Chemistry : A European Journal

Copper-induced alkyne-azide cycloaddition (CuAAC), popularly known as the click-reaction, is one of the most widely used synthetic methods in the design of supramolecular scaffoldings. Whether its catalytic or stoichiometric version is concerned, the involvement of two metals in the cycloaddition has been debated in the literature in the case of copper and other metals such as zinc. Research groups of the Institut de Chimie de Strasbourg (UMR 7177) and Osaka University (Prof. Hayashi) have demonstrated the cooperation between two different metals, bound in a ditopic phenanthroline-strapped porphyrin, in mediating a click reaction to form a rotaxane. Neither metal alone is able to induce the alkyne-azide cycloaddition. This tandem metal effect works best when the activating template effect combines the alkyne-copper phenanthroline complex with the affinity of the zinc porphyrin core for the azide reagent. This work, which appeared in Chemistry: A European Journal as a VIP Communication, is expected to trigger investigation of the use of ditopic ligands in the field of active metal templated click reactions and to lead to the use of various metals that are complementary to copper for catalytic events in functional rotaxanes.

 

 

 

Référence :

Y. Miyazaki, C. Kahlfuss, A. Ogawa, T. Matsumoto, J. A. Wytko, K. Oohora, T. Hayashi, J. Weiss

 

CuAAC in a Distal Pocket: Metal Active-Template Synthesis of Strapped-Porphyrin [2]Rotaxanes

Chemistry: A European Journal 2017, July 12^th doi: 10.1002/chem.201702553

 

Contact chercheur :

Jean Weiss Institut de Chimie de Strasbourg

Courriel : jweiss@unistra.fr