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Oxidation reagent selection
Oxidation reagent selection
Oxidation of an alcohol reaction scheme.
The selective oxidation of alcohols is a valuable reaction in the pharmaceutical industry (Caron et al., 2006), with significant work dedicated to making oxidations greener (Sheldon et al., 2002). The ACS Venn diagram of oxidants for the transformation of alcohols to aldehydes or ketones provides a lot of potential options. Of these, Oxone and sodium hypochlorite (NaOCl) are considered to offer the best balance between greenness, utility, and scalability.
Abbreviated Venn Diagram for oxidation reagents, only including reagents common to ACS and GSK tools.
Ideally, air would be used as an oxidant, minimising waste and hazards. This is recognised in the GSK reagent guide for oxidations (Adams et al., 2013). However, as with biocatalysis and PIPO, the scalability of these reagents is questioned. Hydrogen peroxide (at less than 30% concentration) is another green oxidant given the waste product is water.
Oxidation of alcohols to aldehydes or ketones reagent guide.
References
References
Large-scale oxidations in the pharmaceutical industry: Caron, S., Dugger, R.W., Ruggeri, S.G., Ragan, J.A., Ripin, D.H.B., Chem. Rev. 2006, 106, 2943-2989.
Green, catalytic oxidations of alcohols: Sheldon, R.A., Arends, I.W.C.E., ten Brink, G.-J. and Dijksman, A., Acc. Chem. Res. 2002, 35, 774-781.
Development of GSK’s reagent guides – embedding sustainability into reagent selection: Adams, J.P., Alder, C.M., Andrews, I., Bullion, A.M., Campbell-Crawford, M., Darcy, M.G., Hayler, J.D., Henderson, R.K., A. Oare, C.A., Pendrak, I., Redman, A.M., Shuster, L.E., Sneddon, H.F., and Walker, M.D., Green Chem. 2013, 15, 1542-1549.
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