ChemCatChem
ChemCatChem
4 years ago

Diruthenium Diacetate Catalysed Aerobic Oxidation of Hydroxylamines and Improved Chemoselectivity by Immobilisation to Lysozyme

Diruthenium Diacetate Catalysed Aerobic Oxidation of Hydroxylamines and Improved Chemoselectivity by Immobilisation to Lysozyme
Luigi Messori, Sara Cretella, Giampiero D'Adamio, Tiziano Marzo, Andrea Goti, Francesca Cardona, Flavia Lupi
A new green method for the preparation of nitrones through the aerobic oxidation of the corresponding N,N-disubstituted hydroxylamines has been developed upon exploring the catalytic activity of a diruthenium catalyst, that is, [Ru2(OAc)4Cl]), in aqueous or alcoholic solution under mild reaction conditions (0.1 to 1 mol % catalyst, air, 50 °C) and reasonable reaction times. Notably, the catalytic activity of the dimetallic centre is retained after its binding to the small protein lysozyme. Interestingly, this new artificial metalloenzyme conferred complete chemoselectivity to the oxidation of cyclic hydroxylamines, in contrast to the diruthenium catalyst. Lysozyme support: The novel aerobic oxidation of hydroxylamines to nitrones catalyzed by Ru2(OAc)4Cl or its adduct with lysozyme [HEWL/Ru2(OAc)2] is reported. The coordination of the diruthenium moiety to the protein imparts complete chemoselectivity to the reaction, in contrast to the metallic complex alone.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/cctc.201701083

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