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

Org Lett

Department of Nanopharmaceutical Sciences and Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

Published: March 2022

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.

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http://dx.doi.org/10.1021/acs.orglett.2c00358DOI Listing

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