Preparation of carbon-13 labeled aldehydes, alcohols, and carboxylic acids via the carbonylation of organoboranes

Isotopically labeled materials play an important role in chemical and biological research. The regiospecific incorporation of carbon-13 has become increasingly important in recent years with the advent of multinuclear NMR and whole body multinuclear NMR. Organoboranes have been used to synthesize a wide variety of functionally substituted compounds. In recent years, organo-boranes have become important intermediates in the preparation of isotopically enriched compounds. The carbonylation of organoboranes proved, in this study, to be an ideal method for the incorporation of carbon-13 in functionally substituted aldehydes. The enriched aldehyde can then be oxidized to the corresponding carboxylic acid or be reduced to the corresponding alcohol in good yield.