed drugs feature the enaminone structural moiety. In this context, we have developed a photoredox and nickel catalytic system to rapidly forge the enam...
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| Language: | English |
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Beilstein-Institut
2025-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.116 |
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| author | Paula Pérez-Ramos Raquel G. Soengas Humberto Rodríguez-Solla |
| author_facet | Paula Pérez-Ramos Raquel G. Soengas Humberto Rodríguez-Solla |
| author_sort | Paula Pérez-Ramos |
| collection | DOAJ |
| description | Enaminones are key intermediates in the synthesis of several derivatives with important applications in medicinal chemistry. Furthermore, many marketed drugs feature the enaminone structural moiety. In this context, we have developed a photoredox and nickel catalytic system to rapidly forge the enaminone scaffold from 3-bromochromones via a Michael reaction of an amine with an electron-deficient alkene moiety and subsequent photocatalyzed debromination. With this dual catalytic system, a range of structurally diverse enaminone derivatives have been achieved in good yields with total trans selectivity. Mechanistic studies indicate that the key to the success of this process is the formation of an unexplored ternary Ni-complex with 3-bromochromone and a pyridinium salt, which is crucial for the effective activation of the α,β-unsaturated system towards the nucleophilic addition. |
| format | Article |
| id | doaj-art-f8aa88b5f2c6445ea442b6f079bebe0f |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-f8aa88b5f2c6445ea442b6f079bebe0f2025-08-20T03:56:37ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-07-012111535154310.3762/bjoc.21.1161860-5397-21-116General method for the synthesis of enaminones via photocatalysisPaula Pérez-Ramos0Raquel G. Soengas1Humberto Rodríguez-Solla2Department of Organic and Inorganic Chemistry, and Instituto Universitario de Química Organometálica Enrique Moles, University of Oviedo, Julián Clavería 8, 33006, Oviedo, Spain Department of Organic and Inorganic Chemistry, and Instituto Universitario de Química Organometálica Enrique Moles, University of Oviedo, Julián Clavería 8, 33006, Oviedo, Spain Department of Organic and Inorganic Chemistry, and Instituto Universitario de Química Organometálica Enrique Moles, University of Oviedo, Julián Clavería 8, 33006, Oviedo, Spain Enaminones are key intermediates in the synthesis of several derivatives with important applications in medicinal chemistry. Furthermore, many marketed drugs feature the enaminone structural moiety. In this context, we have developed a photoredox and nickel catalytic system to rapidly forge the enaminone scaffold from 3-bromochromones via a Michael reaction of an amine with an electron-deficient alkene moiety and subsequent photocatalyzed debromination. With this dual catalytic system, a range of structurally diverse enaminone derivatives have been achieved in good yields with total trans selectivity. Mechanistic studies indicate that the key to the success of this process is the formation of an unexplored ternary Ni-complex with 3-bromochromone and a pyridinium salt, which is crucial for the effective activation of the α,β-unsaturated system towards the nucleophilic addition.https://doi.org/10.3762/bjoc.21.116chromonesdehalogenationenaminonesnickelphotocatalysis |
| spellingShingle | Paula Pérez-Ramos Raquel G. Soengas Humberto Rodríguez-Solla General method for the synthesis of enaminones via photocatalysis Beilstein Journal of Organic Chemistry chromones dehalogenation enaminones nickel photocatalysis |
| title | General method for the synthesis of enaminones via photocatalysis |
| title_full | General method for the synthesis of enaminones via photocatalysis |
| title_fullStr | General method for the synthesis of enaminones via photocatalysis |
| title_full_unstemmed | General method for the synthesis of enaminones via photocatalysis |
| title_short | General method for the synthesis of enaminones via photocatalysis |
| title_sort | general method for the synthesis of enaminones via photocatalysis |
| topic | chromones dehalogenation enaminones nickel photocatalysis |
| url | https://doi.org/10.3762/bjoc.21.116 |
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