Alacid, Emilio; Najera, Carmen published an article in European Journal of Organic Chemistry. The title of the article was 《Acrolein diethyl acetal: a three-carbon homologating reagent for the synthesis of β-arylpropanoates and cinnamaldehydes by Heck reaction catalyzed by a Kaiser oxime resin derived palladacycle》.Electric Literature of C11H13ClO2 The author mentioned the following in the article:
A polymer palladacycle derived from Kaiser oxime resin was used as a source of palladium(0) in the chemoselective Heck reaction of acrolein di-Et acetal with aryl halides under ligand-free conditions. The use of typical Heck conditions afforded 3-arylpropionic esters, and the process can be directed to the synthesis of cinnamaldehydes under Cacchi conditions. These processes take place with rather low loading of the catalyst, which can be recovered by simple filtration and reused for at least five runs without competitive dehalogenation. This is the first time that a supported palladium complex has been reused under Cacchi conditions. ICP-OES analyses of the Pd content of the crude products in both transformations indicated lower leaching for the esters than for the aldehydes in the range up to 0.08 ppm for the esters and 0.8 ppm for the aldehydes. In the experiment, the researchers used Ethyl 3-(4-chlorophenyl)propanoate(cas: 7116-36-1Electric Literature of C11H13ClO2)
Ethyl 3-(4-chlorophenyl)propanoate(cas: 7116-36-1) belongs to organochlorine compounds. Alkanes and aryl alkanes may be chlorinated under free radical conditions, with UV light. Electric Literature of C11H13ClO2 The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics