149104-90-5

Usage

Uses

Used in Chemical Synthesis:
4-Acetylphenylboronic acid is used as a reactant in several chemical reactions for the synthesis of complex organic molecules. Its ability to participate in cross-coupling reactions makes it a valuable compound in the field of organic chemistry.
Used in Suzuki Reaction:
In the field of chemical synthesis, 4-Acetylphenylboronic acid is used as a reactant in the Suzuki reaction, a widely employed palladium-catalyzed cross-coupling reaction that forms carbon-carbon bonds between an organoboronic acid and an organic halide or triflate.
Used in Palladium-catalyzed Decarboxylative Coupling:
4-Acetylphenylboronic acid is used as a reactant in palladium-catalyzed decarboxylative coupling, a reaction that involves the coupling of an organoboronic acid with a carboxylic acid, leading to the formation of a carbon-carbon bond and the release of carbon dioxide.
Used in Copper-catalyzed Hydroxylation:
4-Acetylphenylboronic acid is used as a reactant in copper-catalyzed hydroxylation, a reaction that introduces a hydroxyl group to an organic molecule, often resulting in the formation of alcohols or phenols.
Used in Palladium-catalyzed Suzuki-Miyaura Cross-coupling:
In the field of chemical synthesis, 4-Acetylphenylboronic acid is used as a reactant in palladium-catalyzed Suzuki-Miyaura cross-coupling, a reaction that forms carbon-carbon bonds between an organoboronic acid and an organic halide or triflate, facilitating the synthesis of complex organic molecules.
Used in Cross-coupling with α-Bromocarbonyl Compounds:
4-Acetylphenylboronic acid is used as a reactant in cross-coupling reactions with α-bromocarbonyl compounds, a process that involves the formation of carbon-carbon bonds and is essential for the synthesis of various organic compounds.
Used in Oxidation Catalyzed by Baeyer-Villiger Monooxygenases:
4-Acetylphenylboronic acid is used as a reactant in oxidation reactions catalyzed by Baeyer-Villiger monooxygenases, an enzyme class that catalyzes the oxidation of ketones to esters, providing a valuable synthetic route for the preparation of various organic compounds.
Used in 1,5-Substitution Reactions:
4-Acetylphenylboronic acid is used as a reactant in 1,5-substitution reactions, a type of organic reaction that involves the replacement of a functional group at the 1st and 5th positions of a molecule, leading to the formation of new organic compounds.
Used in Dendrimers Synthesis:
4-Acetylphenylboronic acid is used as a reactant in the synthesis of dendrimers, highly branched macromolecules with a well-defined structure, which have applications in various fields, including drug delivery, catalysis, and nanotechnology. It undergoes Suzuki coupling with 4-bromotriphenylamine catalyzed by dichlorobis(triphenylphosphine)Pd(II) during the synthesis process.

InChI:InChI=1/C8H9BO3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5,11-12H,1H3

Upstream product

• 518336-20-4 (4-(1-hydroxyethyl)phenyl)boronic acid 
• 13675-18-8 tetrahydroxydiboron 
• 13329-40-3 4-Iodoacetophenone 
• 109613-00-5 4-acetophenyl triflate 
• 99-90-1 para-bromoacetophenone 
• 2156-04-9 4-Vinylphenylboronic acid 
• 1173922-30-9 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanol 
• 171364-81-1 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone 
• 99-92-3 p-aminobenzophenone 
• 350-47-0 1-(4-acetylphenyl)diazonium tetrafluoroborate 
• 61390-40-7 1-bromo-4-(1,1-diethoxyethyl)benzene 

Downstream Products

• 13021-18-6 1-(4'-methoxy-biphenyl-4-yl)-ethanone 
• 56917-39-6 4-acetyl-2'-methylbiphenyl 
• 787-69-9 4,4'-diacetylbiphenyl 
• 94705-09-6 (4-acetylphenyl)(phenyl)methanol 
• 215876-83-8 2-(4-acetylphenyl)-4,5-dimethyl-1,3,2-dioxaborolane 
• 1528-42-3 ethyl 4-acetylphenylacetate 
• 173464-57-8 (E)-3-(4-acetylphenyl)acrylic acid butyl ester 
• 1009-61-6 1,4-Diacetylbenzene 
• 53689-84-2 4-acetylbenzophenone 
• 23600-83-1 1-(4-(phenylamino)phenyl)ethanone 
• 20488-43-1 4-acetyl-trans-stilbene 

Relevant academic research and scientific papers

Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source

In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- And Rhodium-Catalyzed Sequential Relay Reactions

Asymmetric conjugate addition of aryl halides or aryl triflates to electron-deficient olefins was realized by sequential Miyaura borylation and Hayashi-Miyaura conjugate addition in one pot. A nickel-catalyzed borylation of aryl halides or triflates and a rhodium-chiral diene complex catalyzed enantioselective conjugate addition was executed as a pair of relay reactions as a more efficient and greener protocol.

Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water

A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 h in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.

Development of a Concise Multikilogram Synthesis of LPA-1 Antagonist BMS-986020 via a Tandem Borylation-Suzuki Procedure

The process development for the synthesis of BMS-986020 (1) via a palladium catalyzed tandem borylation/Suzuki reaction is described. Evaluation of conditions culminated in an efficient borylation procedure using tetrahydroxydiboron followed by a tandem Suzuki reaction employing the same commercially available palladium catalyst for both steps. This methodology addressed shortcomings of early synthetic routes and was ultimately used for the multikilogram scale synthesis of the active pharmaceutical ingredient 1. Further evaluation of the borylation reaction showed useful reactivity with a range of substituted aryl bromides and iodides as coupling partners. These findings represent a practical, efficient, mild, and scalable method for borylation.

Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules

A practical and general iron-catalyzed Wacker-type oxidation of olefins to ketones is presented, and it uses ambient air as the sole oxidant. The mild oxidation conditions enable exceptional functional-group tolerance, which has not been demonstrated for any other Wacker-type reaction to date. The inexpensive and nontoxic reagents [iron(II) chloride, polymethylhydrosiloxane, and air] can, therefore, also be employed to oxidize complex natural-product-derived and polyfunctionalized molecules.

Method forsynthesizing ketone by oxidation of alkene under catalysis of iron

The invention discloses a method for synthesizing ketoneby oxidation of alkene under catalysis of iron, and belongs to the field of catalyzed synthesis technologies and fine chemical synthesis. According to the specific method, air or oxygen is taken as an oxidizing agent under the acceleration action ofhydrosilaneand a ketone compound is synthesized byoxidation of alkene under catalysis of iron. The method has the advantages that the catalyst is wide in source, cheap and environment-friendly; the oxidant is wide in source and cheap and does not generate a waste; the reaction conditions are mild, the selectivity is high and the yield is high;a substrate is wide and stable; a functional group of the substrate is good in compatibility and the application range of the substrate is wide; and alkene molecules can be well converted into the ketone. The separation yield of a target product reaches 98% under the optimized reaction conditions.

Visible-Light Photoredox Borylation of Aryl Halides and Subsequent Aerobic Oxidative Hydroxylation

Efficient and practical visible-light photoredox borylation of aryl halides and subsequent aerobic oxidative hydroxylation were developed. The protocols use readily available aryl halides and bis(pinacolato)diboron as the starting materials, fac-Ir(ppy)3 as the photocatalyst, and corresponding arylboronic esters and phenols were obtained in good yields. The methods show some advantages including simple equipment, mild conditions, easy operation, and wide substrate scope. Therefore, they should provide a valuable strategy for chemical transformations.

Application of a promiscuous Arthrobacter sp. from Antarctic in aerobic (R)-selective deracemization and anaerobic (S)-selective reduction

Inspired by enzyme-catalyzed reactions with microorganisms found in harsh marine environments, in which the amount of oxygen is restrict, we have shown that Arthrobacter sp. can perform different chemical transformations by switching from anaerobic to aerobic reaction conditions. Depending on the presence or absence of oxygen, either alcohol deracemization or ketone reduction with enantiocomplementary selectivities can be performed by the same microorganism. For example, reactions performed in the presence of oxygen favored the deracemization process, in which a racemic mixture of 1-(4-methylphenyl)ethanol was enriched to the (R)-alcohol in high conversion (94%) and high enantiomeric excess (94%). On the other hand, reaction in the absence of oxygen favored the reduction process, in which 4-methyl-acetophenone was converted to the (S)-alcohol in good conversion (58%) and excellent enantiomeric excess (>99%). These concepts were applied for both deracemization and enantioselective reduction of heteroatom-containing (silicon, phosphorus, tin and boron) molecules. Moreover, preparative scale reactions were also performed for both chemical processes.

An easy route to (hetero)arylboronic acids

An unprecedented spontaneous reactivity between diazonium salts and diboronic acid has been unveiled, leading to a versatile arylboronic acid synthesis directly from (hetero)arylamines. This fast reaction (35 min overall) tolerates a wide range of functional groups and is carried out under very mild conditions. The radical nature of the reaction mechanism has been investigated.

Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]

Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.