17879-98-0

Upstream product

• 473-34-7 N,N-dichloro-p-toluenesulfonamide 
• 588-59-0 stilbene 
• 645-49-8 cis-stilben 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 127-65-1 chloroamine-T 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 40949-56-2 N-(p-toluenesulphonylimino)pyridinium ylide 
• 1058-14-6 N-p-tolylsulfonylphosphine imide 
• 1240327-54-1 2-(tert-butylsulfonyl)-5-tert-butyl-(tosyliminoiodo)benzene 
• 41085-71-6 bromamine T 

Downstream Products

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 93172-47-5 (+/-)-N-<1,2-diphenylethyl>toluene-p-sulfonamide 
• 124293-69-2 (2S,3R)-2,3-Diphenyl-1-(toluene-4-sulfonyl)-azetidine 

Relevant academic research and scientific papers

Regiodivergent and Stereospecific Aziridine Opening by Copper-Catalyzed Addition of Silicon Grignard Reagents

A stereospecific ring opening of various 2-aryl-substituted aziridines with silicon Grignard reagents under copper catalysis is reported. The regiochemical outcome is governed by the steric demand of the silicon nucleophile. The LiCl introduced with the m

Organocatalytic nitrenoid transfer: Metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt

This report details the first organocatalytic method for nitrenoid transfer and its application to intermolecular, site-selective C(sp3)-H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87%. A mechanistic proposal for the observed reactivity supported by experimental evidence invokes the intermediacy of a diaziridinium salt or related organic nitrenoid, species that have not been previously explored for the purpose of C-H amination. Finally, examples of late-stage functionalization of complex molecules highlight the selectivity and potential utility of this catalytic method in synthesis.

Branched Amine Synthesis via Aziridine or Azetidine Opening with Organotrifluoroborates by Cooperative Br?nsted/Lewis Acid Catalysis: An Acid-Dependent Divergent Mechanism

A practical catalytic method to synthesize β,β- and γ,γ-substituted amines by opening aziridines and azetidines, respectively, using alkenyl, alkynyl, or aryl/heteroaryl trifluoroborate salts is described. This reaction features simple open-flask reaction conditions, the use of transition-metal-free catalysis, complete regioselectivity, and high diastereoselectivity. Preliminary mechanistic studies suggest that carbocation formation is disfavored. Stereoretentive addition is favored with Br?nsted acid present, while stereoinversion is favored in its absence, indicating divergent mechanisms.

Alkene functionalization for the stereospecific synthesis of substituted aziridines by visible-light photoredox catalysis

A novel strategy involving visible-light-induced functionalization of alkenes for the synthesis of substituted aziridines was developed. The readily prepared N-protected 1-aminopyridinium salts were used for the generation of N-centered radicals. This approach allowed the synthesis of aziridines bearing various functional groups with excellent diastereoselectivity under mild conditions. Moreover, this protocol was successfully applied to prepare structurally diverse nitrogen-containing frameworks.

Grafting of copper(II) Schiff base complex on functionalized multi-wall carbon nanotubes: Synthesis, characterization and catalytic aziridination of olefins

In this study, hydroxyl functionalized copper(II) Schiff-base; [Cu((OH)2-salophen)], [(OH)2-salophen] = (N,N-bis(4-hydroxysalicylidene) phenylene-1,2-diamine); has been covalently anchored on modified multi-wall carbon nanotubes (MWN

Syntheses of a novel fluorinated trisphosphinoborate ligand and its copper and silver complexes. Catalytic activity toward nitrene transfer reactions

A novel fluorinated ligand, the anionic PhB(CH2P(p-CF 3C6H4)2)3 (PhBP 3 p-CF3Ph), has been synthesized and characterized, as well as its corresponding thallium, copper

Nanocrystalline zinc peroxide mediated unprecedented nitrene transfer: An expeditious access to N-tosylaziridines

An unprecedented zinc peroxide (ZnO2) assisted synthetic strategy is reported for the synthesis of N-tosylaziridines from alkenes by using N-tosyliminotriphenylphosphorane (Ph3PNTs) as a nitrene transfer reagent under mild reaction conditions. The reaction of zinc peroxide with Ph3PNTs yielded a zinc oxaziridine intermediate which subsequently reacts with alkenes to give corresponding N-tosylaziridines in high to excellent yields. The Royal Society of Chemistry 2013.

Metal-free aziridination of styrene derivatives with iminoiodinane catalyzed by a combination of iodine and ammonium iodide

The metal-free catalytic aziridination of styrene derivatives with N-tosyliminophenyliodinane (PhI=NTs) in the presence of a combination of I 2 and tetrabutylammonium iodide (TBAI) is reported. In situ generated TBAI3 from I2/s

Nickel-catalyzed negishi alkylations of styrenyl aziridines

A nickel-catalyzed cross-coupling reaction between N-sulfonyl aziridines and organozinc reagents is reported. The catalytic system comprises an inexpensive and air-stable Ni(II) source and dimethyl fumarate as ligand. Regioselective synthesis of β-substituted amines is possible under mild and functional-group-tolerant conditions. The stereoselectivity of the reaction is consistent with a stereoconvergent mechanism wherein the sulfonamide directs C-C bond formation.

Sulfur ylide promoted synthesis of N-protected aziridines: A combined experimental and computational approach

A range of N-protected aziridines [N-Tosyl (N-Ts), N-2- trimethylsilylethanesulfonamide (N-SES), N-tertbutoxycarbonylamido (N-Boc), and N-o-nitrobenzenesulfonamide (oNs)] were prepared in moderate to good yield and with high enantiomeric excess of both isomers starting from N-protected imines, using a sulfonium salt derived from Eliel's oxathiane. The diastereoselectivities of the reactions are influenced by the imine N-protecting group, the imine substituent, and the sulfide structure. An unusual cis selectivity was observed in the formation of N-tosyl-2-phenyl-3-tert- butylaziridine and N-o-trimethylsilylethanesulfonamide-2-phenyl-3-tert- butylaziridine, which was explained by using computational models. The analysis suggests that betaine formation in the case of N-tosyl-tert-butylaldimine aziridination using oxathiane benzyl sulfonium ylide 1′ is reversible and that the selectivity is determined at the rotation step, which is unusual for semistabilized ylide aziridination. We have shown herein that the steric bulk of an imine substituent, in combination with a sterically demanding sulfonium ylide, can also affect the reversibility of the reaction. This is the first example of this sort involving aziridinations using semistabilized ylides.