111726-46-6Relevant articles and documents
Regioselective iodination of phenol and analogues using N-iodosuccinimide and p-toluenesulfonic acid
Bovonsombat, Pakorn,Leykajarakul, Juthamard,Khan, Chiraphorn,Pla-on, Kawin,Krause, Michael M.,Khanthapura, Pratheep,Ali, Rameez,Doowa, Niran
, p. 2664 - 2667 (2009)
Mild and highly regioselective monoiodination of phenol and analogues is achieved in high to excellent yields at room temperature with a combination of stoichiometric p-toluenesulfonic acid and N-iodosuccinimide.
Synthesis of Stannylated Aryl Imines and Amines via Aryne Insertion Reactions into Sn?N Bonds
Kran, Eva,Mück-Lichtenfeld, Christian,Daniliuc, Constantin G.,Studer, Armido
supporting information, p. 9281 - 9285 (2021/05/31)
The reaction of in situ generated arynes with stannylated imines to provide ortho-stannyl-aniline derivatives is reported. The readily prepared trimethylstannyl benzophenone imine is introduced as an efficient reagent to realize the aryne σ-insertion reaction. The imine functionality is an established N-protecting group and insertions proceed with good yields and good to excellent regioselectivities. The product anilines are valuable starting materials for follow-up chemistry thanks to the rich chemistry offered by the trimethylstannyl moiety.
Application of the palladium-catalysed norbornene-assisted catellani reaction towards the total synthesis of (+)-linoxepin and isolinoxepin
Qureshi, Zafar,Weinstabl, Harald,Suhartono, Marcel,Liu, Hongqiang,Thesmar, Pierre,Lautens, Mark
, p. 4053 - 4069 (2014/07/08)
Our ongoing effort towards the development of highly selective transition-metal-catalysed C-H activation processes has led to the expansion of the Catellani reaction. In a Pd0/PdII/Pd IV-catalysed domino reaction, an aryl iodide, alkyl iodide and tert-butyl acrylate were combined to synthesize the carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in our group and provides an excellent procedure for the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The enantioselective total synthesis of the natural product (+)-linoxepin has been accomplished in eight steps starting from commercial materials. The key Pd-catalysed Catellani step served to combine aryl iodide, alkyl iodide and tert-butyl acrylate in a domino sequence. By tuning the final Heck reaction, both the natural product and its structural isomer were synthesized. Copyright
