4441-01-4

Usage

Uses

Used in Organic Synthesis:
1,2,4-TRIPHENYL-1,4-BUTANEDIONE is used as a building block for the synthesis of various organic compounds due to its reactivity and structural properties.
Used in Pharmaceutical Production:
1,2,4-TRIPHENYL-1,4-BUTANEDIONE is used as a precursor in the production of pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Agrochemical Production:
1,2,4-TRIPHENYL-1,4-BUTANEDIONE is used as a precursor in the production of agrochemicals, aiding in the creation of effective crop protection agents.
Used in the Polymer Industry:
1,2,4-TRIPHENYL-1,4-BUTANEDIONE is used as a photoinitiator, playing a crucial role in the polymerization process and the manufacturing of various polymer products.
Used in Sunscreen Products:
1,2,4-TRIPHENYL-1,4-BUTANEDIONE is used as a UV-absorber in sunscreens, providing protection against harmful ultraviolet radiation.
Used in Fluorescent Dyes Preparation:
1,2,4-TRIPHENYL-1,4-BUTANEDIONE is used as a reagent in the preparation of fluorescent dyes, contributing to the development of specialized dyes for various applications.
Used in Catalysts for Organic Synthesis:
1,2,4-TRIPHENYL-1,4-BUTANEDIONE is used as a catalyst in the synthesis of various organic compounds, enhancing the efficiency and selectivity of chemical reactions.

InChI:InChI=1/C22H18O2/c23-21(18-12-6-2-7-13-18)16-20(17-10-4-1-5-11-17)22(24)19-14-8-3-9-15-19/h1-15,20H,16H2/t20-/m1/s1

Upstream product

• 108-31-6 maleic anhydride 
• 60-29-7 diethyl ether 
• 1074-12-0 phenylglyoxal hydrate 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 151-50-8 potassium cyanide 
• 98-86-2 acetophenone 
• 22563-99-1 3-dimethylamino-1,2-diphenyl-propan-1-one 
• 100-52-7 benzaldehyde 
• 94-41-7 benzalacetophenone 
• 2901-80-6 N-benzoyl-D,L-valine 
• 15345-47-8 1,2,3,5-tetraphenyl-pyrrole 
• 103166-34-3 1-benzyl-2,3,5-triphenyl-1H-pyrrole 
• 54282-53-0 deoxybenzoin enolate 
• 28531-58-0 (2-oxo-2-phenylethyl)mercury chloride 

Downstream Products

• 102662-06-6 3-chloro-2,4,5-triphenyl-furan 
• 3274-61-1 2,4,5-triphenylpyrrole 
• 15345-47-8 1,2,3,5-tetraphenyl-pyrrole 
• 102882-80-4 1-allyl-2,3,5-triphenyl-pyrrole 
• 135347-54-5 1,2,5-Trihydroxy-1-oxo-2,3,5-triphenylphospholane 
• 135347-67-0 1,4-Dihydroxy-1,2,4-triphenyl-1,4-butane-diphosphonous acid 
• 20851-07-4 2,3,5-triphenylthiophene 
• 95162-24-6 3-bromo-1,2,4-triphenyl-butane-1,4-dione 
• 53751-25-0 3-bromo-2,4,5-triphenylfuran 
• 6707-63-7 3-benzoyl-4,5-diphenylisoxazole 
• 65-85-0 benzoic acid 
• 2272-58-4 3,4,6-triphenyl-pyridazine 
• 5435-97-2 1-phenyl-1,2-dibenzoylethylene 
• 103166-35-4 2,3,5-triphenyl-1-(p-tolyl)-1H-pyrrole 

Relevant academic research and scientific papers

N-Heterocyclic Carbene-Photocatalyzed Tricomponent Regioselective 1,2-Diacylation of Alkenes Illuminates the Mechanistic Details of the Electron Donor-Acceptor Complex-Mediated Radical Relay Processes

Progress in the development of photocatalytic reactions requires a detailed understanding of the mechanisms underpinning the observed reactivity, yet mechanistic details of many photocatalytic systems, especially those that involve electron donor-acceptor complexes, have remained elusive. We report herein the development and a combined mechanistic and computational study of photocatalytic alkene 1,2-diacylation that enables a regioselective installation of two different acyl groups, establishing direct, tricomponent access to 1,4-diketones, key intermediates in heterocyclic and medicinal chemistry. The studies revealed the central role of the electron donor-acceptor complex formed from an N-heterocyclic carbene (NHC) catalyst-derived intermediate and an acyl transfer reagent, providing a detailed description of the structural and electronic factors determining the characteristics of the photoinduced charge-transfer process that mediates photocatalytic transformation. The in-depth investigation also illuminated the roles of other radical intermediates and electron donors relevant to the catalytic activities of N-heterocyclic carbenes in radical reactions.

