The coupling reaction between ethyl acetoacetate and a number of aryl halides in the presence of palladium acetate, a bulky and electron rich phosphine and K3PO4 is described. The arylated acetoacetate ester is de-acylated under the reaction conditions resulting in the generation of 2-arylacetic acid esters, constituting a mild alternative to direct arylation of carboxylate esters.
Reference:
Zeevaart, JG, Parkinson, CJ and De Koning, CB. 2004. Palladium-catalysed arylation of acetoacetate esters to yield 2-arylacetic acid esters. Tetrahedron Letters, vol. 45(22), pp 4261-4264
Zeevaart, J., Parkinson, C., & De Koning, C. (2004). Palladium-catalysed arylation of acetoacetate esters to yield 2-arylacetic acid esters. http://hdl.handle.net/10204/1502
Zeevaart, JG, CJ Parkinson, and CB De Koning "Palladium-catalysed arylation of acetoacetate esters to yield 2-arylacetic acid esters." (2004) http://hdl.handle.net/10204/1502
Zeevaart J, Parkinson C, De Koning C. Palladium-catalysed arylation of acetoacetate esters to yield 2-arylacetic acid esters. 2004; http://hdl.handle.net/10204/1502.
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