2714-87-6

Usage

Uses

Used in Pharmaceutical Industry:
[1,1'-Biphenyl]-4-carbonyl fluoride is used as a fluorinating agent for introducing fluorine atoms into organic molecules. The application reason is that the introduction of fluorine can lead to improved pharmacological properties of the resulting compounds, making it a valuable tool in drug discovery and development.
Used in Organic and Medicinal Chemistry:
[1,1'-Biphenyl]-4-carbonyl fluoride is used as a reagent in the synthesis of various fluorinated building blocks and intermediates. The application reason is its reactivity, which allows for selective fluorination of specific positions on organic molecules, making it a useful tool in the development of new chemical compounds and pharmaceuticals.

Upstream product

• 92-92-2 biphenyl-4-carboxylic acid 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 98-80-6 phenylboronic acid 
• 1612253-45-8 4-(((trifluoromethyl)sulfonyl)methyl)-1,1'-biphenyl 
• 2567-29-5 p-phenylbenzyl bromide 
• 3597-91-9 biphenyl-4-yl methanol 
• 3218-36-8 4-Phenylbenzaldehyde 
• 25327-57-5 [1,1′-biphenyl]-4-carboxylic anhydride 
• 73790-13-3 α,α-difluoro-4-phenylbenzeneacetic acid 
• 73789-98-7 2-([1,1'-biphenyl]-4-yl)-2,2-difluoroacetic acid ethyl ester 
• 1591-31-7 4-iodo-biphenyl 

Downstream Products

• 92-52-4 biphenyl 
• 3218-36-8 4-Phenylbenzaldehyde 
• 144432-80-4 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 720-75-2 methyl 4-phenylbenzoate 
• 15784-39-1 4-(phenylethynyl)-1,1'-biphenyl 
• 2920-38-9 4-cyano-1,1'-biphenyl 
• 1361950-30-2 [1,1′-biphenyl]-4-yl(p-tolyl)sulfane 
• 2950-30-3 2-([1,1’-biphenyl]-4-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol 
• 2369-31-5 1‐{[1,1'‐biphenyl]‐4‐yl}‐2,2,2‐trifluoroethanone 
• 5123-05-7 2-([1,1'-biphenyl]-4-yl)-5,5-dimethyl-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

CsF-Catalyzed Fluoroacylation of Tetrafluoroethylene Using Acyl Fluorides for the Synthesis of Pentafluoroethyl Ketones

A catalytic method for the synthesis of pentafluoroethyl ketones has been developed. The cesium fluoride catalyst can be used to convert acyl fluorides into the pentafluoroethyl ketones under tetrafluoroethylene pressure without generating stoichiometric

Synthesis of ArCF2X and [18F]Ar-CF3via Cleavage of the Trifluoromethylsulfonyl Group

A versatile synthesis of ArCF2X and [18F]Ar-CF3 type compounds from readily available ArCF2SO2CF3 has been developed. Diverse nucleophiles, including weak nucleophiles such as halides (18F-, Cl-, Br-, and I-), RSH, and ROH, could react with ArCF2SO2CF3 efficiently to give the corresponding difluoromethylene products. The control experiments and the Hammett plot indicated that the reaction might proceed through a difluorocarbocation intermediate generated from the steric hindrance-assisted cleavage of the trifluoromethylsulfonyl group.

Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles

A series of acyl fluorides was synthesized at 100 mmol scale using phase-transfer-catalyzed halogen exchange between acyl chlorides and aqueous bifluoride solution. The convenient procedure consists of vigorous stirring of the biphasic mixture at room temperature, followed by extraction and distillation. Isolated acyl fluorides (usually 7-20 g) display excellent purity and can be transformed into sterically hindered amides and esters when treated with lithium amide bases and alkoxides under mild conditions.

Rapid and column-free syntheses of acyl fluorides and peptides usingex situgenerated thionyl fluoride

Thionyl fluoride (SOF2) was first isolated in 1896, but there have been less than 10 subsequent reports of its use as a reagent for organic synthesis. This is partly due to a lack of facile, lab-scale methods for its generation. Herein we report a novel protocol for theex situgeneration of SOF2and subsequent demonstration of its ability to access both aliphatic and aromatic acyl fluorides in 55-98% isolated yields under mild conditions and short reaction times. We further demonstrate its aptitude in amino acid couplings, with a one-pot, column-free strategy that affords the corresponding dipeptides in 65-97% isolated yields with minimal to no epimerization. The broad scope allows for a wide range of protecting groups and both natural and unnatural amino acids. Finally, we demonstrated that this new method can be used in sequential liquid phase peptide synthesis (LPPS) to afford tri-, tetra-, penta-, and decapeptides in 14-88% yields without the need for column chromatography. We also demonstrated that this new method is amenable to solid phase peptide synthesis (SPPS), affording di- and pentapeptides in 80-98% yields.

Synthesis method of acyl fluoride

The invention belongs to the technical field of synthesis of organic compounds, and relates to a synthesis method of acyl fluoride. The invention relates to a synthesis method of acyl fluoride, which is characterized in that carboxylic acid trifluoromethy

Acyl fluorides from carboxylic acids, aldehydes, or alcohols under oxidative fluorination

We describe a novel reagent system to obtain acyl fluorides directly from three different functional group precursors: carboxylic acids, aldehydes, or alcohols. The transformation is achieved via a combination of trichloroisocyanuric acid and cesium fluoride, which facilitates the synthesis of various acyl fluorides in high yield (up to 99%). It can be applied to the late-stage functionalization of natural products and drug molecules that contain a carboxylic acid, an aldehyde, or an alcohol group.

Stoichiometric Studies on the Carbonylative Trifluoromethylation of Aryl Pd(II) Complexes using TMSCF3 as the Trifluoromethyl Source

We have performed a series of stoichiometric studies in order to identify viable steps for a hypothetical catalytic cycle for the palladium-mediated carbonylative coupling of an aryl bromide with TMSCF3. Our work revealed that benzoyl Pd(II) complexes bearing Xantphos or tBu3P as the phosphine ligands, which are generated from the corresponding PdII(Ph)Br complexes exposed to stoichiometric 13CO from 13COgen, were unable to undergo transmetalation and reductive elimination to trifluoroacetophenone. Instead, in the presence of base and additional CO, these organometallic complexes readily underwent reductive elimination to the acid fluoride. Attempts to determine whether the acid fluoride could represent an intermediate for acetophenone production were unrewarding. Only in the presence of a boronic ester did we observe some formation of the desired product, although the efficiency of transformation was still low. Finally, we investigated the reactivity of four phosphine-ligated PdII(Ph)CF3 complexes (Xantphos, DtBPF, tBu3P, and triphenylphosphine) with carbon monoxide. With the exception of the tBu3P-ligated complex, all other metal complexes led to the facile formation of trifluoroacetophenone. We also determined in the case of triphenylphosphine that CO insertion occurred into the Pd-Ar bond, as trapping of this complex with n-hexylamine led to the formation of n-hexylbenzamide.

Synthesis of Arylstannanes via Palladium-Catalyzed Decarbonylative Coupling of Aroyl Fluorides

Aryl stannanes are valuable precursors in organic transformations, but their synthetic methods are limited. Here we present a Pd-catalyzed decarbonylative stannylation of acid fluorides in the absence of exogenous base. Various aryl stannanes were efficiently prepared from bench-stable transition metal catalyst and ligand with broad functional group compatibility and substrate scope including natural products and pharmaceuticals. This protocol was also successfully used to a late-stage diversification of an existing uricosuric drug probenecid. (Figure presented.).

Methoxylation of Acyl Fluorides with Tris(2,4,6-trimethoxyphenyl)phosphine via C-OMe Bond Cleavage under Metal-Free Conditions

Acyl fluorides are subjected to methoxylation with tris(2,4,6-trimethoxyphenyl)phosphine (TMPP) to afford the corresponding methyl esters in good to excellent yields. This transformation is featured by C(sp2)-OMe bond cleavage under metal-free conditions. Unprecedented utilization of TMPP as a methoxylating agent realized the installation of an OMe group into the desired products.