19591-17-4Relevant articles and documents
A tandem highly stereoselective FeCl3-promoted synthesis of a bisindoline: Synthetic utility of radical cations in heterocyclic construction
Thomas, Noel F.,Velu, Saraswati S.,Weber, Jean-Frédéric F.,Lee,Hadi, A. Hamid A.,Richomme, Pascal,Rondeau, David,Noorbatcha, Ibrahim,Awang, Khalijah
, p. 11733 - 11742 (2004)
A conceptually distinctive stereoselective construction of the novel dimer, N-[N′-acetyl-7,7′-bis-(3,4-dimethoxy-phenyl)-7,8,7′,8′- tetrahydro-N′H-[8,8′]biindolyl-N-yl]-ethanone 25 (bisindoline) is described below. These structures, which include 7-(3,4-dimethoxyphenyl)- indoline 24 (veratryl indoline), were obtained by the tactical combination of palladium-catalysed coupling which produced 10-acetamido-3,4-dimethoxystilbene 9, followed by FeCl3 induced oxidative cyclization/dimerization. All new structures were fully characterized by 1- and 2D NMR spectroscopy, (proton, carbon-13, COSY, HMBC, HMQC) and mass spectrometry. Configurational assignments were further supported by semi-empirical AM1 calculations. Mechanistic interpretations, consistent with our results, are discussed. Graphical Abstract
Direct para-Selective C-H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines
Chen, Yujie,Huang, Zhibin,Jiang, Yaqiqi,Shu, Sai,Yang, Shan,Shi, Da-Qing,Zhao, Yingsheng
, p. 8226 - 8235 (2021/06/28)
Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C-H amination reaction.
Complementary Site-Selective Halogenation of Nitrogen-Containing (Hetero)Aromatics with Superacids
Mamontov, Alexander,Martin-Mingot, Agnès,Métayer, Benoit,Karam, Omar,Zunino, Fabien,Bouazza, Fodil,Thibaudeau, Sébastien
supporting information, p. 10411 - 10416 (2020/07/30)
Site-selective functionalization of arenes that is complementary to classical aromatic substitution reactions remains a long-standing quest in organic synthesis. Exploiting the generation of halenium ion through oxidative process and the protonation of the nitrogen containing function in HF/SbF5, the chlorination and iodination of classically inert Csp2?H bonds of aromatic amines occurs. Furthermore, the superacid-promoted (poly)protonation of the molecules acts as a protection, favoring the late-stage selective halogenation of natural alkaloids and active pharmaceutical ingredients.