Chinese Journal of Organic Chemistry >
Base-Catalyzed Chemoselective Substitution of β-Ketonitrile with Azodicarboxylates
Received date: 2024-08-06
Revised date: 2024-10-27
Online published: 2024-11-28
Supported by
National Natural Science Foundation of China(21563025); National Natural Science Foundation of China(22162022)
Base-catalyzed nucleophilic substitution reactions of β-ketonitrile with azodicarboxylates have been developed. A series of disubstituted C—N coupling products were obtained in good to excellent yields under Et3N catalysis. Monosubstitution C—N bond formation reaction catalyzed by K2CO3 also gave novel enol-based target products. This method is simple and mild, with good chemoselectivity, excellent substrate compatibility and tolerance for various functional groups, and achieves gram-scale synthesis. The reaction is a nucleophilic substitution process without the involvement of free radicals.
Key words： base-catalysis; β-ketonitrile; selective substitution; azodicarboxylate
Yishi Guo , Tian Sang , Yan Liu , Ping Liu . Base-Catalyzed Chemoselective Substitution of β-Ketonitrile with Azodicarboxylates[J]. Chinese Journal of Organic Chemistry, 2025 , 45(4) : 1249 -1260 . DOI: 10.6023/cjoc202408005
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