35779-07-8

Upstream product

• 125231-41-6 1-phenyl-3-(2,3,5,6-tetrafluoro-4-phenoxyphenyl)prop-2-en-1-one 
• 50-01-1 guanidine hydrochloride 
• 769-39-1 2,3,5,6-tetraflourophenol 
• 363-72-4 Pentafluorobenzene 
• 108-95-2 phenol 

Relevant academic research and scientific papers

Reaction of polyfluorinated chalcones with guanidine

Reactions of polyfluorinated chalcones with guanidine in the presence of bases are accompanied by elimination of the polyfluorophenyl group. 3-(Pentafluorophenyl)-1-phenylprop-2-en-1-one and its derivatives reacted with guanidine under basic conditions to give 4-phenylpyrimidin-2-amine, polyfluorobenzenes, and Michael adducts, 3-(2-amino-4-phenylpyrimidin-5-yl)-3-(4-R-2,3,5,6-tetrafluorophenyl)-1-phenylpropan-1-ones. 1-(Pentafluorophenyl)-3-phenylprop-2-en-1-one and 1,3-bis(pentafluorophenyl)prop-2-en-1-one were converted into cinnamic acid derivatives whose reaction with guanidine afforded 2-amino-6-aryl-5,6-dihydropyrimidin-4(1H)-ones.

A counteranion triggered arylation strategy using diaryliodonium fluorides

A mild and transition metal-free counteranion triggered arylation strategy has been developed using diaryliodonium fluorides. The fluoride counteranion within the hypervalent iodonium species displays unusual reactivity that activates a phenolic O-H bond leading to electrophilic O-arylation. A wide range of phenols and diaryliodonium salts are compatible with this transformation under remarkably mild conditions. Furthermore, we pre-empt the wider implications of this strategy by demonstrating the compatibility of the arylation tactic with latent carbon nucleophiles.

Nucleophilic aryloxydefluorination of pentafluorobenzene without noble metal catalysis

1-Phenoxy-2,3,5,6-tetrafluorobenzene and 1-(40-fluorophenoxy)-2,3,5,6- tetrafluorobenzene were prepared in a quantitative yield from C 6F5H, ArOH and K2CO3 (DMF or DMSO, 120 8C, 9-11 h). The catalytic effect of Pd(OAc)2 in the presence of AgNO3 as claimed in Ref. [1] was not confirmed.

Synthesis of polyfluorinated aryl ethers via ligand-free palladium-catalyzed CF activation of pentafluorobenzene

An efficient, ligand-free palladium-catalyzed method for the cross coupling reaction of pentafluorobenzene with phenols was developed. This reaction proceeds via a highly selective CF bond activation in the 3-position and is compatible with a variety of functional groups, delivering polyfluorinated aryl ethers in moderate to excellent yields.

Selective C4-F bond cleavage/C-O bond formation of polyfluoroarenes with phenols and benzyl alcohols

A facile and efficient SNAr method for the synthesis of unsymmetrical polyfluoroaryl ethers via selective C4-F bond cleavage of pentafluorobenzene is reported. The reaction could proceed smoothly without the requirement of additional metals or ligands, and afford a series of the corresponding products in good to high yields. A wide variety of substituted phenols and alcohols provided 1,2,4,5-tetrafluoropheny ether derivatives in regioselective manner.