Synthesis of Partially Fluorinated Organic Compounds from Perfluoro-2-methyl-2-pentene and Phenol Derivatives

Abstract

The reactions of perfluoro-2-methyl-2-pentene with substituted phenols and some heterocyclic compounds containing OH group result in the substitution of the fluorine atom either exclusively at the internal multiple bond or at the terminal multiple bond of perfluoro-2-methyl-1-pentene formed by isomerization of the starting perfluoroolefin in the course of the reaction. The reaction pathway depends on the reaction conditions, base used, and substituents in the benzene ring. The structures of the compounds were confirmed by 1 H, 13 C, and 19 F NMR and IR spectroscopy.

Synthesis of Perfluoro Alkyl/Alkenyl Aryl Sulfide: C−S Coupling Reaction Using Hexafluoropropylene Dimer (HFPD) as a Building Block

“…Based on the synthetic application of perfluoroolefins, fluorine atoms connected to C=C bonds can be easily replaced by nucleophiles [25] . Furin and coworkers prepared a variety of fluorinated alkenyl aryl ethers from perfluoro (2‐methyl‐2‐ pentene) 1 and various phenol derivatives, [26] thiophenols should also be suitable for the synthesis of perfluoroalkenyl aryl sulfides under similar conditions, which was due to their comparatively stronger nucleophilicity.…”

The Use of 3,6-Pyridazinediones in Organic Synthesis and Chemical Biology

“…Pyridazinediones, exemplified by 1,2-dihydro-3,6-dioxo-1alkylpyridazine 38 are often functionalised by reaction with electrophiles. [50][51][52][53][54] The main issue with this reaction is the competition between O-and N-functionalisation (Scheme 8). To promote O-functionalisation hard electrophiles are employed (Scheme 8a), whereas N-functionalisation is promoted by the use of soft electrophiles (Scheme 8b).…”

“…Common reagents for the promotion of N-functionalisation include alkyl bromides, α,β-unsaturated compounds, α-halogenated ketones and perfluorinated alkenes. [50][51][52][53][54]…”

Application of Oxidative Ring Opening/Ring Closing by Reductive Amination Protocol for the Stereocontrolled Synthesis of Functionalized Azaheterocycles

“…The incorporation of the fluorine atom or a certain fluorinated moiety into a certain organic compounds has become a powerful tool to discover new chemical entities possessing unique physical, chemical, and biological properties in comparison to those of their nonfluorinated counterparts. [13][14][15] Recently, it has been estimated that about 30% of the newly approved drugs contain fluorine atoms. [16][17][18][19] In view of the importance of organofluorine chemistry in drug research, fluorinated azaheterocyles have received high attention.…”