86109-33-3

Upstream product

• 10342-83-3 4'-Bromopropiophenone 
• 616-38-6 carbonic acid dimethyl ester 
• 251320-24-8 2-[(4-bromo-phenyl)-hydroxy-methyl]-acrylic acid methyl ester 
• 1122-91-4 4-bromo-benzaldehyde 
• 614-45-9 tert-Butyl peroxybenzoate 
• 126629-81-0 methyl 3-(4-bromophenyl)-3-oxopropanoate 
• 74-88-4 methyl iodide 
• 292638-85-8 acrylic acid methyl ester 
• 586-75-4 4-chlorobenzoyl chloride 
• 34757-14-7 methyl 2-diazopropanoate 
• 201230-82-2 carbon monoxide 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 1443454-33-8 methyl 2-azido-3-(4-bromophenyl)-2-methyl-3-oxopropanoate 

Relevant academic research and scientific papers

Palladium Catalyzed Ring Expansion Reaction of Isoxazolones with Isocyanides: Synthesis of 1,3-Oxazin-6-One Derivatives

A palladium catalyzed ring expansion reaction of isoxazolones with isocyanides was disclosed. In the reaction, a cascade process involving ring-opening/cyclization was suggested. The reaction features high atomic economy due to no elimination of CO2 occurred. Moreover, products obtained demonstrate aggregation-induced emission properties with relatively high solid-state emission efficiencies. (Figure presented.).

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.

Morita-Baylis-Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI-MS(/MS)

Abstract We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to goo

Tert -butyl peroxybenzoate-promoted α-methylation of 1,3-dicarbonyl compounds

A tert-butyl peroxybenzoate (TBPB)-promoted direct α-methylation of 1,3-dicarbonyl compounds has been developed, providing α-methyl derivatives in moderate to good yields. In this procedure, TBPB plays a dual role, serving as both the methyl source and radical initiator. This work represents a key complement to the traditional α-methylation of 1,3-dicarbonyl compounds using methyl iodide.

Regio-and enantioselective bioreduction of methyleneketoesters using both polymeric resin and cellulose matrix

Methyleneketoesters were prepared in >90% yield by performing an IBX oxidation of Morita-Baylis-Hillman adducts. A methodology was developed to achieve methyl 3-aryl-3-keto-2-methylenepropanoate reduction using a screening of yeast strains in three different reaction procedures to obtain products with both high yield and diastereoselectivity. The reactions conducted in water provided inferior yields (50%) for substrates 2b-c. Employing Amberlite XAD7HP which was a substrate reservoir that also immediately extracted the products from the reaction medium after their formation, syn-4a-c and anti-4a-c were isolated in 60-70% yield, with high stereoselectivity (98-99% ee). The best results were obtained using substrates adsorbed on filter paper which provided products yields above 70%, a 99% ee and a diastereomoeric ratio (syn-4: anti-4) 9:1. Cellulose matrix has excellent potential to be successfully employed in general biocatalytic reactions.

Azidation of β-keto esters and silyl enol ethers with a benziodoxole reagent

The efficient azidation of β-keto esters and silyl enol ethers using a benziodoxole-derived azide transfer reagent is reported. The azidation of cyclic β-keto esters could be achieved in up to quantitative yields in the absence of any catalyst. In the case of less reactive linear β-keto esters and silyl enol ethers, complete conversion and good yields could be obtained by using a zinc catalyst.

Rhodium-catalyzed hydroaroylation of α,β-unsaturated esters using aroyl chlorides and Et2MeSiH

Hydroaroylation of methyl acrylate 2a to give the α-aroyl esters 4 took place in the three-component reaction of 2a, aroyl chlorides 1, and Et 2MeSiH in the presence of 1 mol % of [Rh(cod)(PR3) 2]OTf (cod = 1,5-cyclooctadi

Palladium-catalyzed carbonylation/acyl migratory insertion sequence

Chemical Equation Presented On the move: A palladium-catalyzed reaction of aryl iodides, diazo compounds or N-tosylhyd razones, and carbon monoxide affords β-oxo esters or ketones/ enones (see scheme; DCE = l,2-dichloroethane). The products are delivered with high efficiency through the title sequence.