Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N -Alkenyl α-CF 3 Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones

We report an organophotoredox-catalyzed silylation/germylation cascade cyclization of -alkenyl α-CF acrylamides under mild conditions. -Aminopyridinium salts act as hydrogen atom transfer reagents under photoredox catalysis in the generation of silyl and germyl radicals. An array of silyl- and germy...

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Veröffentlicht in:Organic letters 2024-11, Vol.26 (43), p.9269-9275
Hauptverfasser: Bajya, Kalu Ram, Maurya, Shivam Kumar, Selvakumar, Sermadurai
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Sprache:eng
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Zusammenfassung:We report an organophotoredox-catalyzed silylation/germylation cascade cyclization of -alkenyl α-CF acrylamides under mild conditions. -Aminopyridinium salts act as hydrogen atom transfer reagents under photoredox catalysis in the generation of silyl and germyl radicals. An array of silyl- and germyl-substituted 3-CF -4-pyrrolin-2-one derivatives were constructed in a shorter reaction time with low catalyst loading in good to excellent yields at room temperature. Importantly, this protocol is amenable to the late-stage diversification of bioactive molecules, as well as to large-scale synthesis.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c03427