1232169-16-2Relevant articles and documents
Nitration of heteroaryltrimethyltins by tetranitromethane and dinitrogen tetroxide: Mechanistic aspects, scope and limitations
Fargeas, Valerie,Favresse, Fabien,Mathieu, Didier,Beaudet, Isabelle,Charrue, Pierre,Lebret, Bruno,Piteau, Marc,Quintard, Jean-Paul
, p. 1711 - 1721 (2003)
The nitration of 2-(trimethylstannyl)heteroarenes by tetranitromethane (TNM) or dinitrogen tetroxide has been shown to be possible when the HOMO energy of the heteroaryltin is high enough to allow the formation of the corresponding radical cation. The reaction proceeds through a charge-transfer complex between heteroaryltin and TNM, followed by a single-electron transfer, which is enhanced under sun-lamp irradiation. Accordingly, 2-nitrobenzo[b]furan, 2-nitrobenzo[b]thiophene, 2-nitropyridine and 2-nitroindoles were obtained by this method. However, the nitration of 2-stannylated pyrimidine or of stannylated 1,3,5-triazines has been shown to be impossible, due to the low energy of their HOMO orbitals. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Bismuth nitrate as a source of nitro radical in ipso-nitration of carboxylic acids
Agasti, Soumitra,Maiti, Siddhartha,Maity, Soham,Anniyappan,Talawar,Maiti, Debabrata
, p. 120 - 124 (2019)
Aromatic nitro compounds are extensively used in synthetic chemistry. We disclose a new approach to obtain nitroarenes regioselectively starting from carboxylic acids under acid-free reaction conditions.
Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer
Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua
, p. 9561 - 9568 (2021/08/06)
A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.
Substitution of the nitro group with Grignard reagents: Facile arylation and alkenylation of pyridine N-oxides
Zhang, Fang,Zhang, Song,Duan, Xin-Fang
supporting information, p. 5618 - 5620 (2013/01/15)
The unprecedented substitution of a nitro group with aryl or alkenyl groups of Grignard reagents affords 2-aryl or alkenylpyridine N-oxides in modest to high yields with high chemoselectivity. This protocol allows a simple and clean synthesis of various 2
