Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters

• Published in: Molecules (Basel, Switzerland) Vol. 28; no. 6; p. 2667
• Main Authors: Chen, Pu, Huang, Huawen, Tan, Qi, Ji, Xiaochen, Zhao, Feng
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 15.03.2023; MDPI
• Subjects: acylation; Bonds; C-C bond cleavage; Carbon; Cleavage; Covalent bonds; cyanoalkylation; Esters; Free radicals; Nitrogen; oxime ester; Photocatalysis; radical reactions; Reaction mechanisms; Review; Styrene; radical reactions; C-C bond cleavage; cyanoalkylation; acylation; oxime ester
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28062667

The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed in the last few decades. Among them, the N-O bond cleavage of oxime esters leading to formation of nitrogen-centered radicals triggers adjacent C-C bond cleavage to produce carbon-centered free radicals, which has been virtually used in organic synthesis in recent years. Herein, we summarized the radical reactions involving oxime N-O bond and C-C bond cleavage through this special reaction form, including those from acyl oxime ester derivatives and cyclic ketoxime ester derivatives. These contents were systematically classified according to different reaction types. In this review, the free radical reactions involving acyl oxime esters and cyclic ketoxime esters after 2021 were included, with emphasis on the substrate scope and reaction mechanism.