Download PDF
Synfacts 2013; 9(6): 0675
DOI: 10.1055/s-0033-1338761
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Suzuki Coupling Using Co/C MNPs-Immobilized Dendritic Phosphine–Pd

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Aya Ohno
Keller M, Collière V, Reiser O, Caminade A.-M, * Majoral J.-P, * Ouali A. * LCC-CNRS, Toulouse and Université de Toulouse, France; Universität Regensburg, Germany
Pyrene-Tagged Dendritic Catalysts Noncovalently Grafted onto Magnetic Co/C Nanoparticles: An Efficient and Recyclable System for Drug Synthesis.

Angew. Chem. Int. Ed. 2013;
52: 3626-3629
CrossrefGoogle Scholar
Further Information

Publication History

Publication Date:
16 May 2013 (online)

 
 PDF Download Permissions and Reprints

Key words

magnetic Co/C nanoparticles - palladium - pyrene-tagged phosphine - Suzuki coupling

Significance

Pyrene-tagged mono- and penta-phosphine–palladium complexes were immobilized on graphene layers of magnetic Co/C nanoparticles through π–π interactions. The resulting catalysts 1 and 2 were applied to the Suzuki–Miyaura coupling of aryl bromides 1 and boronic acids 2 to afford the corresponding biaryls 3 in 70–98% yield (seven examples). These catalysts were separated from the reaction mixture by magnetic decantation.


#

Comment

Catalyst 2 was reused ten times without significant loss of catalytic activity (felbinac 3f, 1st use: 100% GC yield; 11th use: 100% GC yield). ICP-MS analysis for the first cycle showed that about 6% of the introduced palladium leached out into the crude mixture (111 ppm palladium). After the extraction with CH2Cl2, the contamination of palladium became less than 5 ppm, and no traces of cobalt were detected.


#
#


   Permissions and Reprints