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Direct synthesis of cinnamaldehyde derivatives by reaction of aryl bromides with 3,3-diacetoxypropene catalyzed by a palladium–tetraphosphine complex

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Abstract

The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane in combination with [Pd(C3H5)Cl]2 affords an efficient catalyst for the synthesis of cinnamaldehyde derivatives by reaction of aryl bromides with 3,3-diacetoxypropene. The reaction gave directly the cinnamaldehyde derivatives very selectively. The coupling reaction of heteroaryl bromides or sterically congested aryl bromides such as 2,4,6-trimethylbromobenzene also proceeds.

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  37. As a typical experiment, the reaction of aryl halide (1 mmol), 3,3-diacetoxypropene (0.516 g, 3 mmol), K2CO3 (0.414 g, 3 mmol) at 130 °C during 20 h in dry DMF (3 mL) in the presence of cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/1/2 [PdCl(C3H5)]2 complex under argon affords the corresponding cinnamaldehyde derivative after addition of water, extraction with ether or dichloromethane, separation, drying (MgSO4), evaporation and purification by chromatography on silica gel.

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Authors and Affiliations

  1. Laboratoire de Synthèse Organique, Faculté des Sciences de Saint Jérôme, UMR 6180 CNRS and Université d’Aix-Marseille III: “Chirotechnologies: catalyse et biocatalyse”, Avenue Escadrille Normandie-Niemen, 13397, Marseille Cedex 20, France

    Florian Berthiol, Henri Doucet & Maurice Santelli

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  1. Florian Berthiol
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  2. Henri Doucet
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  3. Maurice Santelli
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Correspondence to Henri Doucet or Maurice Santelli.

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Berthiol, F., Doucet, H. & Santelli, M. Direct synthesis of cinnamaldehyde derivatives by reaction of aryl bromides with 3,3-diacetoxypropene catalyzed by a palladium–tetraphosphine complex. Catal Lett 102, 281–284 (2005). https://doi.org/10.1007/s10562-005-5869-z

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  • DOI: https://doi.org/10.1007/s10562-005-5869-z

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