1167-43-7Relevant articles and documents
Teaching Old Compounds New Tricks: DDQ-Photocatalyzed C?H Amination of Arenes with Carbamates, Urea, and N-Heterocycles
Das, Somnath,Natarajan, Palani,K?nig, Burkhard
supporting information, p. 18161 - 18165 (2017/12/28)
The C?H amination of benzene derivatives was achieved using DDQ as photocatalyst and BocNH2 as the amine source under aerobic conditions and visible light irradiation. Electron-deficient and electron-rich benzenes react as substrates with moderate to good product yields. The amine scope of the reaction comprises Boc-amine, carbamates, pyrazoles, sulfonimides and urea. Preliminary mechanistic investigations indicate arene oxidation by the triplet of DDQ to radical cations with different electrophilicity and a charge transfer complex between the amine and DDQ as intermediate of the reaction.
Catalytic C-H imidation of aromatic cores of functional molecules: Ligand-accelerated Cu catalysis and application to materials- and biology-oriented aromatics
Kawakami, Takahiro,Murakami, Kei,Itami, Kenichiro
supporting information, p. 2460 - 2463 (2015/03/04)
Versatile imidation of aromatic C-H bonds was accomplished. In the presence of copper bromide and 6,6′-dimethyl-2,2′-bipyridyl, a range of aromatics, such as polycyclic aromatic hydrocarbons, aromatic bowls, porphyrins, heteroaromatics, and natural produc
Pd-catalyzed aryl C-H imidation with arene as the limiting reagent
Boursalian, Gregory B.,Ngai, Ming-Yu,Hojczyk, Katarzyna N.,Ritter, Tobias
supporting information, p. 13278 - 13281 (2013/09/24)
An amine-N-oxide-ligated palladium complex, in conjunction with a silver cocatalyst, catalyzes imidation of arenes by the reagent N- fluorobenzenesulfonimide. The reaction enables imidation of a variety of arenes at or below room temperature, requires no coordinating directing group on the substrate, and gives synthetically useful yields with only 1 equiv of arene. Mechanistic data implicate an unusual mechanism devoid of commonly invoked organometallic intermediates: oxidation of the Pd catalyst occurs as the turnover-limiting step, while C-H bond functionalization occurs subsequently at a high oxidation state of the catalyst.