54121-55-0Relevant articles and documents
Metal-free late-stage C(sp2)-H functionalization of: N -aryl amines with various sodium salts
Mudithanapelli, Chandrashekar,Kim, Mi-Hyun
, p. 450 - 464 (2020/02/03)
Metal-free consecutive C(sp2)-X (X = Cl, Br, S, N) bond formations of N-aryl amines (cyclic, fused, carbamate, and aminium radicals) were achieved under mild conditions using [bis(trifluoroacetoxy)iodo]benzene (PIFA) and simple nonharmful sodium salts. This direct and selective C(sp2)-H functionalization showed excellent functional group compatibility, cost effectiveness, and late-stage applicability for the synthesis of biologically active natural products. Two mechanisms were proposed to explain the ortho- or para-preference, as well as the accelerating effect of CH3NO2
Halogenase-Inspired Oxidative Chlorination Using Flavin Photocatalysis
Hering, Thea,Mühldorf, Bernd,Wolf, Robert,K?nig, Burkhard
supporting information, p. 5342 - 5345 (2016/04/26)
Chlorine gas or electropositive chlorine reagents are used to prepare chlorinated aromatic compounds, which are found in pharmaceuticals, agrochemicals, and polymers, and serve as synthetic precursors for metal-catalyzed cross-couplings. Nature chlorinates with chloride anions, FAD-dependent halogenases, and O2 as the oxidant. A photocatalytic oxidative chlorination is described based on the organic dye riboflavin tetraacetate mimicking the enzymatic process. The chemical process allows within the suitable arene redox potential window a broader substrate scope compared to the specific activation in the enzymatic binding pocket. Chlorination of arenes with chloride anions: The photochemical analogue of the enzymatic chlorination of Flavin-adenine dinucleotide (FAD)-dependent halogenases is possible in the presence of riboflavin, air, acetic acid, and blue light (see scheme; RFT=riboflavin tetraacetate).
Synthesis of N-arylsubstituted pyrrolidines and piperidines by reaction of anilines with α,ω-diols catalyzed by FeCl3·6H2O in carbon tetrachloride
Khusnutdinov, Ravil I.,Bayguzina, Alfiya R.,Asylbaeva, Rigina S.,Aminov, Rishat I.,Dzhemilev, Usein M.
, p. 341 - 350 (2014/12/12)
N-Arylpyrrolidines and N-arylpiperidines were synthesized in 20-88% yields by the reaction of aniline and aniline derivatives with 1,4-butane- and 1,5-pentanediols in the presence of Fecontaining catalysts and carbon tetrachloride. 1,4-Butane- and 1,5-pentanediols are partially chlorinated under the reaction conditions to give chlorohydrins, which subsequently undergo Nheterocyclization with anilines to give N-arylpyrrolidines and N-arylpiperidines.
