Photoredox-catalyzed 1,2-oxo-alkylation of vinyl arenes with 1,3-diketones: an approach to 1,4-dicarbonyls via C–C activation

A mild and inexpensive approach to synthesising a series of 1,4-diketones in moderate to excellent yields via 1,2-oxo alkylation has been developed using fluorescein as a photocatalyst and air as an oxidant. The key features include (i) varied substrate scope (39 examples); (ii) good functional grou...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2023-09, Vol.59 (76), p.11433-11436
Hauptverfasser: Palani, Pushbaraj, Arumugam, Ajithkumar, Raja, Dineshkumar, Muthu, Kesavan, Senadi, Gopal Chandru
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Sprache:eng
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Zusammenfassung:A mild and inexpensive approach to synthesising a series of 1,4-diketones in moderate to excellent yields via 1,2-oxo alkylation has been developed using fluorescein as a photocatalyst and air as an oxidant. The key features include (i) varied substrate scope (39 examples); (ii) good functional group tolerance; (iii) unsymmetrical 1,4-dicarbonyls; (iv) late-stage functionalization of thymol and ibuprofen derivatives; and (v) the synthetic expansion to 5- and 6-membered N-, O- and S-containing heterocycles.
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc02366d