Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters

Peng-Jun Zhou; Cheng-Kun Li; Shao-Fang Zhou; Adedamola Shoberu; Jian-Ping Zou

doi:10.1039/c7ob00241f

Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters

Org Biomol Chem. 2017 Mar 22;15(12):2629-2637. doi: 10.1039/c7ob00241f.

Authors

Peng-Jun Zhou¹, Cheng-Kun Li¹, Shao-Fang Zhou¹, Adedamola Shoberu¹, Jian-Ping Zou¹

Affiliation

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, 199 Renai, Street, Suzhou, Jiangsu 215123, China. jpzou@suda.edu.cn.

PMID: 28267182
DOI: 10.1039/c7ob00241f

Abstract

A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.