Photoredox-Enabled Chromium-Catalyzed Alkene Diacylations

Transition-metal-catalyzed cross-coupling reactions are a powerful tool to construct carbon-carbon bonds in modern synthetic chemistry. Chromium catalysis is much less developed compared with the widely used palladium and nickel catalysis. Herein, we repo

Direct 1,2-Dicarbonylation of Alkenes towards 1,4-Diketones via Photocatalysis

1,4-Dicarbonyl compounds are intriguing motifs and versatile precursors in numerous pharmaceutical molecules and bioactive natural compounds. Direct incorporation of two carbonyl groups into a double bond at both ends is straightforward, but also challenging. Represented herein is the first example of 1,2-dicarbonylation of alkenes by photocatalysis. Key to success is that N(n-Bu)4+ not only associates with the alkyl anion to avoid protonation, but also activates the α-keto acid to undergo electrophilic addition. The α-keto acid is employed both for acyl generation and electrophilic addition. By tuning the reductive and electrophilic ability of the acyl precursor, unsymmetric 1,4-dicarbonylation is achieved for the first time. This metal-free, redox-neutral and regioselective 1,2-dicarbonylation of alkenes is executed by a photocatalyst for versatile substrates under extremely mild conditions and shows great potential in biomolecular and drug molecular derivatization.

Bio-inspired NHC-organocatalyzed Stetter reaction in aqueous conditions

The first bio-inspired N-Heterocyclic Carbene (NHC)-catalyzed Stetter reaction in aqueous medium is reported with benzaldehyde and chalcone as model substrates. A screening of azolium salts as precatalysts revealed the remarkable efficiency of synthetic thiazolium salt 8 (up to 90% conversion in pure water at 75 °C). The reaction was successfully extended to various simple aldehyde substrates. The effect of temperature was also investigated in order to extend the reaction to lower temperature allowing a potential application to sensitive biomolecules. This study highlighted the influence of both solvent and temperature on the 1,4-diketone 3/benzoin 4 ratio. New precatalysts 26 and 27 were designed and synthesized to explore a possible compartmentalization of the reaction in aqueous conditions. Owing to the use of inexpensive metal-free N-Heterocyclic Carbene (NHC) as a bioinspired catalyst, we anticipate that this green strategy in aqueous conditions will be attractive for bioconjugation of many biomolecule-type aldehydes and enone derivatives. This journal is

N-Heterocyclic Carbene Acyl Anion Organocatalysis by Ball-Milling

The ability to conduct N-heterocyclic carbene-catalysed acyl anion chemistry under ball-milling conditions is reported for the first time. This process has been exemplified through applications to intermolecular-benzoin, intramolecular-benzoin, intermolecular-Stetter and intramolecular-Stetter reactions including asymmetric examples and demonstrates that this mode of mechanistically complex organocatalytic reaction can operate under solvent-minimised conditions.

Acyl radicals from α-keto acids using a carbonyl photocatalyst: Photoredox-catalyzed synthesis of ketones

Acyl radicals have been generated from α-keto acids using inexpensive and commercially available 2-chloro-thioxanthen-9-one as the photoredox catalyst under visible light illumination. These reactive species added to olefins or coupled with aryl halides via a bipyridylstabilized Ni(II) catalyst, enabling easy access to a diverse range of ketones. This reliable, atom-economical, and eco-friendly protocol is compatible with a wide range of functional groups.

Synthesis of 1,4-Dicarbonyl Compounds by Visible-Light-Mediated Cross-Coupling Reactions of α-Chlorocarbonyls and Enol Acetates

Herein, we report a protocol for visible-light-mediated radical coupling reactions of α-chloroketones and enol acetates to afford 1,4-dicarbonyl compounds, which are important precursors and intermediates in organic synthesis. The reaction involves photoredox-catalyzed activation of the α-chloroketone upon photoelectron transfer, carbon–chlorine bond cleavage, and coupling of the resulting radical with the carbon–carbon double bond of the enol acetate. This mild protocol has a wide substrate scope and moderate to good yields. (Figure presented.).

Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME

Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.

Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones

Due to their closely matched reactivity, the coupling of two dissimilar ketone enolates to form a 1,4-diketone remains a challenge in organic synthesis. We herein report that umpolung of a ketone trimethylsilyl enol ether (1 equiv) to form a discrete enol

Oxidative acylation of α,α-diarylallylic alcohols: Synthesis of 1,2,4-triarylbutane-1,4-diones

A metal-free mediated oxidative acylation of α,α-diarylallylic alcohols with simple aromatic aldehydes for the synthesis of 1,2,4-triphenylbutane-1,4-diones is presented. In the presence of TBPB (tert-butyl peroxybenzoate), desired products were obtained in good to excellent yields for 28 examples. This protocol features high regioselectivity, wide functional group tolerance and atom economy.