A Chemometric Approach to Map Reaction Media Chemoselectivity: Example of Selective Debenzylation
Fiche publication
Date publication
avril 2010
Auteurs
Membres identifiés du Cancéropôle Est :
Dr WAGNER Alain
Tous les auteurs :
Bensel N, Klar D, Catala C, Schneckenburger P, Hoonakker F, Goncalves S, Wagner A
Lien Pubmed
Résumé
A chemometric process consisting in measuring the reactivity of a set of substrates under standardized and complementary reaction conditions was run to evaluate the possibility of building a coherent database that would give a general overview of the selectivity of a variety of catalysts. This systematic experimental approach was applied to the hydrogenolysis of O-benzyl ether compounds. Analysis of collected data revealed reaction conditions with precise chemoselectivity. For instance, Pd/C in EtOH or PdOH in THF enabled the specific cleavage of the benzyl group in the presence of p-CF3Bn groups, and addition of triethylamine in EtOH suppressed the cleavage of the phenoxybenzyl bond. The latter selectivity was exemplified on several polyfunctional substrates.
Référence
Eur J Org Chem. 2010 Apr;12:2261-4