127783-73-7

Usage

Uses

Used in Organic Synthesis:
[1,1'-Biphenyl]-4-carboxylic acid, 4'-(trifluoroMethyl)-, Methyl ester is utilized as a key intermediate in organic synthesis for constructing more complex molecular structures. Its unique properties, including the trifluoromethyl group, contribute to the development of novel compounds with specific functionalities.
Used in Pharmaceutical Research:
In the pharmaceutical industry, [1,1'-Biphenyl]-4-carboxylic acid, 4'-(trifluoroMethyl)-, Methyl ester serves as a building block for the creation of new drug candidates. Its versatile properties allow for the design of molecules with enhanced biological activity, potentially leading to the discovery of innovative treatments for various diseases.
Used in Agrochemical Development:
[1,1'-Biphenyl]-4-carboxylic acid, 4'-(trifluoroMethyl)-, Methyl ester may also find applications in the agrochemical sector. Its ability to improve the biological activity of molecules can be harnessed in the development of new pesticides or other agrochemical products, contributing to more effective and targeted solutions in agriculture.

Upstream product

• 619-42-1 4-methoxycarbonylphenyl bromide 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 98-56-6 4-chlorobenzotrifluoride 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 98-08-8 α,α,α-trifluorotoluene 
• 1571-08-0 methyl 4-formylbenzoate 
• 619-44-3 methyl 4-iodobenzoate 
• 188748-63-2 4-trifluoromethylphenyltriethoxysilane 
• 455-13-0 4-Iodobenzotrifluoride 
• 91734-76-8 methyl 4-tri-n-butylstannylbenzoate 
• 338396-06-8 methyl 4-((N, N-dimethylsulfamoyl)oxy)benzoate 
• 125102-17-2 (4-(trifluoromethyl)phenyl)zinc(II) chloride 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 

Downstream Products

• 457889-46-2 (4′-(trifluoromethyl)-[1,1′-biphenyl]-4-yl)methanol 
• 1417526-67-0 4-ethyl-5-(4'-(trifluoromethyl)biphenyl-4-yl)-4H-1,2,4-triazole-3-thiol 
• 1417526-68-1 4-ethyl-3-(4'-(trifluoromethyl)biphenyl-4-yl)-4H-1,2,4-triazole 
• 1417526-69-2 (4-ethyl-5-(4'-(trifluoromethyl)biphenyl-4-yl)-4H-1,2,4-triazol-3-yl)methanol 
• 1417526-70-5 3-(azido methyl)-4-ethyl-5-(4'-(trifluoromethyl)biphenyl-4-yl)-4H-1,2,4-triazole 
• 1417526-71-6 (4-ethyl-5-(4'-(trifluoromethyl)biphenyl-4-yl)-4H-1,2,4-triazol-3-yl)methanamine 
• 1417526-73-8 1-((4-ethyl-5-(4'-(trifluoromethyl)biphenyl-4-yl)-4H-1,2,4-triazol-3-yl)methyl)-2-thioxo-2,3,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-4(5H)-one 
• 1417527-29-7 1-((4-ethyl-5-(4'-(trifluoromethyl)biphenyl-4-yl)-4H-1,2,4-triazol-3-yl)methyl)-2-(4-fluorobenzylthio)-6,7-dihydro-1H-cyclopenta[d]pyrimidin-4(5H)-one 

Relevant academic research and scientific papers

Palladium-catalyzed cross-coupling reactions of arylsiloxanes with aryl halides: Application to solid-supported organic synthesis

The solid-phase version of the Pd-catalyzed Hiyama reaction between a variety of aryltriethoxysilanes and immobilized aryl halides was developed. Smooth cross-coupling was achieved to afford the corresponding biaryl products in moderate to excellent yields. The described protocol would be particularly useful for the construction of 4′-substituted 1,1′-biphenyl derivatives.

Cobalt-catalyzed C(sp2)?CN bond activation: Cross-electrophile coupling for biaryl formation and mechanistic insight

Herein, we report a cross-electrophile coupling of benzonitrile derivatives and aryl halides with a simple cobalt-based catalytic system under mild conditions to form biaryl compounds. Even though the cobalt catalyst is able to activate the C(sp2)?CN bond alone, the use of the AlMe3 Lewis acid enhances the reactivity of benzonitriles and improves the cross-selectivity with barely any influence on the functional group compatibility. X-ray structure determination of an original low-valent cobalt species combined with catalytic and stoichiometric reactions reveals a catalytically active cobalt(I) species toward the aryl halide partner. On the other hand, experimental insights, including cyclic voltammetry experiments, suggest the involvement of a cobalt complex of a lower oxidation state to activate the benzonitrile derivative. Finally, density functional theory calculations support the proposed mechanistic cycle involving two low-valent cobalt species of different oxidation states to perform the reaction.

