Catalytic Behaviour of Calixarenylphosphanes in Nickel-Catalysed Suzuki-Miyaura Cross-Coupling

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• 作者：Laure Monnereau ; David Sé ; meril ; Dominique Matt and Christophe Gourlaouen
• 刊名：European Journal of Inorganic Chemistry
• 出版年：2017
• 出版时间：January 18, 2017
• 年：2017
• 卷：2017
• 期：3
• 页码：581-586
• 全文大小：785K
• ISSN：1099-0682c

文摘

Two upper-rim-functionalised calix[4]arenes, 5-diphenylphosphino-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 catalytic activities are higher than those observed for other triarylphosphanes, 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.