898786-66-8Relevant academic research and scientific papers
Radical C-C Bond Cleavage/Addition Cascade of Benzyl Cycloketone Oxime Ethers Enabled by Photogenerated Cyclic Iminyl Radicals
Wang, Peng-Zi,He, Bin-Qing,Cheng, Ying,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information, p. 6924 - 6929 (2019/09/30)
A light-driven, metal-free, and iminyl radical-mediated ring-opening C-C bond cleavage/addition cascade of O-4-methoxybenzyl oxime ethers and alkenes is described for the first time. The reaction shows a broad substrate scope and high functional group compatibility with both components, giving the corresponding valuable oxo nitriles in generally good yields. Key to the success of this protocol is the generation of cyclic iminyl radicals from the O-4-methoxybenzyl oxime ethers via a photocatalytic hydrogen atom transfer (HAT) process. The proposed main pathway is also supported by the preliminary mechanistic studies.
Photoinduced C—C Bond Cleavage and Oxidation of Cycloketoxime Esters
Zhao, Binlin,Tan, Hui,Chen, Cheng,Jiao, Ning,Shi, Zhuangzhi
, p. 995 - 999 (2018/09/25)
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.
