55962-05-5

Usage

Uses

Used in Organic Synthesis:
PhI=NTs is used as an oxidizing agent for the conversion of alcohols to aldehydes or ketones, enabling the functionalization and modification of organic compounds. Its mild reaction conditions and high selectivity make it a preferred choice in synthetic chemistry for the development of complex organic molecules.
Used in Pharmaceutical Industry:
PhI=NTs is used as a reagent in the synthesis of pharmaceutical compounds, facilitating the conversion of alcohols to aldehydes or ketones, which are essential steps in the production of various drugs and medicinal agents.
Used in Chemical Research:
PhI=NTs is used as a research tool in chemical laboratories for studying the oxidation of alcohols and the development of new synthetic methods and techniques in organic chemistry. Its unique structure and reactivity provide valuable insights into the mechanisms of oxidation reactions and the design of novel synthetic pathways.

Upstream product

• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 70-55-3 toluene-4-sulfonamide 
• 85083-59-6 iodobenzene dimethoxide 
• 591-50-4 iodobenzene 
• 536-80-1 iodosylbenzene 

Downstream Products

• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 70-55-3 toluene-4-sulfonamide 
• 591-50-4 iodobenzene 
• 24395-14-0 (R)-2-phenyl-N-tosylaziridine 
• 24395-14-0 (S)-N-(p-tolylsulfonyl)-2-phenylaziridine 
• 4948-76-9 3-Tosyl-3-aza-tricyclo(3.2.1.0^2.4-exo)octan 
• 97401-93-9 N-(p-toluenesulfonyl)-2-(4-chlorophenyl)aziridine 
• 155721-36-1 2-(4-methoxyphenyl)-1-tosylaziridine 
• 94286-08-5 N-(p-toluenesulfonyl)-2,2-diphenylaziridine 
• 57981-16-5 N-(1-propyl-allyl)-4-methyl-benzenesulfonamide 
• 116905-61-4 2-butyl-N-tosylaziridine 
• 105882-02-8 N-[(2E)-hex-2-en-1-yl]-4-methylbenzene-1-sulfonamide 
• 97401-87-1 N-tosyl-2-(p-tolyl)aziridine 
• 146041-79-4 9-(toluene-4-sulfonyl)-9-aza-bicyclo[6.1.0]nonane 

Relevant academic research and scientific papers

Mechanistic studies of copper-catalyzed alkene aziridination

The mechanism of the copper-catalyzed aziridination of alkenes using [N-(p-toluenesulfonyl)imino]-phenyliodinane (PhINTs) as the nitrene source has been elucidated by a combination of hybrid density functional theory calculations (B3LYP) and kinetic exper

Method for preparing azabicyclic compounds

The method comprises the following steps: a compound of the formula II and a compound of the formula III react under the action of a Lewis acid [3 + 2], the azabicyclic compound represented by the formula I is obtained, and the reaction formula is as shown below. The method has the advantages of wide substrate adaptability range, mild reaction conditions, less reaction steps, high atom economy, high yield and stereoselectivity and the like.

Synthesis of Diverse Aryliodine(III) Reagents by Anodic Oxidation?

An anodic oxidation enabled synthesis of hypervalent iodine(III) reagents from aryl iodides is demonstrated. Under mild electrochemical conditions, a range of aryliodine(III) reagents including iodosylarenes, (difunctionaliodo)arenes, benziodoxoles and diaryliodonium salts can be efficiently synthesized and derivatized in good to excellent yields with high selectivity. As only electrons serve as the oxidation reagents, this method offers a more straightforward and sustainable manner avoiding the use of expensive or hazardous chemical oxidants.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea

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.

Expedient Synthesis of 2-Iminothiazolidines via Telescoping Reactions Including Iron-Catalyzed Nitrene Transfer and Domino Ring-Opening Cyclization (DROC)

2-iminothiazolidines are important scaffold for pharmaceutical drugs. Herein, we describe a fast and easy procedure for their synthesis by a telescoping reaction integrating an iron-catalyzed nitrene transfer under mild conditions. The aziridination react

Imidazoline synthesis: Mechanistic investigations show that Fe catalysts promote a new multicomponent redox reaction

Multicomponent reactions are attracting strong interest because they contribute to develop more efficient synthetic chemistry. Understanding their mechanism at the molecular level is thus an important issue to optimize their operation. The development of

HKUST-1 Metal Organic Framework as an Efficient Dual-Function Catalyst: Aziridination and One-Pot Ring-Opening Transformation for Formation of β-Aryl Sulfonamides with C-C, C-N, C-S, and C-O Bonds

Metal-organic frameworks (MOFs) are extensively used in catalysis due to their robust structure, well-defined periodic reaction centers, and high porosity. We report Cu3(BTC)2·(H2O)3 (HKUST-1) as an efficient heterogeneous catalyst for aziridination of al

Ligand Redox Noninnocence in [CoIII(TAML)]0/- Complexes Affects Nitrene Formation

The redox noninnocence of the TAML scaffold in cobalt-TAML (tetra-amido macrocyclic ligand) complexes has been under debate since 2006. In this work, we demonstrate with a variety of spectroscopic measurements that the TAML backbone in the anionic complex [CoIII(TAMLred)]- is truly redox noninnocent and that one-electron oxidation affords [CoIII(TAMLsq)]. Multireference (CASSCF) calculations show that the electronic structure of [CoIII(TAMLsq)] is best described as an intermediate spin (S = 1) cobalt(III) center that is antiferromagnetically coupled to a ligand-centered radical, affording an overall doublet (S = 1/2) ground-state. Reaction of the cobalt(III)-TAML complexes with PhINNs as a nitrene precursor leads to TAML-centered oxidation and produces nitrene radical complexes without oxidation of the metal ion. The ligand redox state (TAMLred or TAMLsq) determines whether mono-or bis-nitrene radical complexes are formed. Reaction of [CoIII(TAMLsq)] or [CoIII(TAMLred)]- with PhINNs results in the formation of [CoIII(TAMLq)(Na￠Ns)] and [CoIII(TAMLq)(Na￠Ns)2]-, respectively. Herein, ligand-to-substrate single-electron transfer results in one-electron-reduced Fischer-type nitrene radicals (Na￠Ns-) that are intermediates in catalytic nitrene transfer to styrene. These nitrene radical species were characterized by EPR, XANES, and UV-vis spectroscopy, high-resolution mass spectrometry, magnetic moment measurements, and supporting CASSCF calculations.

Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight

Olefin aziridination via organocatalytic nitrene transfer offers potential complementarity to metal-catalyzed methods; however there is a lack of reports of such reactions in the literature. Herein is reported a method that employs an iminium salt to cata