50487-71-3

Usage

Uses

Used in Chemical Synthesis:
N-Allyl-4-methylbenzenesulfonamide is used as a catalyst in the process of ring-closing enyne metathesis when utilizing Grubbs I type catalysts. Its application is crucial for facilitating the formation of cyclic structures from enyne substrates, which are important in the synthesis of complex organic molecules and have potential applications in pharmaceuticals, materials science, and other related fields.

Synthesis Reference(s)

Tetrahedron Letters, 20, p. 623, 1979 DOI: 10.1016/S0040-4039(01)86019-6

InChI:InChI=1/C10H13NO2S/c1-3-8-11-14(12,13)10-6-4-9(2)5-7-10/h3-7,11H,1,8H2,2H3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 107-11-9 1-amino-2-propene 
• 591-87-7 Allyl acetate 
• 18522-92-4 sodium p-toluenesulfonamide 
• 1469-70-1 allyl ethyl carbonate 
• 70-55-3 toluene-4-sulfonamide 
• 106-95-6 allyl bromide 
• 120568-65-2 Acetic acid (E)-4-[allyl-(toluene-4-sulfonyl)-amino]-but-2-enyl ester 
• 169137-89-7 S-(prop-2-enyl)-S-phenyl-N-(p-tolylsulfonyl) sulfoximide 
• 941-55-9 4-toluenesulfonyl azide 
• 24850-33-7 allyltributylstanane 
• 76-63-1 allytriphenyltin 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 102654-50-2 N-(2,3-dibromopropyl)-4-methylbenzenesulfonamide 
• 56643-09-5 N,N'-Diallyl-N,N'-tetramethylen-bis-(p-toluolsulfonamid) 
• 66897-38-9 N-Allyl-N-(2,4-dichloro-benzoyl)-4-methyl-benzenesulfonamide 
• 129748-58-9 N-tosyl-N-(4-bromobutyl)allylamine 
• 2645-02-5 methyl tosylglycinate 
• 129748-59-0 N-tosyl-N-(5-bromopentyl)allylamine 
• 155088-02-1 N-allyl-N-tosyl-α,α-dichloroacetamide 
• 154139-26-1 N-allyl-N-tosyl-α,α-dimethyl-α-bromoacetamide 
• 154330-95-7 N-tosyl-α,α-dichloro-α-methyl-allylacetamide 
• 116043-28-8 N-Allyl-4-methyl-N-((E)-octa-2,7-dienyl)-benzenesulfonamide 
• 121224-75-7 Acetic acid (1R,4S)-4-[allyl-(toluene-4-sulfonyl)-amino]-cyclohex-2-enyl ester 
• 133886-44-9 2-(Toluene-4-sulfonyl)-hexahydro-cyclopenta[c]pyrrol-5-one 
• 133886-43-8 2,3,3a,4-tetrahydro-2-[(4-methylphenyl)sulfonyl]-cyclopenta[c]pyrrol-5(1H)-one 
• 134886-28-5 2,3,3a,4-tetrahydro-6-methyl-2-[(4-methylphenyl)sulfonyl]-cyclopenta[c]pyrrol-5(1H)-one 

Relevant academic research and scientific papers

Ligand geometry effects in copper mediated atom transfer radical cyclisations

The relative rate of copper (I) mediated atom transfer radical cyclisation of (11) with a range of ligands at room temperature has been screened. The most active ligands were found to be multidentate amine ligands (6-7).

Mechanistic studies of reactive oxygen species mediated electrochemical radical reactions of alkyl iodides

Mechanistic studies of a reactive oxygen species mediated electrochemical radical reaction of alkyl iodides are described. Hydroxyl radicals and ozone are identified to be the active species involved in the formation of alkyl radicals under mildly reducing potential (-1.0 V vs. Ag QRE) in buffered acidic conditions (pH 3.6).

Transformation of allylic silanes into allylic amines using [N-(P- toluenesulfonyl)imino]phenyliodinane

Reaction of allylic silanes with PhI=NTs in the presence of catalytic Cu(OTf)2 provides a direct route for the preparation of allylic amines in moderate yields.

