29810-10-4Relevant articles and documents
Ir-Catalyzed Ligand-Free Directed C-H Borylation of Arenes and Pharmaceuticals: Detailed Mechanistic Understanding
Mahamudul Hassan, Mirja Md,Mondal, Biplab,Singh, Sukriti,Haldar, Chabush,Chaturvedi, Jagriti,Bisht, Ranjana,Sunoj, Raghavan B.,Chattopadhyay, Buddhadeb
supporting information, p. 4360 - 4375 (2022/03/16)
An efficient method for Ir-catalyzed ligand free ortho borylation of arenes (such as, 2-phenoxypyridines, 2-anilinopyridines, benzylamines, benzylpiperazines, benzylmorpholines, benzylpyrrolidine, benzylpiperidines, benzylazepanes, α-amino acid derivatives, aminophenylethane derivatives, and other important scaffolds) and pharmaceuticals has been developed. The reaction underwent via an interesting mechanistic pathway, as revealed by the detailed mechanistic investigations by using kinetic isotope studies and DFT calculations. The catalytic cycle is found to involve the intermediacy of an Ir-boryl complex where the substrate C-H activation is the turnover determining step, intriguingly without any appreciable primary KIE. The method displays a broad range of substrate scope and functional group tolerance. Numerous late-stage borylation of various important molecules and drugs were achieved using this developed strategy. The borylated compounds were further converted into more valuable functionalities. Moreover, utilizing the benefit of the B-N intramolecular interaction of the mono borylated compounds, an operationally simple method has been developed for the selective diborylation of 2-phenoxypyridines and numerous functionalized arenes. Furthermore, the synthetic utility has been showcased with the removal of the pyridyl directing group from the borylated product to achieve ortho borylated phenol along with the ipso-borylation for the preparation of 1,2-diborylated benzene.
A formal method for the de-N,N-dialkylation of Sommelet-Hauser rearrangement products
Tayama, Eiji,Sato, Ryota,Takedachi, Keisuke,Iwamoto, Hajime,Hasegawa, Eietsu
, p. 4710 - 4718 (2012/07/28)
Selective amine de-alkylation enables the conversion of Sommelet-Hauser rearrangement products into 2-aryl-2-bromoacetic acid derivatives. These compounds are valuable synthetic intermediates in the synthesis of α-aryl-α-amino or α-aryl-β-amino acid deriv
Discovery of triarylethanolamine inhibitors of the Kv1.5 potassium channel
Beshore, Douglas C.,Liverton, Nigel J.,McIntyre, Charles J.,Claiborne, Christopher F.,Libby, Brian,Culberson, J. Christopher,Salata, Joseph J.,Regan, Christopher P.,Lynch, Joseph J.,Kiss, Laszlo,Spencer, Robert H.,Kane, Stephanie A.,White, Rebecca B.,Yeh, Suzie,Hartman, George D.,Dinsmore, Christopher J.
scheme or table, p. 2493 - 2496 (2010/08/06)
A series of triarylethanolamine inhibitors of the Kv1.5 potassium channel have been prepared and evaluated for their effects in vitro and in vivo. The structure-activity relationship (SAR) studies described herein led to the development of potent, selecti
