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Article Dans Une Revue European Journal of Inorganic Chemistry Année : 2017

Catalytic Behaviour of Calixarenylphosphanes in Nickel‐Catalysed Suzuki–Miyaura Cross‐Coupling

Résumé

Two upper-rim-functionalised calix[4]arenes, 5-di- phenylphosphino-25,26,27,28-tetra-benzyloxycalix[4]arene and 5-diphenylphosphino-25,26,27,28-tetra-(p-anisyl)methyloxy calix- [4]arene, were investigated in the nickel-catalysed cross- coupling of phenylboronic acid with aryl bromides. The cata- lytic activities are higher than those observed for other tri- arylphosphanes, notably PPh3 and P(o-tolyl)3 as well as the Buchwald-type ligand o-biph-PPh2 [TOFs up to 2600 mol(ArPh) mol(Ni)–1 h–1], but the production of large amounts of dehalogenation product could not be avoided, thus strongly contrasting with the classical Pd-catalysed reaction. Good activities were also obtained with aryl chlorides, even at room temperature. The higher efficiency of 1 and 2 relative to that of the Buchwald ligand 3 probably arises from the ease with which these two calix–phosphanes may form appropriate monophosphine complexes before the oxidative addition step.

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Catalyse
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Dates et versions

hal-03515914 , version 1 (06-01-2022)

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Citer

Laure Monnereau, David Sémeril, Dominique Matt, Christophe Gourlaouen. Catalytic Behaviour of Calixarenylphosphanes in Nickel‐Catalysed Suzuki–Miyaura Cross‐Coupling. European Journal of Inorganic Chemistry, 2017, 2017 (3), pp.581-586. ⟨10.1002/ejic.201601351⟩. ⟨hal-03515914⟩
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