The preparation of the new ligand 8-(di-tert-butylphosphinooxy) quinoline (1) and the palladium derivatives [PdCl2(1)] (2), [Pd(eta(3)-all)(1)](+) [all = C3H5 (3a), 1-PhC3H4 (3b) and 1,3-Ph2C3H3 (3c)] and [Pd(eta(2)ol)(1)] [ol = dimethyl fumarate (4a) and fumaronitrile (4b)] is reported. The cationic species 3a-3c have been isolated as BF4- salts. The complex 3a(BF4) is obtained either from the reaction of 1 with [Pd(mu-Cl)(eta(3)-C3H5)](2) or from the reaction of ClP(CMe3)(2) with [Pd(eta(3)-C3H5)(8-oxyquinoline)], followed in both cases by chloride abstraction with NaBF4. In the complexes, the ligand 1 is P,N chelated to the central metal, as shown by the X-ray structural analysis of 3a( BF4). At 25 degrees C in solution, 3a(BF4) and 3b(BF4) undergo a fast eta(3) - eta(1) - eta(3) dynamic process which brings about a syn-anti exchange only for the allylic protons cis to phosphorus, while for 4a and 4b a slow rotation of the olefin around its bond axis to palladium takes place. The complexes 2 and 3a(BF4) are efficient catalyst precursors in the coupling of the phenylboronic acid with aryl bromides and chlorides. (C) 2008 Elsevier B. V. All rights reserved.

Crociani, B., Antonaroli, S., Burattini, M., Benetollo, F., Scrivanti, A., Bertoldini, M. (2008). Palladium complexes of 8-(di-tert-butylphosphinooxy) quinoline. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 693(26), 3932-3938 [10.1016/j.jorganchem.2008.10.001].

Palladium complexes of 8-(di-tert-butylphosphinooxy) quinoline

CROCIANI, BRUNO;ANTONAROLI, SIMONETTA;
2008-10-08

Abstract

The preparation of the new ligand 8-(di-tert-butylphosphinooxy) quinoline (1) and the palladium derivatives [PdCl2(1)] (2), [Pd(eta(3)-all)(1)](+) [all = C3H5 (3a), 1-PhC3H4 (3b) and 1,3-Ph2C3H3 (3c)] and [Pd(eta(2)ol)(1)] [ol = dimethyl fumarate (4a) and fumaronitrile (4b)] is reported. The cationic species 3a-3c have been isolated as BF4- salts. The complex 3a(BF4) is obtained either from the reaction of 1 with [Pd(mu-Cl)(eta(3)-C3H5)](2) or from the reaction of ClP(CMe3)(2) with [Pd(eta(3)-C3H5)(8-oxyquinoline)], followed in both cases by chloride abstraction with NaBF4. In the complexes, the ligand 1 is P,N chelated to the central metal, as shown by the X-ray structural analysis of 3a( BF4). At 25 degrees C in solution, 3a(BF4) and 3b(BF4) undergo a fast eta(3) - eta(1) - eta(3) dynamic process which brings about a syn-anti exchange only for the allylic protons cis to phosphorus, while for 4a and 4b a slow rotation of the olefin around its bond axis to palladium takes place. The complexes 2 and 3a(BF4) are efficient catalyst precursors in the coupling of the phenylboronic acid with aryl bromides and chlorides. (C) 2008 Elsevier B. V. All rights reserved.
8-ott-2008
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore CHIM/07 - FONDAMENTI CHIMICI DELLE TECNOLOGIE
English
Con Impact Factor ISI
Palladium organometallic complexes; Phosphinito-quinoline ligands; Solution and solid state structure; Suzuki-Miyaura reaction
Crociani, B., Antonaroli, S., Burattini, M., Benetollo, F., Scrivanti, A., Bertoldini, M. (2008). Palladium complexes of 8-(di-tert-butylphosphinooxy) quinoline. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 693(26), 3932-3938 [10.1016/j.jorganchem.2008.10.001].
Crociani, B; Antonaroli, S; Burattini, M; Benetollo, F; Scrivanti, A; Bertoldini, M
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/26945
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