A Chemometric Approach to Map Reaction Media Chemoselectivity: Example of Selective Debenzylation

作者:Bensel Nicolas; Klaer Daniel; Catala Cedric; Schneckenburger Patrick; Hoonakker Frank; Goncalves Sylvie; Wagner Alain*
来源:European Journal of Organic Chemistry, 2010, (12): 2261-2264.
DOI:10.1002/ejoc.200901497

摘要

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-CF(3)Bn groups, and addition of triethylamine in EtOH suppressed the cleavage of the phenoxybenzyl bond. The latter selectivity was exemplified on several polyfunctional substrates.

  • 出版日期2010-4