40794-87-4

Upstream product

• 21053-98-5 5-(4-methylphenyl)-3H-furan-2-one 
• 71-43-2 benzene 
• 37032-34-1 2-fluoro-1-(4-methylphenyl)ethanone 
• 98-86-2 acetophenone 
• 450-95-3 2-fluoroacetophenone 
• 122-00-9 para-methylacetophenone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 874-60-2 4-methyl-benzoyl chloride 
• 768-03-6 Phenyl vinyl ketone 
• 74032-45-4 S-2-pyridyl 4-methylbenzothiolate 
• 70-11-1 α-bromoacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 583-06-2 3-benzoylacrylic acid 
• 104-87-0 4-methyl-benzaldehyde 

Downstream Products

• 21399-31-5 2-(4-methylphenyl)-5-phenyl-1H-pyrrole 
• 119492-83-0 2-(4-Methoxyphenyl)-5-phenylfuran 
• 1014981-35-1 C₁₉H₁₇NO₂ 
• 23460-45-9 Z,Z-1-(p-Tolyl)-4-phenyl-1,4-bis-(ethylmercapto)-buta-1,3-dien 

Relevant academic research and scientific papers

Asymmetric hydrogenation of 1,4-diketones: facile synthesis of enantiopure 1,4-diarylbutane-1,4-diols

Owing to the biological significance and great synthetic value of 1,4-diarylbutane-1,4-diols and their derivatives, increasingly considerable attention has been paid to developing effective synthetic methods for chiral 1,4-diarylbutane-1,4-diols. We herei

Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions

Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.

Proton-Coupled Electron Transfer: Transition-Metal-Free Selective Reduction of Chalcones and Alkynes Using Xanthate/Formic Acid

Highly chemoselective reduction of α,β-unsaturated ketones to saturated ketones and stereoselective reduction of alkynes to (E)-alkenes has been developed under a transition-metal-free condition using a xanthate/formic acid mixture through proton-coupled electron transfer (PCET). Mechanistic experiments and DFT calculations support the possibility of a concerted proton electron-transfer (CPET) pathway. This Birch-type reduction demonstrates that a small nucleophilic organic molecule can be used as a single electron-transfer (SET) reducing agent with a proper proton source.

Detrifluoroacetylation Reaction of Trifluoromethyl-β-diketones: Facile Method for the Synthesis of Succinimide Derivatives and 1,4-Diketones

Currently, a great deal of research efforts are focused on C–C bond activation for development of novel synthetic methodology. In this paper, a detrifluoroacetylation of trifluoromethyl-β-diketones is described, which allows for the synthesis of succinimides and 1,4-diketones through cascade Michael addition/retro-Claisen reaction and nucleophilic substitution/retro-Claisen reaction. The readily available trifluoromethyl-β-diketones, wide substrate scope, and mild conditions make this method very practical.

Light-Driven Vitamin B12-Catalysed Generation of Acyl Radicals from 2-S-Pyridyl Thioesters

Acyl radicals are invaluable intermediates in organic synthesis, however their generation remains challenging. Herein, we present an unprecedented light-driven, cobalt-catalysed method for the generation of acyl radicals from readily available 2-S-pyridyl thioesters. The synthetic potential of this methodology was demonstrated in the Giese-type acylation of activated olefins in the presence of heptamethyl cobyrrinate. This vitamin B12 derivative proved to be the most efficient catalyst in the studied process. The developed method features broad substrate scope (38 examples), good functional group tolerance, and mild reaction conditions. Moreover, it is easily scalable (illustrated on a 20-fold scale-up procedure), enabling its preparative use. Mechanistic studies revealed that the reaction proceeds via a radical pathway with the key steps involving the formation of an acyl-vitamin B12 complex and subsequent photolysis of the Co?C bond. (Figure presented.).

Tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester in water: An efficient and sustainable synthesis of 1,3,4′-tricarbonyl compounds

An efficient and sustainable synthesis of the otherwise difficult to obtain 1,3,4′-tricarbonyl compounds through a water mediated, TBAF·3H2O promoted unprecedented tandem reaction of 1,2-allenic ketone with α-halo ketone or α-halo ester has been developed. Remarkably enhanced reactivity and improved chemoselectivity by using water as the reaction medium was observed. The 1,3,4′-tricarbonyl compounds facilitate further versatile transformations, which underscores the importance of these products as synthetic intermediates. The Royal Society of Chemistry.

Synthesis of water-tolerant indium homoenolate in aqueous media and its application in the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling with acid chloride

The first water-tolerant, ketone-type indium homoenolate was synthesized via the oxidative addition of In/InCl3 to enones. The reaction proceeds exclusively in aqueous media. Both indium and indium(III) chloride are necessary for the smooth conversion of the reaction. Similar results were obtained when InCl or InCl2 was used in place of In/InCl3. The synthetic utility of the indium homoenolate was demonstrated through the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling of indium homoenolate with acid chloride.

Carbonylative 1,4-addition of potassium aryltrifluoroborates to vinyl ketones

Potassium aryltrifluoroborates have proven to be useful reagents for the carbonylative aroylation of vinyl ketones; this study broadens the scope of potassium aryltrifluoroborates in homogeneous catalysis and shows that the solvent can act as the proton s

Acylguanidine inhibitors of β-secretase: Optimization of the pyrrole ring substituents extending into the S1 and S3 substrate binding pockets

Proteolytic cleavage of amyloid precursor protein by β-secretase (BACE-1) and γ-secretase leads to formation of β-amyloid (Aβ) a key component of amyloid plaques, which are considered the hallmark of Alzheimer's disease. Small molecule inhibitors of BACE-1 may reduce levels of Aβ and thus have therapeutic potential for treating Alzheimer's disease. We recently reported the identification of a novel small molecule BACE-1 inhibitor N-[2-(2,5-diphenyl-pyrrol-1-yl)-acetyl]guanidine (3.a.1). We report here the initial hit-to-lead optimization of this hit and the SAR around the aryl groups occupying the S1 and S2′ pockets leading to submicromolar BACE-1 inhibitors.

Cross-coupling reaction of α-chloroketones and organotin enolates catalyzed by zinc halides for synthesis of γ-diketones

The reaction of tin enolates 1 with α-chloro- or bromoketones 2 gave γ-diketones (1,4-diketones) 3 catalyzed by zinc halides. In contrast to the exclusive formation of 1,4-diketones 3 under catalytic conditions, uncatalyzed reaction of 1 with 2 gave aldol-type products 4 through carbonyl attack. NMR study indicates that the catalyzed reaction includes precondensation between tin enolates and α-haloketones providing an aldol-type species and their rearrangement of the oxoalkyl group with leaving halogen to produce 1,4-diketones. The catalyst, zinc halides, plays an important role in each step. The carbonyl attack for precondensation is accelerated by the catalyst as Lewis acid and the intermediate zincate promotes the rearrangement by releasing oxygen and bonding with halogen. Various types of tin enolates and α-chloro and bromoketones were applied to the zinc-catalyzed cross-coupling. On the other hand, the allylic halides, which have no carbonyl moiety, were inert to the zinc-catalyzed coupling with tin enolates. The copper halides showed high catalytic activity for the coupling between tin enolates 1 and organic halides 7 to give γ,δ-unsaturated ketones 8 and/or 9. The reaction with even chlorides proceeded effectively by the catalytic system.