Chlorinative Cyclization of Aryl Alkynoates Using NCS and 9‑Mesityl-10-methyl­acridinium Perchlorate Photocatalyst

Chlorinative Cyclization of Aryl Alkynoates Using NCS and 9‑Mesityl-10-methyl­acridinium Perchlorate Photocatalyst

In a chlorinative cyclization, Mes-Acr-MeClO4 acted as a visible-light photocatalyst to obtain 3-chlorocoumarins from aryl alkynoates and N-chlorosuccinimide (NCS). The radical initiated reaction proceeded in a cascading manner via Cl– addition to alkynoates. Next, 5-exo-trig spirocyclization and su...

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Veröffentlicht in:Organic letters 2021-10, Vol.23 (20), p.8088-8092
Hauptverfasser: Pramanik, Milan, Mathuri, Ashis, Sau, Sudip, Das, Monojit, Mal, Prasenjit
Format: Artikel
Sprache:eng
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Zusammenfassung:In a chlorinative cyclization, Mes-Acr-MeClO4 acted as a visible-light photocatalyst to obtain 3-chlorocoumarins from aryl alkynoates and N-chlorosuccinimide (NCS). The radical initiated reaction proceeded in a cascading manner via Cl– addition to alkynoates. Next, 5-exo-trig spirocyclization and subsequent 1,2-ester migration led to the formation of C–C and C–Cl bonds.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03100