Organophotocatalytic\nRegioselective Silylation/Germylation\nand Cascade Cyclization of <i>N</i>‑Alkenyl α‑CF<sub>3</sub> Acrylamides: Access to Densely Functionalized 4‑Pyrrolin-2-ones

We report an organophotoredox-catalyzed silylation/germylation\ncascade cyclization of <i>N</i>-alkenyl α-CF<sub>3</sub> acrylamides under mild conditions. <i>N</i>-Aminopyridinium\nsalts act as hydrogen atom transfer reagents under photoredox catalysis\nin the generation of silyl and germyl radicals. An array of silyl-\nand germyl-substituted 3-CF<sub>3</sub>-4-pyrrolin-2-one derivatives\nwere constructed in a shorter reaction time with low catalyst loading\nin good to excellent yields at room temperature. Importantly, this\nprotocol is amenable to the late-stage diversification of bioactive\nmolecules, as well as to large-scale synthesis.

Publication Details

Journal
Figshare
Published
2024-10-21
DOI
https://doi.org/10.1021/acs.orglett.4c03427.s001
Primary Topic
Agricultural Practices and Plant Genetics
Type
article
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article

Organophotocatalytic\nRegioselective Silylation/Germylation\nand Cascade Cyclization of N‑Alkenyl α‑CF3 Acrylamides: Access to Densely Functionalized 4‑Pyrrolin-2-ones

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Agricultural Practices and Plant Genetics
article

Organophotocatalytic\nRegioselective Silylation/Germylation\nand Cascade Cyclization of N‑Alkenyl α‑CF3 Acrylamides: Access to Densely Functionalized 4‑Pyrrolin-2-ones

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Abstract

We report an organophotoredox-catalyzed silylation/germylation\ncascade cyclization of <i>N</i>-alkenyl α-CF<sub>3</sub> acrylamides under mild conditions. <i>N</i>-Aminopyridinium\nsalts act as hydrogen atom transfer reagents under photoredox catalysis\nin the generation of silyl and germyl radicals. An array of silyl-\nand germyl-substituted 3-CF<sub>3</sub>-4-pyrrolin-2-one derivatives\nwere constructed in a shorter reaction time with low catalyst loading\nin good to excellent yields at room temperature. Importantly, this\nprotocol is amenable to the late-stage diversification of bioactive\nmolecules, as well as to large-scale synthesis.

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Agricultural Practices and Plant Genetics
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