Ruthenium-catalyzed oxidative cleavage of alkynes to carboxylic acids

…, F Chen, ZM Dong, DW Zhang

Index: Yang, Dan; Chen, Fei; Dong, Ze-Min; Zhang, Dan-Wei Journal of Organic Chemistry, 2004 , vol. 69, # 6 p. 2221 - 2223

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Citation Number: 50

Abstract

We describe an efficient method for the oxidative cleavage of alkynes to carboxylic acids using a combination of RuO2/Oxone/NaHCO3 in a CH3CN/H2O/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%). 1H NMR spectroscopy and ESI-MS experiments provided evidence for α-diketones and anhydrides as possible intermediates ...