The Arylation of Activated Methylene Compounds

The arylation of activated methylene compounds mediated by copper salts is a well-established process, dating back to the Hurtly reaction in 1929. In the following reports of this process, high yields were only obtained with aryl hahdes bearing electron-withdrawing groups or ortho-substituents that could be 

Entry X Ligand Activated methylene compounds Reaction conditions Ref. 

Br 11 diethyl malonate, ethyl acetoacetate, ethyl benzoyl acetate Cul, CS2CO3 DMSO, 40-50°C [67] 

2 I U acetylacetone, ethyl cyanoacetate, malononitrile Cul, KjCOj DMSO, 90 C [68] 

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Sonochemistry has been applied to acceleration of the Reformatsky reaction, Diels-Alder reactions, the arylation of active methylene compounds nucleophilic aromatic substitution of haloarenes, and to hydrostannation and tin hydride reduction. " Other sonochemical applications involve the reaction of benzyl chloride and nitrobenzene, a Sr I reaction in liquid ammonia at room temperature, and Knoevenagel condensation of aromatic aldehydes. lodination of aliphatic hydrocarbons can be accelerated, and oxyallyl cations have been prepared from ot,ot -diiodoketones using sonochemistry. Sonochemistry has been applied to the preparation of carbohydrate compounds.When sonochemistry is an important feature of a chemical reaction, this fact will be noted in the reactions presented in Chapters 10-19. 

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