Synthesis of an Eccentric Electron-Deficient Fluorinated Motif, Tetrafluoro-λ 6 -sulfanyl gem -Difluorocyclopropenes

Fluoro-functionalization is now recognized as a critical strategy in drug discovery; however, the accessible fluoro-functional groups are limited. We herein introduce an eccentric, fully fluorinated motif, -tetrafluoro-λ -sulfanyl -difluorocyclopropene . This novel motif is highly lipophilic and pol...

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Veröffentlicht in:Organic letters 2022-03, Vol.24 (8), p.1722-1726
Hauptverfasser: Maruno, Koki, Niina, Kiyoteru, Nagata, Osamu, Shibata, Norio
Format: Artikel
Sprache:eng
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Zusammenfassung:Fluoro-functionalization is now recognized as a critical strategy in drug discovery; however, the accessible fluoro-functional groups are limited. We herein introduce an eccentric, fully fluorinated motif, -tetrafluoro-λ -sulfanyl -difluorocyclopropene . This novel motif is highly lipophilic and polarized, enabling a connection of two independent groups via three continuous atoms with a large angle of pseudo configuration. The target motif was synthesized via a [2+1] cycloaddition of electron-deficient (hetero)aryl-SF -alkynes with an electrophilic difluorocarbene source.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00358