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Resorcin[4]arene‐Derived Mono‐ and Diphosphines in Suzuki Cross‐Coupling
Author(s) -
El Moll Hani,
Sémeril David,
Matt Dominique,
Toupet Loïc
Publication year - 2010
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.200900767
Subject(s) - cavitand , chemistry , phosphine , phenylboronic acid , aryl , diphosphines , catalysis , ligand (biochemistry) , medicinal chemistry , suzuki reaction , photochemistry , polymer chemistry , organic chemistry , palladium , molecule , supramolecular chemistry , biochemistry , alkyl , receptor
Three resorcin[4]arene cavitands ( 1 – 3 ) having either one or two resorcinolic C‐2 atoms substituted by a CH 2 PPh 2 podand arm were assessed in the Suzuki arylation of aryl bromides with phenylboronic acid. Using P:Pd ratios of 2:1 and operating in dioxane at 100 °C with a catalyst loading of 0.001 mol% resulted in highly efficient catalytic systems. For example, TOFs up to 34570 mol(converted ArBr)⋅mol(Pd) −1 ⋅h −1 were obtained with the proximally‐disubstituted cavitand 3 when using 4‐bromotoluene as substrate. The performance was shown to vary in the following order: monophosphine 1