Photoredox-Catalyzed\nRegioselective 1,3-Alkoxypyridylation\nof <i>gem</i>-Difluorocyclopropanes

Difluoromethylene and pyridine cores are very important\nstructural\nunits in medicinal chemistry. Herein, we report the development of\nphotoredox-catalyzed ring-opening and 1,3-alkoxypyridylation of <i>gem</i>-difluorinated cyclopropanes using 4-cyanopyrines and\nalcohols, employing cyclopropane radical cations as the key intermediate.\nThe reaction exhibits high regioselectivity under mild conditions\nand can also be practiced on gram-scale synthesis, telescoped reaction,\nand late-stage functionalization of biological molecules.

Publication Details

Journal
Figshare
Published
2024-12-04
DOI
https://doi.org/10.1021/acs.orglett.4c04169.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Photoredox-Catalyzed\nRegioselective 1,3-Alkoxypyridylation\nof gem-Difluorocyclopropanes

Figshare
Fluorine in Organic Chemistry
article

Photoredox-Catalyzed\nRegioselective 1,3-Alkoxypyridylation\nof gem-Difluorocyclopropanes

article en

Abstract

Difluoromethylene and pyridine cores are very important\nstructural\nunits in medicinal chemistry. Herein, we report the development of\nphotoredox-catalyzed ring-opening and 1,3-alkoxypyridylation of <i>gem</i>-difluorinated cyclopropanes using 4-cyanopyrines and\nalcohols, employing cyclopropane radical cations as the key intermediate.\nThe reaction exhibits high regioselectivity under mild conditions\nand can also be practiced on gram-scale synthesis, telescoped reaction,\nand late-stage functionalization of biological molecules.

Figshare
Openalex Percentile: Top 73%
Fluorine in Organic Chemistry
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Photoredox-Catalyzed\nRegioselective 1,3-Alkoxypyridylation\nof <i>gem</i>-Difluorocyclopropanes · Figshare (2024) | TGRS Research Map | TGRS