31054-06-5Relevant academic research and scientific papers
Electro-oxidative C-H amination of heteroarenes with aniline derivativesviaradical-radical cross coupling
Feng, Pengju,Hu, Shiyu,Ma, Guojian,Peng, Xichao,Ruan, Zhixiong,Wu, Yan,Zhao, Junhao
, p. 8853 - 8858 (2021/11/23)
The selective synthesis of C-2/C-3 aminated five-membered heteroarenes incorporated various functionalities with aniline derivatives in a sustainable way remains an unmet challenge. This protocol presents a practical protocol for the C-H amination of heteroarenesviaan electro-oxidative cross coupling process. This electrosynthetic approach enables a facile access to a wide variety of synthetically useful hetero-arene derivatives, tolerates a wide range of functional groups, and is amenable to gram scale synthesis. In addition, a preliminary mechanistic study reveals that a radical cross coupling process between the N-centered radical and indole radical cation may be involved for this amination reaction.
DIRECT AMINATION. Part 4. REACTIONS OF INDOLES WITH PRIMARY AROMATIC AMINES AND IODOSOBENZENE DIACETATE
Cardellini, Liberato,Greci, Lucedio,Maurelli, Eziana,Orena, Mario,Stipa, Pierluigi,Tosi, Giorgio
, p. 1917 - 1926 (2007/10/02)
Indole, 2-methylidole, 2-phenylindole, and primary aromatic amines react with iodosobenzene diacetate leading both to 2-arylamino-3-arylimino-3H-indole in the case of indole and 2-methylindole, and to 2-phenyl-3-arylimino-3H-indole in the case of 2-phenylindole.The reaction is believed to proceed through the formation of a nitrenium ion formed by the interaction of iodosobenzene diacetate and primary aromatic amines and the mechanism is supported by experimental evidences.The methyl elimination from 2-methylindole is explained on the basis of the isolation of the possible intermediate and the formation of an animal, whose decomposition leads to the reaction products.The intermediate animal is proposed on the basis of the bis-(2-methylindol-3-yl)methane formation.
Direct Amination. Part 2. Reaction of 2-Phenylindole with Primary Aromatic Amines. A Chemical and Electrochemical Investigation
Berti, Corrado,Greci, Lucedio,Andruzzi, Romano,Trazza, Antonio
, p. 607 - 610 (2007/10/02)
The reaction of 2-phenylindole with primary aromatic amines to form 2-phenyl-3-arylimino-3H-indoles, in the presence of N-chlorobenzotriazole, N-chloroisatin or lead tetraacetate, were also investigated by anodic oxidation.The chemical and electrochemical results suggest a mechanism involving an intermediate nitrenium ion, whose formation was demonstrated by an independent route.The reaction of 1-hydroxy-2-phenylindole with p-anisidine to form 2-phenyl-3-p-methoxyphenylimino-3H-indole 1-oxide, previously studied under anodic oxidation is here described in the presence of N-chlorobenzotriazole.
