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© Institut Pasteur
Cristaux de cellulase, enzyme purifiée de Clostridium thermocellum permettant la digestion de la cellulose. Image colorisée.
Publication : Tetrahedron

Few unexpected results from a Suzuki-Miyaura reaction

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Tetrahedron - 01 Jan 2012

Salanouve, E.; Retailleau, P.; Janin, Y. L.

Tetrahedron 2012, 68, 2135-2140

In the course of the synthesis of original anti-infectious compounds we focused on the palladium- catalyzed Suzuki-Miyaura aryl-aryl coupling reaction between 2-(3-ethoxy-5-iodo-1H-pyrazol-1-yl) pyridine and phenylboronic acid. A study of the reaction products obtained under different conditions (various ligands and solvents), not only provided us with insights to optimize this reaction but also with few side compounds, resulting from CH activation, along with the unexpected bis(3-ethoxy-1-(pyridin-2- yl)-1H-pyrazol-5-yl)palladium. Stochiometric experiments with this remarkably stable biscyclopalla- dated reagent and phenylhalides pointed out the occurrence of arylearyl coupling, possibly via palladium IV intermediates