621-07-8Relevant articles and documents
Late Stage Functionalization of Secondary Amines via a Cobalt-Catalyzed Electrophilic Amination of Organozinc Reagents
Gra?l, Simon,Chen, Yi-Hung,Hamze, Clémence,Tüllmann, Carl Phillip,Knochel, Paul
supporting information, p. 494 - 497 (2019/01/14)
A general preparation of polyfunctional hydroxylamine benzoates from the corresponding secondary amines is reported. This convenient synthesis allows the setup of a late-stage functionalization of various secondary amines, including pharmaceuticals and peptidic derivatives. Thus, a cross-coupling of hydroxylamine benzoates with various alkyl-, aryl-, and heteroaryl-zinc chlorides in the presence of 5 mol % CoCl2 (25 °C, 2 h) provides a range of polyfunctional tertiary amines. This method was used to prepare penfluridol and gepirone.
Copper-Catalyzed Ring Opening of Benzofurans and an Enantioselective Hydroamination Cascade
Xu-Xu, Qing-Feng,Liu, Qiang-Qiang,Zhang, Xiao,You, Shu-Li
supporting information, p. 15204 - 15208 (2018/10/24)
A copper(II) acetate/(R)-DTBM-SEGPHOS-catalyzed ring opening of benzofurans and enantioselective hydroamination cascade with dimethoxymethylsilane (DMMS) and hydroxylamine esters is described. Starting from readily available substituted benzofurans, a series of chiral N,N-dibenzylaminophenols, which are of high interest in pharmaceutical chemistry, were obtained with excellent enantioselectivities (up to 66 % yield, 94 % ee).
Selective Oxidation of Secondary Amines to N,N-Disubstituted Hydroxylamines by Choline Peroxydisulfate
Banan, Alireza,Valizadeh, Hassan,Heydari, Akbar,Moghimi, Abolghasem
, p. 2315 - 2319 (2017/10/06)
N,N-Disubstituted hydroxylamines were prepared directly from secondary amines by a reliable method using an oxidizing task-specific ionic liquid, choline peroxydisulfate. The operational simplicity, high selectivity, and green reaction conditions, make this method efficient and practical.