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Fast Propene Dimerization Using Upper Rim‐Diphosphinated Calix[4]arenes as Chelators
Author(s) -
Lejeune Manuel,
Sémeril David,
Jeunesse Catherine,
Matt Dominique,
Lutz Pierre,
Toupet Loïc
Publication year - 2006
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505410
Subject(s) - propene , calixarene , chemistry , methylaluminoxane , catalysis , ligand (biochemistry) , medicinal chemistry , stereochemistry , polymer chemistry , combinatorial chemistry , organic chemistry , metallocene , molecule , receptor , biochemistry , polymer , polymerization
The complexes [NiBr 2 ⋅ 1 ] and [NiBr 2 ⋅ 2 ], containing the upper rim‐diphosphinated calixarenes 5,17‐bis(diphenylphosphino)‐25,26,27,28‐tetrapropoxycalix[4]arene ( 1 ) and 5,17‐dibromo‐11,23‐bis(diphenylphosphino)‐25,26,27,28‐tetrapropoxycalix[4]arene ( 2 ) were assessed as propene dimerization catalysts. Combined with methylaluminoxane, both complexes result in highly efficient dimerization catalysts displaying C 6 selectivities in the range 80–97% and activities that compare with the best reported systems, the latter using PCy 3 as ligand. The origin of the remarkable activities of the calixarene derivatives may be the ability of the diphosphine to undergo a periodic bite angle increase that incidentally favors the insertion step. Calixarenes such as 1 or 2 , which each incorporate two “stable” Ph 2 PAr moieties, constitute interesting alternatives to the use PCy 3 in propene dimerization.