Excited-State Copper Catalysis for the Synthesis of Heterocycles

Heterocycles are one of the largest groups of organic moieties with significant medicinal, chemical, and industrial applications. Herein, we report the discovery and development of visible-light-induced, synergistic excited-state copper catalysis using a combination of Cu(IPr)I as a catalyst and rac-BINAP as a ligand, which produces more than 10 distinct classes of heterocycles. The reaction tolerates a broad array of functional groups and complex molecular scaffolds, including derivatives of peptides, natural products, and marketed drugs. Preliminary mechanistic investigation suggests in situ generations of [Cu(BINAP)2]+ and [Cu(IPr)2]+ catalysts that work cooperatively under visible-light irradiation to facilitate catalytic carbo-aroylation of unactivated alkenes, affording a wide range of useful heterocycles.

A tandem process for the synthesis of β-aminoboronic acids from aziridines with haloamine intermediates

An unprecedented synthetic strategy is devised to generate β-aminoboronic acids from aziridines via a sequential process involving 1,2-iodoamine formation and radical borylation under light irradiation. A variety of aziridines including multiply substituted aziridines have been successfully employed as synthetic precursors, expanding their synthetic utility compared to previous methods. Mechanistic studies suggest that the boron source plays a unique role in the borylation step, and in the formation of haloamine intermediates.

Twofold Radical-Based Synthesis of N, C-Difunctionalized Bicyclo[1.1.1]pentanes

Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs; the newly formed C-I bond in these products is then functionalized via a silyl-mediated Giese reaction. This chemistry also translates smoothly to 1,3-disubstituted iodo-BCPs. A wide variety of radical acceptors and iodo-BCPAs are accommodated, providing straightforward access to an array of valuable aniline-like isosteres.

A Free Radical Cyclization Catalyzed by Ruthenium Hydride Species

A photolytically generated ruthenium hydride species catalyzing a free radical cyclization reaction was developed. As the new methodology ensures reproducibility of the free radical reaction of trialkyltin hydrides and a fast hydrogen transfer to the radical intermediates, the methodology provides fast quenching of radical intermediates and thus suppresses rearrangement of radical intermediates before the hydride quench. By offering new reactivity and selectivity to the trialkyltin hydride mediated free radical cyclization reactions, the methodology will find wide range of applications in organic synthesis.

Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications

Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.

Diastereodivergent Intermolecular 1,2-Diamination of Unactivated Alkenes Enabled by Iodine Catalysis

The stereospecific, substrate (nitrogen source)-controlled intermolecular anti-and syn-1,2-diaminations of unactivated alkenes using the same catalysis (an iodine catalyst) is reported. The combined use of the two potential methods provides access to all of the disastereomeric forms of 1,2-diamines in spite of the availability of E-and Z-Alkenes, and the resulting products can be readily converted into free vicinal diamines.

Recurrent Approximation of Retention Parameters of N-Substituted p-Toluenesulfonamides in Reversed-Phase High Performance Liquid Chromatography for Revealing the Formation of Their Hydrates

Abstract: Recurrent approximation of retention times in reversed-phase high performance liquid chromatography (RP-HPLC), tR(C + ΔC) = atR(C) + b, where C is the acetonitrile concentration in the eluent, and ΔC is the constant “step” of its variation, for six specially synthesized N-substituted p-toluenesulfonamides confirmed the presence of anomalies previously revealed for some complex polyfunctional organic compounds. The reason for these anomalies is the presence of sulfonamide –SO2–NH fragments in the molecules, which leads to hydration of sorbates in aqueous solutions, or, more precisely, to a change in the ratio of their non-hydrated and hydrated forms because of a shift in the equilibrium Х + Н2О $$ rightleftarrows $$ Х·Н2О (*) as a result of a change in the eluent composition. The same effect is indicated by the strong antibatic dependence of the retention indices RI(C) of all sulfonamides under study; the coefficients dRI/dC vary from –1.9 to –4.0, these values being much higher in magnitude than for compounds that do not form hydrates. Further independent evidence in favor of the transformation of sorbates due to variation of the eluent composition is the dependence of the relative absorbance Arel = A(254)/A(220) on the acetonitrile content in the eluent. This suggests changes in the chemical nature of chromophores in sulfonamide molecules depending on the equilibrium state (*).