Selective oxoammonium salt oxidations of alcohols to aldehydes and aldehydes to carboxylic acids

…, PP Pradhan, NB Blanck, JM Bobbitt, WF Bailey

Index: Qiu, Joseph C.; Pradhan, Priya P.; Blanck, Nyle B.; Bobbitt, James M.; Bailey, William F. Organic Letters, 2012 , vol. 14, # 1 p. 350 - 353

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Citation Number: 34

Abstract

The oxidation of alcohols to aldehydes using stoichiometric 4-acetamido-2, 2, 6, 6- tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in CH2Cl2 at room temperature is a highly selective process favoring reaction at the carbinol center best able to accommodate a positive charge. The oxidation of aldehydes to carboxylic acids by 1 in wet acetonitrile is also selective; the rate of the process correlates with the concentration of ...