Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis

被引:68
|
作者
Liu, Dong [1 ]
Liu, Zhao-Ran [1 ]
Ma, Cong [1 ]
Jiao, Ke-Jin [1 ]
Sun, Bing [1 ]
Wei, Lei [1 ]
Lefranc, Julien [2 ]
Herbert, Simon [3 ]
Mei, Tian-Sheng [1 ]
机构
[1] Univ Chinese Acad Sci, State Key Lab Organometall Chem, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,Chinese Acad Sci, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Nuvisan Innovat Campus Berlin GmbH, D-13353 Berlin, Germany
[3] Bayer AG, Pharmaceut Res & Dev, D-13353 Berlin, Germany
关键词
arylation; Ni catalysis; organic electrochemistry; paired electrolysis; sulfoximines; C-H FUNCTIONALIZATION; COUPLING REACTIONS; AMINATION; CHLORIDES; ELECTROSYNTHESIS; ELECTROCHEMISTRY; SULFONAMIDES; PRECATALYST; STRATEGIES; OXIDATION;
D O I
10.1002/anie.202016310
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel strategy for the N-arylation of NH-sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a Ni-II species is crucial to promote the reductive elimination of a C-N bond from the resulting Ni-III species at room temperature.
引用
收藏
页码:9444 / 9449
页数:6
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