10557-22-9

Upstream product

• 1346260-57-8 (E)-2-(2,2-dimethylhydrazono)-1-(3-methoxyphenyl)-propan-1-one 
• 1346260-40-9 (E)-2-(methoxyimino)-1-(3-methoxyphenyl)propan-1-one 
• 25594-66-5 1-cyano-1-(m-methoxyphenyl)propan-2-one 
• 51594-60-6 1-(3-methoxyphenyl)prop-2-en-1-one 

Downstream Products

• 1221265-54-8 2-(3-methoxyphenyl)-3-methyl-5-(trifluoromethyl)quinoxaline 
• 1221265-55-9 3-(3-methoxyphenyl)-2-methyl-5-(trifluoromethyl)quinoxaline 

Relevant academic research and scientific papers

Difluorination of Furonaphthoquinones

An unprecedented difluorination reaction was developed based on the furonaphthoquinone skeleton of natural products tanshinones and their analogues. By using Selectfluor as the fluorinating source and H2O as the hydroxyl source, a wide range of unique polycyclic α,α-difluoro β,β-dihydroxyl para-quinone products were achieved with yields up to 90%. The mechanistic studies revealed that the reaction might undergo tandem multiple electrophilic and nucleophilic substitutions, as well as cleavages of C-O and C-C bonds. This approach not only provides a new method to synthesis of α,α-difluoro ketones, but also affords a series of unique chemotypes for biological activity screening.

Direct Umpolung Morita–Baylis–Hillman like α-Functionalization of Enones via Enolonium Species

Herein we report on the umpolung of Morita–Baylis–Hillman type intermediates and application to the α-functionalization of enone C?H bonds. This reaction gives direct access to α-chloro-enones, 1,2-diketones and α-tosyloxy-enones. The latter are important intermediates for cross-coupling reaction and, to the best of our knowledge, cannot be made in a single step from enones in any other way. The proposed mechanism is supported by spectroscopic studies. The key initial step involves conjugate attack of an amine (DABCO or pyridine), likely assisted by hypervalent iodine acting as a Lewis acid leading to formation of an electrophilic β-ammonium-enolonium species. Nucleophilic attack by acetate, tosylate, or chloride anion is followed by base induced elimination of the ammonium species to give the noted products. Hydrolysis of α-acetoxy-enones lead to formation of 1,2-diketones. The α-tosyl-enones participate in Negishi coupling reactions under standard conditions.

Facile and selective hydrogenolysis of β-O-4 linkages in lignin catalyzed by Pd-Ni bimetallic nanoparticles supported on ZrO2

The β-O-4 linkage in lignin can be selectively cleaved by Pd-Ni bimetallic nanoparticles supported on ZrO2 using hydrogen gas as the hydrogen donor under ambient pressure and neutral conditions. Conspicuous enhancement in activity is observed compared with single nickel and palladium catalysts based on the results of experiments and characterization. Moreover, hydrogenation of the produced phenols is tuned by adjusting the amount of NaBH4. The catalyst can be reused over ten times in the model reaction and over five times in the hydrogenolysis of lignin without an obvious change in activity and selectivity.

Synthesis of 1,2-diketones from β-keto nitriles via a protection-oxidative-decyanation-deprotection protocol

A variety of 1,2-diketones were prepared from -keto nitriles via a three-step protocol including the protection of the ketones with methoxyamine, oxidative decyanation, and microwave-assisted deprotection in the final step. This approach provides a novel and efficient access to a wide scope of symmetric and unsymmetric 1,2-diketones using molecular oxygen as the oxidant in the decyanation process. Georg Thieme Verlag Stuttgart - New York.