1448804-06-5

Upstream product

• 352-34-1 4-fluoro-1-iodobenzene 
• 51-17-2 benzoimidazole 
• 363-72-4 Pentafluorobenzene 

Downstream Products

• 1610894-64-8 1-(4'-methoxy-2,3,5,6-tetra(1H-pyrazol-1-yl)-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole 
• 1610894-50-2 1-(2,3,5,6-tetrakis(4-methyl-1H-pyrazol-1-yl)phenyl)-1H-benzo[d]imidazole 
• 1610894-59-1 1-(2,3,5,6-tetrafluoro-4'-methoxybiphenyl-4-yl)-1H-benzo[d]imidazole 

Relevant academic research and scientific papers

Weakly nucleophilic potassium aryltrifluoroborates in palladium-catalyzed Suzuki-Miyaura reactions? Relative reactivity of K[4-RC6F4BF3] and the role of silver-assistance in acceleration of transmetallation

Small differences in the reactivity of weakly nucleophilic potassium aryltrifluoroborates are revealed in the silver-assisted Pd-catalyzed cross-coupling of K[4-RC6F4BF3] (R = H, Bu, MeO, EtO, PrO, iPrO, BuO, t-BuO, CH2=CHCH2O, PhCH2O, PhCH2CH2O, PhO, F, pyrazol-1-yl, pyrrol-1-yl, and indol-1-yl) with ArX (4-BrC6H4CH3, 4-IC6H4F and 3-IC6H4F). An assumed role of silver(I) compounds AgmY (Y = O, NO3, SO4, BF4, F) consists in polarization of the Pd-X bond in neutral complex ArPdLnX with the generation of the related transition state or formation of [ArPdLn][XAgmY] with a highly electrophilic cation and subsequent transmetallation with the weakly nucleophilic borate. Efficiency of AgmY as a polarizing agent decreases in order Ag2O > AgNO3 ≈ Ag2SO4 > Ag[BF4] > AgF. No clear correlation between the reactivity of K[4-RC6F4BF3] and substituent electron parameters, σI and σR °, of the aryl group 4-RC6F4 was found.

Sequential direct SNAr reactions of pentafluorobenzenes with azole or indole derivatives

Sequential regioselective N-arylations through high-yielding catalyst-free direct SNAr reactions of pentafluorobenzene derivatives with azole or indole derivatives are described. The N-arylated derivatives were further functionalized through a

Synthesis of potassium 4-(1-azol-1-yl)-2,3,5,6- tetrafluorophenyltrifluoroborates from K[C6F5BF 3] and alkali metal azol-1-ides. the dramatic distinction in nucleophilicity of alkali metal azol-1-ides and dialkylamides

Nucleophilic substitution of fluorine atom in K[C6F 5BF3] with alkali metal azol-1-ides in polar aprotic solvent (DMF, DMSO) at 60-130 C gives potassium 4-(azol-1-yl)-2,3,5,6- tetrafluorophenyltrifluoroborates, K[4-AzC6F4BF 3] (AzH = pyrrole, pyrazole, imidazole, indole, and benzimidazole). Unexpectedly, diethylamine and morpholine do not react with K[C 6F5BF3] under the same conditions while pentafluorobenzene and R2NC6F4H form at 150 C. Reaction of K[C6F5BF3] with Na[NR2] in diglyme or DMSO proceeds similar way. The assumed reason is the relatively low nucleophilicity of both secondary amines and alkali metal dialkylamides which results in destructive by-reaction with K[C6F 5BF3] rather than in its aminodefluorination. This is confirmed by the competitive nucleophilic aminodefluorination of a model substrate, C6F5Ph, with sodium indolide/sodium morpholinide.

Selective C4-F bond cleavage of pentafluorobenzene: Synthesis of N-tetrafluoroarylated heterocyclic compounds

A simple aromatic nucleophilic monosubstitution reaction for the synthesis of N-tetrafluoroarylated heterocyclic compounds via selective C4-F bond cleavage of pentafluorobenzene with N-H containing heterocycles is demonstrated. This method is highly tolerant of a wide range of substrates to give the corresponding products in moderate to good yields. Additionally, this strategy is applied to synthesize other mono-, di-, and tri-fluoroarylated indole derivatives. Crown Copyright