K2CO3-accelerated amidation of carboxylic acids using α-oxo ketene-N,S-acetals as amine surrogates?
Organic Chemistry Frontiers Pub Date: 2022-12-07 DOI: 10.1039/D2QO01716D
Abstract
A novel and efficient K2CO3-accelerated amidation of carboxylic acids with α-oxo ketene-N,S-acetals as amine surrogates is developed. The amidation of carboxylic acids is achieved in the presence of 10 mol% of K2CO3 using readily available (E)-4-(alkylamino)-4-(ethylthio)but-3-en-2-ones as amine surrogates. The method represents the first example of the synthetic utility of C–N bond cleavage of α-oxo ketene-N,S-acetals. A plausible mechanism is proposed on the basis of the detailed studies, in which the base plays the key role during the transformation.
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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