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Oxidations of Alcohols, Aldehydes, and Diols Using NaBr and Selectfluor
Harshit Joshi1, Debobrata Paul1, Shyam Sathyamoorthi1
1Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
Abstract:
We present protocols for the oxidation of alcohols and aldehydes and for the oxidative cyclization of diols which use a combination of Selectfluor and NaBr. For most substrates, the optimal solvent system is a 1:1 mixture of CH3CN/H2O, but, in select cases, biphasic 1:1 mixtures of EtOAc/H2O or CH2Cl2/H2O are superior. This procedure is operationally simple, uses inexpensive and readily available reagents, and tolerates a variety of functional groups. Mechanistic studies suggest that the active oxidant is hypobromous acid, generated by the almost instantaneous oxidation of Br- by Selectfluor in an aqueous milieu.
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