Photoinduced C—C Bond Cleavage and Oxidation of Cycloketoxime Esters1. Issue 11 (14th September 2018)

• Record Type: Journal Article
• Authors: Zhao, Binlin; Tan, Hui; Chen, Cheng; Jiao, Ning; Shi, Zhuangzhi
• Is Part Of: Chinese journal of chemistry. Volume 36:Issue 11(2018)
• Page Start: 995
• Page End: 999
• Publication Date: 2018-09-14
• Subjects: C—C activation -- radical -- cycloketoxime -- oxygenation -- photocatalysis -- DMSO; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201800206
• Languages: English
• ISSNs: 1001-604X

Abstract

Abstract: A novel structural reorganization of cycloketoxime esters beyond the traditional Beckmann rearrangement process has been established to build cyano‐containing ketones in the presence of photocatalyst. This novel transformation is remarkable with selective C—C bond cleavage and an oxidation process enabled by DMSO used as the solvent, oxidant, and oxygen source avoiding acid, base and toxic cyanide salts as the cyano source. Further applications in late‐stage modification of complex and chiral molecules have also been reported. Abstract : A SET‐induced strategy has been established for C—C bond cleavage and oxidation sequence of cycloketoxime esters in the presence of photocatalyst. The protocol is distinguished by mild and safe reaction conditions that avoid peroxide, acid, base and toxic cyanide salts.