Synthesis 2006(11): 1873-1881  
DOI: 10.1055/s-2006-942370
PAPER
© Georg Thieme Verlag Stuttgart · New York

Polyvinylpyridine, a Versatile Solid Phase for Coordinative Immobilisation of Palladium Precatalysts - Applications in Suzuki-Miyaura Reactions

Wladimir Solodenkoa, Klaas Menneckea, Carla Vogtb, Susan Gruhlb, Andreas Kirschning*a
a Institut für Organische Chemie, Universität Hannover, Schneiderberg 1b, 30167 Hannover, Germany
e-Mail: andreas.kirschning@oci.uni-hannover.de;
b Institut für Anorganische Chemie, Universität Hannover, Callinstraße 9, 30167 Hannover, Germany
Further Information

Publication History

Received 12 December 2005
Publication Date:
05 May 2006 (online)

Abstract

The immobilisation of an oxime-based palladacycle on polyvinylpyridine (PVP) resin affords a reusable, air, moisture and thermally stable palladium precatalyst which exerts high activity in Suzuki-Miyaura reactions both in batch as well as continuous-flow processes. Evidence is presented which shows that, besides serving as an anchor for the precatalyst, PVP also acts as a scavenger for Pd particles present in solution.

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From in industrial point of view, it is commonly advantageous to promote continuous addition of reactants to an immobilised catalyst compared to repeatedly carrying out batch-wise procedures with the same catalyst. Indeed, each reisolation of the catalysts exerts stress on it which leads to reduced performance in the next run.

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Part of this work was presented at the 8th International Symposium on Solid-Phase Synthesis & Combinatorial Libraries, 2-6 September, 2003, at Imperial College London, UK.