27730-00-3

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 98-86-2 acetophenone 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 100-52-7 benzaldehyde 
• 4636-16-2 iodoacetophenone 
• 532-27-4 1-chloroacetophenone 
• 1774-66-9 3-(4-bromophenyl)-1-phenylprop-2-en-1-one 
• 70-11-1 α-bromoacetophenone 
• 100-42-5 styrene 
• 22966-09-2 (2E)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one 

Downstream Products

• 1438287-42-3 4-(4-bromobenzyl)-2-(4-chlorophenyl)-4-phenyl-4H-imidazol-5-ol 
• 1438287-52-5 4-(4-bromobenzyl)-2,4-diphenyl-4H-imidazol-5-ol 
• 1438287-60-5 4-(4-bromobenzyl)-4-phenyl-2-(pyridin-3-yl)-4H-imidazol-5-ol 
• 128126-18-1 trans-(2S,3R)-2,3-epoxy-3-phenyl-1-(4-bromophenyl)-1-propan-1-one 
• 106002-84-0 3-(4-bromophenyl)-1-phenylpropane-1,2-dione 
• 106002-79-3 erythro-N-(2-benzoyl-1-p-bromophenyl-2-chloroethyl)-S-methyl thiocarbamate 
• 106002-81-7 erythro-N-(2-benzoyl-1-p-bromophenyl-2-chloroethyl)-S-isopropyl thiocarbamate 
• 106002-80-6 erythro-N-(2-benzoyl-1-p-bromophenyl-2-chloroethyl)-S-ethyl thiocarbamate 
• 99430-37-2 3-(4-Bromo-phenyl)-3-fluoro-2-hydroxy-1-phenyl-propan-1-one 
• 135460-29-6 3-Bromo-3-(4-bromo-phenyl)-2-hydroxy-1-phenyl-propan-1-one 

Relevant academic research and scientific papers

Asymmetric Epoxidation of Enones Promoted by Dinuclear Magnesium Catalyst

Asymmetric synthesis with cheaper and non-toxic alkaline earth metal catalysts is becoming an important and sustainable alternative to conventional catalytic methodologies mostly relying on precious metals. In spite of some sustainable methods for enantioselective epoxidation of enones, the development of a well-defined and efficient catalyst based on magnesium complexes for these reactions is still a challenging task. In this perspective, we present the application of chiral dinuclear magnesium complexes for asymmetric epoxidation of a broad range of electron-deficient enones. We demonstrate that the in situ generated magnesium-ProPhenol complex affords enantioenriched oxiranes in high yields and with excellent enantioselectivities (up to 99% ee). Our extensive study verifies the literature data in this area and provides a step forward to better understand the factors controlling the oxygenation process. Elaborated catalyst offers mild reaction conditions and a truly wide substrate scope. (Figure presented.).

Synthesis and characterization of 1,3,5-triarylpyrazol-4-ols and 3,5-diarylisoxazol-4-ols from chalcones and theoretical studies of the stability of pyrazol-4-ol toward acid dehydration

The synthesis of diverse pyrazol-4-ol and isoxazole-4-ol heterocycles involving only 3 reaction steps is reported in this study. However, the synthesis of carboxamide pyrazol-4-ol has failed in the conditions used in the synthesis, acid methanol solution. The carboxamide pyrazol-4-ol decomposes via dehydration, forming the respective pyrazol. Theoretical calculations were used to elucidate the dehydration reaction. We have found a mechanism for acid-catalyzed dehydration that can explain the experimental observations. The calculated free energy profile for acid-catalyzed dehydration of the carboxamide pyrazol-4-ol and phenylpyrazole-4-ol point out that the latter is more stable in relation dehydration, with a dehydration rate 100 times smaller in acid methanol solution.

Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts

A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.

Pyrenediones as versatile photocatalysts for oxygenation reactions with: In situ generation of hydrogen peroxide under visible light

Pyrenediones (PYDs) are efficient photocatalysts for three oxygenation reactions: Epoxidation of electron deficient olefins, oxidative hydroxylation of organoborons, and oxidation of sulfides via in situ generation of H2O2 under visible light irradiation, using oxygen as a terminal oxidant and IPA as a solvent and a hydrogen donor.

Organocatalytic Enantioselective γ-Elimination: Applications in the Preparation of Chiral Peroxides and Epoxides

An organocatalyzed enantioselective γ-elimination process has been achieved and applied in the kinetic resolution of peroxides to access chiral peroxides and epoxides. The reaction provided a pathway for the preparation of two useful synthetic and biologically important structural motifs through a single-step reaction. A range of substrates has been resolved with a selectivity factor up to 63. The obtained enantioenriched peroxides and epoxides allowed a series of transformations with retained optical purities.

