82998-19-4Relevant academic research and scientific papers
Three-Component Aminoarylation of Electron-Rich Alkenes by Merging Photoredox with Nickel Catalysis
Jiang, Heng,Yu, Xiaoye,Daniliuc, Constantin G.,Studer, Armido
, p. 14399 - 14404 (2021)
A three-component 1,2-aminoarylation of vinyl ethers, enamides, ene-carbamates and vinyl thioethers by synergistic photoredox and nickel catalysis is reported. 2,2,2-Trifluoroethoxy carbonyl protected α-amino-oxy acids are used as amidyl radical precursors. anti-Markovnikov addition of the amidyl radical to the alkene and Ni-mediated radical/transition metal cross over lead to the corresponding 1,2-aminoarylation product. The radical cascade, which can be conducted under practical and mild conditions, features high functional group tolerance and broad substrate scope. Stereoselective 1,2-aminoarylation is achieved using a L-(+)-lactic acid derived vinyl ether as the substrate, offering a novel route for the preparation of protected enantiopure α-arylated β-amino alcohols. In addition, 1,2-aminoacylation of vinyl ethers is achieved by using an acyl succinimide as the electrophile for the Ni-mediated radical coupling.
Iron(II)-Catalyzed Intermolecular Aminofluorination of Unfunctionalized Olefins Using Fluoride Ion
Lu, Deng-Fu,Zhu, Cheng-Liang,Sears, Jeffrey D.,Xu, Hao
supporting information, p. 11360 - 11367 (2016/10/12)
We herein report a new catalytic method for intermolecular olefin aminofluorination using earth-abundant iron catalysts and nucleophilic fluoride ion. This method tolerates a broad range of unfunctionalized olefins, especially nonstyrenyl olefins that are incompatible with existing olefin aminofluorination methods. This new iron-catalyzed process directly converts readily available olefins to internal vicinal fluoro carbamates with high regioselectivity (N vs F), many of which are difficult to prepare using known methods. Preliminary mechanistic studies demonstrate that it is possible to exert asymmetric induction using chiral iron catalysts and that both an iron-nitrenoid and carbocation species may be reactive intermediates.
A VERSATILE METHOD FOR PREPARATION OF O-ALKYLPEROXICARBONIC ACIDS: EPOXIDATION WITH ALKYLOXYCARBONYLIMIDAZOLES AND HYDROGEN PEROXIDE
Tsunokawa, Youko,Iwasaki, Shigeo,Okuda, Shigenobu
, p. 2113 - 2116 (2007/10/02)
A variety of O-alkylperoxycarbonic acids (2) were conveniently prepared in situ by utilizing alkyloxycarbonylimidazoles (1) as their precursors.Epoxidation of alkenes with such peroxy-acids was studied and their reactivities were compared with those of peroxycarboxylic acids.
