Premium
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
Author(s) -
Alacid Emilio,
Nájera Carmen
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800047
Subject(s) - chemistry , heck reaction , acetal , palladium , reagent , catalysis , organic chemistry , oxime , aryl , acrolein , halogenation , leaching (pedology) , alkyl , environmental science , soil science , soil water
A polymer palladacycle derived from Kaiser oxime resin was used as a source of palladium(0) in the chemoselective Heck reaction of acrolein diethyl 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.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)