Litcius/Paper detail

Single C–F Transformations of <i>o</i>-Hydrosilyl Benzotrifluorides with Trityl Compounds as All-in-One Reagents

Rika Idogawa, Young‐Chan Kim, Ken Shimomori, Takamitsu Hosoya, Suguru Yoshida

2020Organic Letters55 citationsDOI

Abstract

A facile method to prepare difluoromethylenes, including α,α-difluorobenzyl chlorides, by single C-F transformations of benzotrifluorides is disclosed. The C-F cleavage followed by chlorination proceeded smoothly using trityl chloride through the generation of trityl cation as an activator and chloride anion as a nucleophile. Diverse difluoromethylenes such as difluorobenzyl ethers were efficiently prepared by virtue of the good versatility of the resulting chloro and fluorosilyl groups.

Topics & Concepts

ChemistryReagentNucleophileChlorideCleavage (geology)IonCombinatorial chemistryOrganic chemistryMedicinal chemistryCatalysisFracture (geology)Geotechnical engineeringEngineeringFluorine in Organic ChemistryCyclopropane Reaction MechanismsInorganic Fluorides and Related Compounds