Copper-Catalyzed para-Selective C-H Amination of Electron-Rich Arenes

ACS Catalysis 2015
Beatrise Bērziņa, Igors Sokolovs, Edgars Sūna

Electron-rich arenes such as anisole, dialkylbenzenes, and aniline and aryl ether derivs. underwent regioselective amination reactions with amines, amides, sulfonamides, and nitrogen heterocycles such as morpholine mediated by (hydroxy)(tosyloxy)aryliodanes and sulfonic acids in the presence of Cu(MeCN)4BF4 to yield para-substituted arylamines and arylated nitrogen heterocycles such as 4-(4-methoxyphenyl)morpholine in 20-82% yields. The reaction proceeded by generation of unsym. diaryl-λ3-iodanes in situ followed by copper-catalyzed amination. The structure of the unsym. diaryliodonium triflate 2,4,6-i-Pr3C6H2I+-3,4-Me2C6H3•OTf- was detd. by X-ray crystallog.

Keywords
Copper-Catalyzed para-Selective C-H Amination of Electron-Rich Arenes
DOI
10.1021/acscatal.5b01992
Hyperlink
http://pubs.acs.org/doi/10.1021/acscatal.5b01992

Bērziņa, B., Sokolovs, I., Sūna, E. Copper-Catalyzed para-Selective C-H Amination of Electron-Rich Arenes. ACS Catalysis, 2015, Vol.5, Iss.11, pp.7008-7014. ISSN 2155-5435. Available from: doi:10.1021/acscatal.5b01992

Publication language
English (en)