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

• Published in: European Journal of Organic Chemistry Vol. 2010; no. 12; pp. 2261 - 2264
• Main Authors: Bensel, Nicolas, Klär, Daniel, Catala, Cédric, Schneckenburger, Patrick, Hoonakker, Frank, Goncalves, Sylvie, Wagner, Alain
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01-04-2010; WILEY‐VCH Verlag; Wiley-VCH
• Subjects: Catalysis; Catalysts: preparations and properties; Chemical reactivity; Chemistry; Chemoinformatics; Chemoselectivity; Exact sciences and technology; General and physical chemistry; Hydrogenation; Kinetics and mechanisms; Organic chemistry; Reactivity; Reactivity and mechanisms; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Polyfunctional compound; Ethanol; Ether; Chemoselectivity; Hydrogenolysis; Palladium; Selectivity; Experimental study; Chemoinformatics; Carbon; Hydrogenation; Tetrahydrofurane; Reactivity; Benzylic compound; Database; Cleavage; Debenzylation; Chemical reactivity; Platinoid; Catalyst; Chemometrics
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200901497

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.
A chemometric process consisting in measuring the reactivity of a tailored 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 data collection was applied to the hydrogenolysis of O‐benzyl ether compounds.