146041-79-4Relevant articles and documents
Palladium-catalyzed aziridination of alkenes using N,N-dichloro-p-toluenesulfonamide as nitrogen source
Han, Jianlin,Li, Yufeng,Zhi, Sanjun,Pan, Yi,Timmons, Cody,Li, Guigen
, p. 7225 - 7228 (2006)
N,N-Dichloro-p-toluenesulfonamide (TsNCl2) was found to be an efficient nitrogen source for the aziridination of unfunctionalized alkenes using palladium catalysts. Among the palladium salts, palladium acetate was the most effective catalyst for this reaction. A variety of alkenes were reacted at room temperature with TsNCl2 to form the desired aziridines in moderate to good yields. This method can complement our previous protocol which is limited to the use of electron-deficient α,β-unsaturated alkenes.
Efficient copper-catalyzed benzylic amidation with anhydrous chloramine-T
Bhuyan, Ranjana,Nicholas, Kenneth M.
, p. 3957 - 3959 (2007)
Benzylic hydrocarbons are selectively converted to the corresponding sulfonamides by the [Cu(CH3CN)4]PF6-catalyzed reaction with anhydrous TolSO2NNaCl (chloramine-T). Under the same conditions, representative ethers are also α-amidated; olefins produce allyl sulfonamides, aziridines, and/or β-chloro sulfonamides.
Formation of an Iron(III) Porphyrin Complex with a Nitrene Moiety Inserted into a Fe-N Bond during Alkene Aziridination by benzene Catalyzed by Iron(III) Porphyrins
Mahy, Jean-Pierre,Battioni, Pierrette,Mansuy, Daniel
, p. 1079 - 1080 (1986)
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Manganese-catalyzed aziridination of olefins with chloramine-T in water and buffered aqueous solutions
Wolgemuth, Daniel K.,Elmore, Sydnee D.,Cope, James D.,Sheridan, Patrick E.,Stokes, Sean L.,Emerson, Joseph P.
, (2021/01/04)
A water-soluble, manganese-porphyrin complex was used to catalytically generate aziridines from olefins in moderate to good yields (up to 93%) upon optimization at room temperature and in aqueous media. Reactions using chloramine-T at slightly acidic to n
An Electron-Poor Dioxa-[2.1.1]-(2,6)-pyridinophane Ligand and Its Application in Cu-Catalyzed Olefin Aziridination
Yang, Fan,Ruan, Jiaheng,Zavalij, Peter Y.,Vedernikov, Andrei N.
, (2019/11/14)
A novel macrocyclic 1,7-dioxa-[2.1.1]-(2,6)-pyridinophane ligand has been synthesized and crystallographically characterized. Two derived metal complexes, dichloropalladium(II) and chlorocopper(I), were prepared. In the palladium(II) complex LPdCl2/
Copper-Catalyzed Aziridination with Redox-Active Ligands: Molecular Spin Catalysis
Ren, Yufeng,Cheaib, Khaled,Jacquet, Jérémy,Vezin, Hervé,Fensterbank, Louis,Orio, Maylis,Blanchard, Sébastien,Desage-El Murr, Marine
, p. 5086 - 5090 (2018/02/21)
Small-molecule catalysts as mimics of biological systems illustrate the chemists’ attempts at emulating the tantalizing abilities displayed by nature's metalloenzymes. Among these innate behaviors, spin multistate reactivity is used by biological systems as it offers thermodynamic leverage towards challenging chemical reactivity but this concept is difficult to translate into the realm of synthetic organometallic catalysis. Here, we report a rare example of molecular spin catalysis involving multistate reactivity in a small-molecule biomimetic copper catalyst applied to aziridination. This behavior is supported by spin state flexibility enabled by the redox-active ligand.