Halogen Radical-Enabled\nDearomatization of <i>N</i>‑Arylpropiolamides via\nPhotoinduced Sequential Halogenation/Spirocyclization/Oxidation\nProcess

Here we report a strategy that eliminates the need for\nphotocatalysts\nand external additives, which provides an operable and mild method\nfor halogen radical-enabled dearomatization of <i>N</i>-arylpropiolamides\nunder an oxygen atmosphere at room temperature. The method is applicable\nto a wide range of substrates, extending beyond the limited scope\nof <i>p</i>-methoxyl <i>N</i>-phenylpropynamides.\nFurthermore, several functional synthetic intermediates and anticancer\nbioactive molecules were successfully derived from 3-halogenated\nazaspiro[4.5]trienones.

Publication Details

Journal
Figshare
Published
2024-12-04
DOI
https://doi.org/10.1021/acs.joc.4c02277.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Halogen Radical-Enabled\nDearomatization of N‑Arylpropiolamides via\nPhotoinduced Sequential Halogenation/Spirocyclization/Oxidation\nProcess

Figshare
Catalytic C–H Functionalization Methods
article

Halogen Radical-Enabled\nDearomatization of N‑Arylpropiolamides via\nPhotoinduced Sequential Halogenation/Spirocyclization/Oxidation\nProcess

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Abstract

Here we report a strategy that eliminates the need for\nphotocatalysts\nand external additives, which provides an operable and mild method\nfor halogen radical-enabled dearomatization of <i>N</i>-arylpropiolamides\nunder an oxygen atmosphere at room temperature. The method is applicable\nto a wide range of substrates, extending beyond the limited scope\nof <i>p</i>-methoxyl <i>N</i>-phenylpropynamides.\nFurthermore, several functional synthetic intermediates and anticancer\nbioactive molecules were successfully derived from 3-halogenated\nazaspiro[4.5]trienones.

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Catalytic C–H Functionalization Methods
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Halogen Radical-Enabled\nDearomatization of <i>N</i>‑Arylpropiolamides via\nPhotoinduced Sequential Halogenation/Spirocyclization/Oxidation\nProcess · Figshare (2024) | TGRS Research Map | TGRS