42875-02-5

Upstream product

• 434-64-0 perfluorotoluene 
• 108-95-2 phenol 
• 1394001-64-9 (PhB⁽¹⁸⁾O)3 
• 98-80-6 phenylboronic acid 

Downstream Products

• 42874-84-0 1,2,4,5-Tetrafluoro-3-(4-nitro-phenoxy)-6-trifluoromethyl-benzene 
• 108-95-2 phenol 

Relevant academic research and scientific papers

Photocatalytic hydrodefluorination: Facile access to partially fluorinated aromatics

Polyfluorinated aromatics are essential to materials science as well as the pharmaceutical and agrochemical industries and yet are often difficult to access. This Communication describes a photocatalytic hydrodefluorination approach which begins with easily accessible perfluoroarenes and selectively reduces the C-F bonds. The method allows facile access to a number of partially fluorinated arenes and takes place with unprecedented catalytic activity using a safe and inexpensive amine as the reductant.

Synthesis of unsymmetrical biaryl ethers through nickel-promoted coupling of polyfluoroarenes with arylboronic acids and oxygen

Polyfluoro-substituted unsymmetrical biaryl ethers were synthesized via a novel Ni-catalyzed cross-coupling reaction of polyfluoroarenes with arylboronic acids and oxygen. The polyfluorinated arenes presumably captured the phenoxide intermediate efficiently, which made the oxygen-insertion proceed smoothly via the SNAr protocol. The 18O labeling experiment demonstrated that the oxygen introduced into unsymmetrical diaryl ether originated from very trace amounts of oxygen in the reaction system. A plausible mechanism was also suggested.

Octafluorotoluene as a Reagent for the Selective Protection of Alcoholic and Phenolic Functions: Synthesis and Cleavage of Perfluorotolyl and other Perfluoroaryl Ethers of Steroids and Other Model Compounds

Heptafluorotolyl derivatives of phenol, of the steroids oestrone, oestradiol , cholesterol, testosterone, cortisol and 4-hydroxyandrostene-3,17-dione, of the phenyl-substituted alcohols 1- and 2-phenylethanol and 3-phenylpropanol and of catechol were prepared by phase-transfer catalysed reactions with octafluorotoluene.Reaction with sodium methoxide in dimethylformamide regenerated the alcohol or phenolic functions, by a stepwise process involving replacement of fluorine substituents by methoxyl followed by aryl-oxygen cleavage.Phenols were regenerated more rapidly than alcohols and could be deprotected selectively.The perfluorotolyl group was stable under reducing and oxidising conditions and was compatible with Grignard reagents.Pentafluoropyridine similarly, and more rapidly gave perfluoropyridyl derivatives of oestradiol , which could similarly be cleaved with sodium methoxide.Hexafluorobenzene was relatively unreactive under phase transfer conditions and its derivatives with oestrone was cleaved only with difficulty.Perfluoro-o-xylene reacted with catechol to give dibenzodioxin derivatives from which catechol was regenerated using sodium methoxide.

Heptafluoro-p-tolyl and Tetrafluoro-4-pyridyl as Novel and Selective Protecting Groups for Phenolic and Alcoholic Functions: Synthesis and Cleavage of Perfluoroaryl Ethers of Steroids

The easily prepared heptafluoro-p-tolyl and tetrafluoro-4-pyridyl ethers of a variety of steroids react with sodium methoxide in dimethylformamide to regenerate the parent steroid by a mechanism involving an aryl-oxygen cleavage.