Title Photoinduced CC Bond Cleavage and Oxidation of Cycloketoxime Esters
Authors Zhao, Binlin
Tan, Hui
Chen, Cheng
Jiao, Ning
Shi, Zhuangzhi
Affiliation Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China.
Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China.
Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China.
Jiao, N (reprint author), Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China.
Keywords C-C activation
radical
cycloketoxime
oxygenation
photocatalysis
DMSO
CARBON-CARBON BONDS
IMINYL RADICALS
MOLECULAR-OXYGEN
OXIME ESTERS
BECKMANN REARRANGEMENT
ALKOXYSULFONIUM IONS
UNACTIVATED ALKENES
AEROBIC OXYGENATION
DIMETHYL-SULFOXIDE
FACILE SYNTHESIS
Issue Date 2018
Publisher CHINESE JOURNAL OF CHEMISTRY
Citation CHINESE JOURNAL OF CHEMISTRY. 2018, 36(11), 995-999.
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 CC 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.
URI http://hdl.handle.net/20.500.11897/568191
ISSN 1001-604X
DOI 10.1002/cjoc.201800206
Indexed SCI(E)
中国科技核心期刊(ISTIC)
Appears in Collections: 药学院
天然药物与仿生药物国家重点实验室

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