Direct synthesis of 3-arylpropionic acids by tetraphosphine/palladium catalysed Heck reactions of aryl halides with acrolein ethylene acetal |
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Authors: | Mhamed Lemhadri Maurice Santelli |
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Affiliation: | UMR 6180 CNRS and Université d'Aix-Marseille III: ’Chirotechnologies:catalyse et biocatalyse’, Laboratoire de Synthèse Organique, Faculté des Sciences de Saint Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France |
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Abstract: | Through the use of [PdCl(C3H5)]2/Cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides undergoes Heck reaction with acrolein ethylene acetal. With this acetal, the selective formation of 3-arylpropionic acids/esters was observed. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides. |
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Keywords: | Palladium Catalysis Heck reaction 3-Arylpropionic acids Aryl bromides Acrolein ethylene acetal |
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