81187-87-3

Upstream product

• 106-39-8 bromochlorobenzene 
• 623-70-1 ethyl (E)-crotonate 
• 99-91-2 para-chloroacetophenone 
• 21133-98-2 ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate 

Relevant academic research and scientific papers

Palladated Kaiser oxime resin as precatalyst for the Heck reaction in organic and aqueous media

A particular Kaiser oxime resin derived palladacycle is an efficient precatalyst for the Heck reaction with aryl iodides and bromides in DMF and in aqueous solvents under relatively moderate temperatures (110 °C and 120 °C) and high TON up to 105. Poisoning studies indicate that this polymer acts as a precatalyst. The polymer has been reused after recycling with low to moderate leaching of Pd(0). Georg Thieme Verlag Stuttgart.

Mono- and β,β-double-heck reactions of α,β-unsaturated carbonyl compounds in aqueous media

Optimized reaction conditions for the mono- and β,β-diarylation of electron-deficient alkenes in aqueous media catalyzed either by a p-hydroxyacetophenone oxime-derived palladacycle or by palladium(II) acetate under phosphine-free conditions and in the presence of (dicyclohexyl)- methylamine as base are described. Regioselective monoarylation of unsubstituted and substituted α,β-unsaturated carbonyl compounds takes place with aryl iodides at 120 °C in water. Aqueous N,N-dimethylacetamide (DMA), tetra-n-butylammonium bromide (TBAB) as additive, and the palladacycle as catalyst are the most efficient conditions for the coupling with aryl bromides, good stereoselectivities being also obtained in the arylation of crotonates and itaconates, whereas cinnamic derivatives afford lower steroselectivity, with the exception of cinnamic acid and nitrile. β,β-Diarylation of unsubstituted α,β-unsaturated carbonyl compounds can be controlled by using higher loading of the palladacycle and can be performed in refluxing water for aryl iodides, whereas DMA must be used for aryl bromides. Microwave irradiation can be used in the monoarylation of tertbutyl acrylate with aryl iodides in water or the coupling between ethyl cinnamate and aryl bromides in aqueous DMA.