The cleavage of a fatty 1,2-diketone derived from methyl oleate into the corresponding esters, i.e., methyl nonanoate and dimethyl azelate was studied by organocatalysis using oxygen as a clean oxidant. Only carbene generated from thiazolium salts and K 2 CO 3 could efficiently catalyze this transformation. It was found that, under the optimized conditions, the oxidative cleavage leads to the formation of a 1:1 mixture of esters and potassium carboxylates.An acidic treatment of the mixture, followed by esterification with methanol, led to the desired 2 esters with 75 and 77% yield. This protocol was extended to a range of symmetrical and unsymmetrical fatty 1,2-diketones and the corresponding esters were isolated with 61-84% yield.
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