148961-16-4

Upstream product

• 111-66-0 oct-1-ene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 127-65-1 chloroamine-T 
• 592-41-6 1-hexene 
• 70-55-3 toluene-4-sulfonamide 
• 1338062-05-7 4-methyl-N-[(2-propoxyphenyl)-λ³-iodanylidene]benzenesulfonamide 
• 1058-14-6 N-p-tolylsulfonylphosphine imide 
• 98-59-9 p-toluenesulfonyl chloride 
• 1593-60-8 p-toluenesulfonylhydroxylamine 
• 41085-71-6 bromamine T 
• 21849-40-1 dibromamine-T 
• 124-38-9 carbon dioxide 
• 2984-50-1 1,2-Epoxyoctane 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 

Downstream Products

• 206361-00-4 4-Methyl-N-(1-phenylselanylmethyl-heptyl)-benzenesulfonamide 

Relevant academic research and scientific papers

Ring opening and expansion of aziridines in a silica-water reaction medium

Ring-opening reactions of N-tosylaziridines with water-soluble nucleophiles proceeded in a silica-water reaction medium. The system is applicable to a ring expansion of an aziridine with potassium thiocyanate, leading to a thiazolidine derivative.

Novel organic-solvent-free aziridination of olefins: Chloramine-T-I2 system under phase-transfer catalysis conditions

A variety of olefins could be aziridinated successfully by employing iodine-catalysed aziridination in water with a catalytic amount of a quaternary ammonium salt. Furthermore, the larger-scale process of styrene aziridination gives a highly pure aziridin

Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources

The iron-catalyzed intermolecular aziridination of alkenes with hydroxylamine derivatives is described. Using simple iron(ii) sources and readily available ligands, the formal (2 + 1) cycloaddition process proved to be efficient on both styrenes and aliphatic alkenes, providing access to a wide range of aziridines. In these particularly sustainable reaction conditions, yields up to 89% could be obtained, with a catalyst loading which could be lowered to 5 mol% when the reaction was performed on large scale. Preliminary mechanistic studies suggest that both concerted and stepwise pathways are operating in this transformation. This journal is

Ni-Catalyzed Carboxylation of Aziridines en Route to β-Amino Acids

A Ni-catalyzed reductive carboxylation of N-substituted aziridines with CO2 at atmospheric pressure is disclosed. The protocol is characterized by its mild conditions, experimental ease, and exquisite chemo- and regioselectivity pattern, thus unlocking a new catalytic blueprint to access β-amino acids, important building blocks with considerable potential as peptidomimetics.

Transition-Metal-Free Stereospecific Oxidative Annulative Coupling of Indolines with Aziridines

Tandem C-N bond formation for the oxidative annulation of indolines with aziridines is accomplished employing the combination of DDQ and NaOCl at ambient conditions. Optically active aziridine can be coupled with high enantiomeric purity (>99% ee). The substrate scope, stereocontrol with the enantioenriched substrate, and scale-up are the important practical advantages.

A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: Catalytic olefin aziridination reactions

A bromo-capped metal-metal bonded diruthenium(i,i) complex Ru2(CO)4(PIN)2Br2 (1) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with N-bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiometric reactions with 1 and NBS. An analysis of the dibrominated products suggests the formation of cyclic bromonium intermediates indicating in situ Br2 generation. Complex 2, an iodide analogue of 1, is also synthesized. The reaction of 2 with N-iodosuccinimide releases I2, which is confirmed by the starch-iodine test. The catalytic utility of 1 is examined for the bromination of phenol. Catalyst 1, in combination with NBS and base, exhibits regioselectivity towards monobrominated products. Furthermore, efficient olefin aziridination is demonstrated utilizing catalyst 1 in the presence of NBS, K2CO3 and TsNH2.

Stereospecific copper-catalyzed domino ring opening and sp3 C-H functionalization of activated aziridines with N-alkylanilines

Copper efficiently catalyzed nucleophilic ring opening, sp3 C-H functionalization, and C-N bond formation in the presence of tert-butyl hydroperoxide to afford functionalized imidazolidines starting from N-sulfonylaziridines and Nalkylanilines. The products were obtained in high optical purities (95 → 99% ee) with excellent functional group tolerance.

Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions

We developed an efficient fluorination protocol that converts easily accessible aziridines into β-fluoroamines, which are important motifs in biologically active molecules. In contrast with traditional fluorination approaches, DMPU-HF has shown both highe

Aziridination of olefins with bromamine-T in presence of iodine as catalyst

A strategy for achieving synthesis of aziridine employing iodine catalysed aziridination of alkenes with bromamine-T as nitrene source has been described. Ethyl acetate has been found to be the most suitable solvent and the strategy has been extended to v

Scalable synthesis of N -acylaziridines from N -tosylaziridines

N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N