The complex [PdCl2(P-N)] containing the basic and sterically demanding 8-(di-tert-butylphosphinooxy)quinoline ligand (P-N) is a highly efficient catalyst for the coupling of phenylboronic acid with aryl bromides or aryl chlorides. The influence of solvent and base has been investigated, the highest rates being observed at 110 C in toluene with K2CO3 as the base. With aryl bromides the reaction rates are almost independent on the electronic properties of the para aryl substituents, on the contrary, reduced reaction rates are observed when bulky substituents are present on the substrate. Nevertheless the coupling of 2-bromo-1,3,5-trimethylbenzene with phenylboronic acid can be carried out to completion in 2 h using a catalyst loading of 0.02 mol %. Under optimized reaction conditions, turnover frequencies as high as 1900 h(-1) can be obtained in the coupling of 4-chloroacetophenone with phenylboronic acid: lower reaction rates are obtained with Substrates bearing EDG substituents on the aryl group. (C) 2009 Elsevier Ltd. All rights reserved.

Scrivanti, A., Bertoldini, M., Matteoli, U., Antonaroli, S., Crociani, B. (2009). [PdCl2{8-(di-tert-butylphosphinooxy)quinoline)}]: a highly efficient catalyst for Suzuki-Miyaura reaction. TETRAHEDRON, 65(36), 7611-7615 [10.1016/j.tet.2009.06.099].

[PdCl2{8-(di-tert-butylphosphinooxy)quinoline)}]: a highly efficient catalyst for Suzuki-Miyaura reaction

ANTONAROLI, SIMONETTA;CROCIANI, BRUNO
2009-07-02

Abstract

The complex [PdCl2(P-N)] containing the basic and sterically demanding 8-(di-tert-butylphosphinooxy)quinoline ligand (P-N) is a highly efficient catalyst for the coupling of phenylboronic acid with aryl bromides or aryl chlorides. The influence of solvent and base has been investigated, the highest rates being observed at 110 C in toluene with K2CO3 as the base. With aryl bromides the reaction rates are almost independent on the electronic properties of the para aryl substituents, on the contrary, reduced reaction rates are observed when bulky substituents are present on the substrate. Nevertheless the coupling of 2-bromo-1,3,5-trimethylbenzene with phenylboronic acid can be carried out to completion in 2 h using a catalyst loading of 0.02 mol %. Under optimized reaction conditions, turnover frequencies as high as 1900 h(-1) can be obtained in the coupling of 4-chloroacetophenone with phenylboronic acid: lower reaction rates are obtained with Substrates bearing EDG substituents on the aryl group. (C) 2009 Elsevier Ltd. All rights reserved.
2-lug-2009
Pubblicato
Rilevanza internazionale
Articolo
Sì, ma tipo non specificato
Settore CHIM/07 - FONDAMENTI CHIMICI DELLE TECNOLOGIE
English
Con Impact Factor ISI
Aryl halides; C-C coupling; P,N ligands; Palladium; Suzuki-Miyaura reaction
Scrivanti, A., Bertoldini, M., Matteoli, U., Antonaroli, S., Crociani, B. (2009). [PdCl2{8-(di-tert-butylphosphinooxy)quinoline)}]: a highly efficient catalyst for Suzuki-Miyaura reaction. TETRAHEDRON, 65(36), 7611-7615 [10.1016/j.tet.2009.06.099].
Scrivanti, A; Bertoldini, M; Matteoli, U; Antonaroli, S; Crociani, B
Articolo su rivista
File in questo prodotto:
File Dimensione Formato  
Tetrahedron2009.pdf

accesso aperto

Descrizione: Articolo principale
Dimensione 451.13 kB
Formato Adobe PDF
451.13 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2108/23672
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 19
  • ???jsp.display-item.citation.isi??? 19
social impact