'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

Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands

Catalysts based on the combination of Pd(OAc)2 and the electron-deficient phosphatrioxa-adamantane ligands are described for borylation of aryl bromides and chlorides. Catalytic evaluation of a small library of phosphatrioxa-adamantane ligands provided some insights on the preferred ligand steric profile for borylation reactions. The corresponding aryl boronate esters were accessed under mild conditions (25–70 °C) and isolated in high yields (up to 96%).

Palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides by carbon-nitrogen bond activation

Palladium-catalyzed Suzuki-Miyaura cross-coupling or aryl halides is widely employed in the synthesis of many important molecules in synthetic chemistry, including pharmaceuticals, polymers and functional materials. Herein, we disclose the first palladium-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of amides for the synthesis of biaryls through the selective activation of the N-C(O) bond of amides. This new method relies on the precise sequence engineering of the catalytic cycle, wherein decarbonylation occurs prior to the transmetallation step. The reaction is compatible with a wide range of boronic acids and amides, providing valuable biaryls in high yields (>60 examples). DFT studies support a mechanism involving oxidative addition, decarbonylation and transmetallation and provide insight into high N-C(O) bond activation selectivity. Most crucially, the reaction establishes the use of palladium catalysis in the biaryl Suzuki-Miyaura cross-coupling of the amide bond and should enable the design of a wide variety of cross-coupling methods in which palladium rivals the traditional biaryl synthesis from aryl halides and pseudohalides.

Acyl and Decarbonylative Suzuki Coupling of N-Acetyl Amides: Electronic Tuning of Twisted, Acyclic Amides in Catalytic Carbon-Nitrogen Bond Cleavage

We report the Pd-catalyzed acyl and the Ni-catalyzed biaryl Suzuki-Miyaura cross-coupling of N-acetyl-amides with arylboronic acids by selective N-C(O) cleavage. Activation of the amide bond by N-acylation provides electronically destabilized, acyclic, nonplanar amide, which readily undergoes cross-coupling with a wide range of boronic acids to produce biaryl ketones or biaryls in a highly efficient manner. Most crucially, the presented results introduce N-acetyl-amides as reactive acyclic amides in the emerging manifold of transition-metal-catalyzed amide cross-coupling. The scope and origin of high selectivity are discussed. Mechanistic studies point to remodeling of amidic resonance and amide bond twist as selectivity determining features in a unified strategy for cross-coupling of acyclic amides. Structural studies, mechanistic investigations as well as beneficial effects of the N-acyl substitution on cross-coupling of amides are reported.

GOLD-CATALYZED C-C CROSS-COUPLING OF BORON- AND SILICON-CONTAINING ARYL COMPOUNDS AND ARYLDIAZONIUM COMPOUNDS BY VISIBLE-LIGHT

The present invention relates to a method for producing (functionalized) biaryls by employing a visible-light-driven, gold-catalyzed C-C cross-coupling reaction system involving boron- and silicon-containing aryl compounds and aryldiazonium compounds. Moreover, the present invention relates to the use of such boron- and silicon-containing aryl compounds and aryldiazonium compounds, as well as related gold catalysts, in the manufacture of (functionalized) biaryls.

Photosensitizer-Free, Gold-Catalyzed C–C Cross-Coupling of Boronic Acids and Diazonium Salts Enabled by Visible Light

The first photosensitizer-free visible light-driven, gold-catalyzed C–C cross-couplings of arylboronic acids and aryldiazonium salts are reported. The reactions can be conducted under very mild conditions, using a catalytic amount of tris(4-trifluoromethyl)phosphinegold(I) chloride [(4-CF3-C6H4)3PAuCl] with methanol as the solvent allowing an alternative access to a variety of substituted biaryls in moderate to excellent yields with broad functional group tolerance. (Figure presented.).

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

Synthesis of Biaryls through Nickel-Catalyzed Suzuki-Miyaura Coupling of Amides by Carbon-Nitrogen Bond Cleavage

The first Ni-catalyzed Suzuki-Miyaura coupling of amides for the synthesis of widely occurring biaryl compounds through N-C amide bond activation is reported. The reaction tolerates a wide range of electron-withdrawing, electron-neutral, and electron-donating substituents on both coupling partners. The reaction constitutes the first example of the Ni-catalyzed generation of aryl electrophiles from bench-stable amides with potential applications for a broad range of organometallic reactions. Breaking and making: The first nickel-catalyzed Suzuki-Miyaura coupling of amides for the synthesis of biaryl compounds through N-C amide bond cleavage is reported. The reaction tolerates a wide range of sensitive and electronically diverse substituents on both coupling partners.