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Synthesis 2012(1): 151-157  
DOI: 10.1055/s-0031-1289618
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

5-(p-Tolyl)isoxazol-3-amine-Palladium(II) Complex: Preparation, Structure, and Catalytic Application in the Suzuki-Miyaura Reaction in Water

Vladimir I. Potkin*a, Nikolay A. Bumagin*b, Sergey K. Petkevicha, Alexander S. Lyakhovc, Dmitrii A. Rudakova, Michail V. Livantsovb, Nikita E. Golantsovb
a Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Surganova Str., 13, Minsk 220072, Belarus
Fax: +375(17)2841679; e-Mail: potkin@ifoch.bas-net.by;
b M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1/3, Moscow 119991, Russian Federation
Fax: +7(495)9328846; e-Mail: bumagin@org.chem.msu.ru;
c Physico-Chemical Research Institute of Belarusian State University, Leningradskaya Str., 14, Minsk 220030, Belarus
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Publication History

Received 23 September 2011
Publication Date:
23 November 2011 (online)

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Abstract

A air and moisture stable square-planar trans-dichloropalladium(II) complex containing two 5-(p-tolyl)isoxazol-3-amine ligands was synthesized and structurally characterized by single-crystal X-ray diffraction. The isoxazol-3-amine ligand was prepared from 5-(p-tolyl)isoxazole-3-carbaldehyde oxime by successive transformations. The new complex is a high-turnover-number catalyst for the Suzuki-Miyaura reaction with low palladium loading (0.0001-0.1%) in neat water under an air atmosphere.

Key words

5-(p-tolyl)isoxazol-3-amine ligand - palladium complex - crystal structure - catalysis - Suzuki-Miyaura reaction - biaryls - water