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A Chemometric Approach to Map Reaction Media Chemoselectivity: Example of Selective Debenzylation
Author(s) -
Bensel Nicolas,
Klär Daniel,
Catala Cédric,
Schneckenburger Patrick,
Hoonakker Frank,
Goncalves Sylvie,
Wagner Alain
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901497
Subject(s) - chemoselectivity , hydrogenolysis , chemistry , triethylamine , selectivity , cleavage (geology) , catalysis , reactivity (psychology) , ether , combinatorial chemistry , organic chemistry , medicine , alternative medicine , geotechnical engineering , pathology , fracture (geology) , engineering
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.