140483-60-9

Usage

Uses

4-Cyano-4''-(Trifluoromethyl)biphenyl

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 188748-63-2 4-trifluoromethylphenyltriethoxysilane 
• 36800-95-0 p-cyanophenyl p-toluenesulfonate 
• 2252-32-6 4-cyanophenyldiazonium tetrafluoroborate 
• 767-00-0 4-cyanophenol 
• 125102-17-2 (4-(trifluoromethyl)phenyl)zinc(II) chloride 
• 164648-84-4 4-cyanophenyl dimethylsulfamate 
• 623-03-0 4-Cyanochlorobenzene 
• 3058-39-7 4-iodobenzonitrile 
• 214360-44-8 2-(4-cyanophenyl)-5,5-dimethyl[1,3,2]dioxaborinane 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 455-13-0 4-Iodobenzotrifluoride 
• 540-80-7 tert.-butylnitrite 

Downstream Products

• 356058-18-9 (4'-(trifluoromethyl)[1,1'-biphenyl]-4-yl)methanamine 

Relevant academic research and scientific papers

Synthesis of biaryls and polyaryls by ligand-free Suzuki reaction in aqueous phase

A highly efficient palladium acetate-catalyzed ligand-free Suzuki reaction in aqueous phase was developed in short reaction times (0.5-1 h) at 35 °C in air. The key for such a successful catalytic system was the use of a suitable amount of cosolvents in the aqueous phase. The method could be extended to the consecutive multi-Suzuki coupling, and polyaryls were prepared in a single one-pot step in high selectivity and excellent yield under mild reaction conditions (60 °C).

Pd(OAc)2-biuret: A highly efficient, low cost and phosphine-free catalyst system for biaryl synthesis under aerobic conditions at room temperature

A highly efficient, less expensive and phosphine-free protocol for the Suzuki-Miyaura cross-coupling reactions of aryl halides and aryl boronic acids in iPrOH-H2O solvent under aerobic conditions has been developed. The results demonstrate that the biuret played a crucial role and making this protocol highly efficient. The Pd(OAc)2-biuret system exhibited superb catalytic activity towards the Suzuki-Miyaura cross-coupling reaction of a wide range of aryl halides with aryl boronic acids at room temperature, giving high yields even under very low catalytic loading. This system offers an attractive alternative to the existing protocols since the reaction proceeds in green solvent at room temperature with working simplicity, shorter reaction time, cost-effectiveness and provides the desired products in high yields. The effect of solvent, base as well as catalyst loading on the cross-coupling reaction of aryl halide with arylboronic acid is also described.

Simple and efficient phosphine-free Pd(OAc)2 catalyzed urea accelerated Suzuki-Miyaura cross-coupling reactions in iPrOH-H2O at room temperature

A simple, efficient, and less expensive protocol for the phosphine-free Suzuki-Miyaura cross-coupling reactions of aryl halides with different aryl boronic acids in iPrOH-H2O under aerobic conditions has been developed. The mixture of Pd(OAc)2 and urea catalyzes the Suzuki-Miyaura cross-coupling of a variety of aryl halides with aryl boronic acids at room temperature, giving generally high yields even under low catalytic loads. The effect of solvent, base, and catalyst loading on the coupling reaction of aryl halide with arylboronic acid is also described.

Overcoming Halide Inhibition of Suzuki-Miyaura Couplings with Biaryl Monophosphine-Based Catalysts

The Suzuki-Miyaura reaction is one of the most widely employed transformations in synthetic chemistry. Despite extensive investigation, questions remain about the mechanistic nature of the transmetalation step when catalysts based on advanced ligands such as biaryl monophosphines are used, impeding the development of improved catalysts. Here we demonstrate that the often overlooked halide salt (KX) generated as a byproduct of cross-coupling renders the transmetalation step reversible with SPhos-based catalysts, leading to severe reaction inhibition with (hetero)aryl iodides. Stoichiometric and kinetic studies reveal that halide inhibition likely originates from disfavoring the formation of a highly reactive Pd-OH intermediate. We demonstrate that changing the organic solvent in the biphasic reaction mixture from tetrahydrofuran to toluene is sufficient to minimize this inhibition and enable the general Suzuki-Miyaura coupling of (hetero)aryl iodides. Our studies suggest that halide inhibition may be a more general problem in cross-coupling reactions, especially those involving reversible transmetalation processes.

