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Catalytic Behaviour of Calixarenylphosphanes in Nickel‐Catalysed Suzuki–Miyaura Cross‐Coupling
Author(s) -
Monnereau Laure,
Sémeril David,
Matt Dominique,
Gourlaouen Christophe
Publication year - 2017
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201601351
Subject(s) - catalysis , phenylboronic acid , aryl , chemistry , nickel , ligand (biochemistry) , medicinal chemistry , halogenation , oxidative addition , tetra , coupling reaction , organic chemistry , polymer chemistry , alkyl , biochemistry , receptor
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 PPh 3 and P( o ‐tolyl) 3 as well as the Buchwald‐type ligand o ‐biph‐PPh 2 [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.