Application of chiral TADDOL ligand and rare earth metal amide in combined catalysis of asymmetric reaction

The invention relates to application of chiral TADDOL ligand and rare earth metal amide in combined catalysis of asymmetric epoxidation reaction of chalcone compounds. According to the application, alpha, beta-unsaturated ketone shown in a formula (1) and tert-butyl hydroperoxide react in the presence of organic alkali under the combined catalytic action of a chiral TADDOL ligand shown in a formula (3) and rare earth metal amide in an anhydrous, oxygen-free and protective atmosphere to obtain the chiral epoxy compound shown in the formula (2) after the reaction is completed, wherein R1 is selected from hydrogen, alkyl, halogen, alkoxy, trifluoromethyl, nitro or cyano, R2 is selected from phenyl, substituted phenyl, naphthyl, furyl or thienyl; R3 and R4 are respectively and independently selected from alkyl, phenyl or R3 and R4 and carbon atoms connected with R3 and R4 form naphthenic base; Ar is phenyl, substituted phenyl, biphenyl or naphthyl; the molecular formula of the rare earth metal amide is RE [N (SiMe3) 2] 3. The method has the advantages of wide substrate application range, high yield and high enantioselectivity.

Quest for Efficient Catalysts based on Zinc tert-Butyl Peroxides for Asymmetric Epoxidation of Enones: C2- vs C1-Symmetric Auxiliaries

Zinc tert-butyl peroxide-based catalysts for the asymmetric epoxidation of enones using tert-butyl hydroperoxide as an oxidant have been developed. A comparative study of chiral monoanioninc N,N′-bidentate ligands, C2-symmetric bisoxazolinates and C1-symmetric enaminooxazolinates, revealed excellent performance of C1-symmetric auxiliary ligands on catalytic asymmetric epoxidation of enones (up to 96% yield, 91% ee).

One-Pot Aerobic Photooxidative Darzens Reaction from Styrene and Benzyl Alcohol via Phenacyl Iodide and Benzaldehyde by Using?- Iodine

We report a one-pot protocol for the synthesis of α,β-epoxy ketones from benzyl alcohols and styrenes with molecular oxygen, visible light, and molecular iodine. This procedure involves simultaneous aerobic photooxidative transformation of a benzyl alcohol into a benzaldehyde and of a styrene into a phenacyl iodide, with a subsequent Darzens reaction in one pot. This is the first report of a one-pot oxidative Darzens reaction starting from benzyl alcohols and styrenes.

N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Alkenes/ α-Bromoacetophenones with Aldehydes: A Facile Entry to α,β-Epoxy Ketones

A novel, N-heterocyclic carbene (NHC) catalyzed direct oxidative coupling of styrenes with aldehydes has been described for the synthesis of α,β-epoxy ketones in good yields. This unprecedented regioselective oxidative coupling employs NBS/DBU/DMSO (DBU=1,8-diazabicyclo [5.4. 0] undec-7-ene, DMSO=dimethylsulfoxide, NBS=N-bromosuccinimide) as an oxidative system at ambient conditions. Additionally, first NHC-catalyzed Darzens reaction of α-bromoketones and aldehydes under mild reaction conditions has also been described. Interestingly, mechanistic studies have revealed the preferred reactivity of NHC with alkene/α-bromoketone rather than aldehydes, thus proceeding via the ketodeoxy Breslow intermediate.

Preparation of mesoporous zeolite ETS-10 catalysts for high-yield synthesis of α,β-epoxy ketones

Developing highly active heterogeneous catalysts for the efficient construction of valuable building blocks is of great importance to synthetic chemistry. For this purpose, a mesoporous zeolite ETS-10 (METS-10) is synthesized by using a mesoscale silane surfactant as a template and applied to achieve highly efficient syntheses of α,β-epoxy ketones by employing simple alkenes and aldehydes as starting materials. The high activity of the METS-10 catalyst is attributed to its unique porous structure and basicity. Electron paramagnetic resonance characterization results and theoretical calculation experimental data reveal that the strong basic sites on METS-10 catalyst can activate the reaction substrate and intermediate. In addition, the mesopores in METS-10 catalyst benefit the mass transfer and further improve the catalytic activity. Mesoporous zeolite ETS-10 is synthesized by using mesoscale silane surfactant as a template and applied to the highly efficient synthesis of α,β-epoxy ketones by employing simple alkenes and aldehydes as starting materials. The high activity of the mesoporous ETS-10 catalyst is attributed to its unique porous structure and basicity.