Suzuki coupling catalyzed by a homoleptic Pd(I)-Pd(I) solvento complex

The PdI-PdI bonded complex [Pd2(CH3CN)6][SbF6] 2 is catalytically active towards Suzuki cross-coupling reactions of aryl bromides or chlorides with various arylboronic acids under mild conditions giving good to excellent yields. Its performance is enhanced by the introduction of stoichiometric or limited phosphines. The effects of different ligands, metal oxidation states [Pd(II), Pd(I) Pd(0)], bases and solvents have been examined.

Biaryl Coupling of Aryldiazonium Salts and Arylboronic Acids Catalysed by Gold

A gold-catalysed coupling of aryldiazonium salts with arylboronic acids is described. The reactions proceed in satisfactory yields under irradiation with blue LEDs in the presence of KF and a catalytic amount of ascorbic acid. Notably, 4-nitrobenzendiazonium tetrafluoroborate is sufficiently reactive to undergo the coupling with a variety of arylboronic acids in the absence of aryl radical initiators. The coupling is applicable for electron-donating and electron-withdrawing groups present at the para, ortho, and meta positions of both substrates.

'Awaken' aryl sulfonyl fluoride: a new partner in the Suzuki-Miyaura coupling reaction

An example of the activation of the -SO2F group, which is traditionally considered a stable group even in the presence of a transition metal, is described using a novel partner in the Suzuki-Miyaura coupling reaction catalyzed by Pd(OAc)2 and Ruphos as ligands. The products showed good to outstanding yields and broad functional group compatibility under optimal conditions. The sequential synthesis of non-symmetric terphenyls and the gram grade process highlight the approach's synthetic utility. DFT calculations have shown that Pd0 prefers to insert between C-S bonds rather than S-F bonds. This journal is

Nickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes

Herein, we disclose a general and efficient method for the synthesis of Sb-aryl and Sb-alkyl stibines by the nickel-catalyzed cross-coupling of halostibines with organic halides. The synthesized Sb-aryl stibines couple with aryl halides to give biaryls efficiently via palladium catalysis. Sequential reactions of stibines with polyhalogenated arenes bearing active C–I/C–Br sites and inactive C–Cl sites successfully proceeded, resulting in the formation of a variety of complex molecules with good site selectivity. Drugs such as diflunisal and fenbufen, as well as a fenofibrate derivative, were synthesized on gram scales in good yields, together with the high recovery of chlorostibine. Furthermore, catalytic mechanisms are proposed based on the results of control experiments.

Complexes LNi(Cp)X with alkylamino-substituted N-heterocyclic carbene ligands (L) and their catalytic activity in the Suzuki—Miyaura reaction

New nickel(ii) complexes of the general formula LNi(Cp)X (L is an N-heterocyclic carbene (NHC) ligand of the 1,2,4-triazole or imidazole series; Cp is the cyclopentadienyl anion; X = Cl, I) are reported. In these complexes, the NHC ligands (L) contain an alkylamino group at the 3 or 4 position of the heterocycle. The synthesized complexes and structurally similar complexes without an alkylamino group were tested for catalytic activity in the Suzuki—Miyaura reaction. The introduction of an alkylamino group into the NHC ligand leads to the enhancement of the catalytic activity of complexes with N,N′-diaryl-substituted NHC ligands of the imidazole series and a decrease in the activity of the complexes with N,N′-dialkyl-substituted NHC ligands of the 1,2,4-triazole series.

Magnetic nanoparticles supported N-heterocyclic palladium complex: Synthesis and catalytic evaluations in Suzuki cross-coupling reaction

Because of the robustness and magnetic properties, the magnetic materials are promising and alternative candidate for the fabrication of noble metal in chemical catalysis from the viewpoint of green chemistry. Accordingly, an eco-friendly magnetic palladium catalyst loaded on N-Methylimidazole functionalized Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2-NMIM-Pd) has been designed and prepared in the present work. The resultant composite exhibited excellent catalytic activity towards the Suzuki cross-coupling reaction for the synthesis of the corresponding biaryls in good to excellent yields (up to 96%) under aerobic conditions. In particular, this catalyst could be easily recovered through magnetic separation in a few cycles. The as-prepared palladium complex showed advantages including high thermal stability, low toxicity, moisture and oxygen insensitivities in Suzuki reactions. More importantly, this study presents a catalysis system, which will provide the magnetic materials access to the potential applications in a wide range of green organic catalysis.