1167-43-7Relevant academic research and scientific papers
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.
TRANSITION METAL-CATALYZED IMIDATION OF ARENES
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Paragraph 00198, (2015/03/13)
The present invention provides novel transition metal complexes (e.g., complexes of any one of Formulae (C1) to (C25)) that include an amine-N-oxide motif. The invention also provides methods of using these transition metal complexes in preparing N-aryl or N- heteroaryl sulfonimides (e.g., compounds of Formula (I)) and aryl or heteroaryl amines (e.g., compounds of Formula (II)). The inventive methods involve imidation of arenes and heteroarenes (e.g., compounds of Formula (A)) using an imidating agent (e.g., a compound of Formula (B), such as N-fluorobenzenesulfonimide (NFBS or NFSI)) in the presence of a single-electron reductant (e.g., an Ag(I) or Ru(II) salt).
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
Nickel-Catalyzed Desulfitative Suzuki-Miyaura Cross-Coupling of N,N-Disulfonylmethylamines and Arylboronic Acids
Chen, Liangshun,Lang, Hongyue,Fang, Lei,Yu, Jianjun,Wang, Limin
supporting information, p. 6385 - 6389 (2016/02/18)
A nickel-catalyzed approach for the synthesis of biaryl compounds from N,N-disulfonylmethylamines and arylboronic acids has been developed. Instead of arenesulfonyl chlorides, various N,N-disulfonylmethylamines were used as the aryl source through extrusion of SO2 to give cross-coupling products in moderate to good yields. A NiCl2(dppp)-catalyzed [dppp = 1,3-bis(diphenylphosphino)propane] desulfitative Suzuki-Miyaura cross-coupling reaction between N,N-disulfonylmethylamines and arylboronic acids is described for the first time. The biaryl compounds are obtained in moderate to good yields.
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.
