We describe an efficient method for the oxidative cleavage of alkynes to carboxylic acids using a combination of RuO(2)/Oxone/NaHCO(3) in a CH(3)CN/H(2)O/EtOAc solvent system. Both internal and terminal alkynes, regardless of their electron density, can be oxidized to carboxylic acids in excellent yield (up to 99%). (1)H NMR spectroscopy and ESI-MS experiments provided evidence for alpha-diketones and anhydrides as possible intermediates in these oxidation reactions.
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Yang et al. (2004) studied this question.
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