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 
• 106-95-6 allyl bromide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 120568-65-2 Acetic acid (E)-4-[allyl-(toluene-4-sulfonyl)-amino]-but-2-enyl ester 
• 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 
• 18303-03-2 prop-2-en-1-yl (4-methylbenzene-1-sulfonyl)carbamate 
• 21040-45-9 Cinnamyl acetate 

Downstream Products

• 129748-58-9 N-tosyl-N-(4-bromobutyl)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 
• 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 
• 83865-35-4 4-[N-(2-propenyl)-(4-toluenesulfonamido)]azetidin-2-one 
• 153391-78-7 (Z)-N-{4-[(methoxycarbonyl)oxy]but-2-enyl}-N-(prop-2-enyl)-p-toluenesulfonamide 
• 106003-71-8 N-allyl-N'-(2,7-octadienyl)-p-toluenesulfamide 
• 129748-56-7 N-(2-bromoethyl)-N-(2-propenyl)-4-methylbenzenesulfonamide 
• 129748-57-8 N-allyl-N-(3-bromopropyl)-4-methylbenzenesulfonamide 
• 167029-87-0 N-allyl-N-(2-bromo-propionyl)-4-methyl-benzenesulfonamide 

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.

Copper(I)-Catalyzed Enyne Oxidation/Cyclopropanation: Divergent and Enantioselective Synthesis of Cyclopropanes

An efficient copper(I)-catalyzed enyne oxidation/cyclopropanation for the modular synthesis of cyclopropane derivatives is described, which represents the first non-noble metal-catalyzed enynes oxidation/cyclopropanation by the in situ generated α-oxo copper carbenes. This protocol allows the assembly of valuable cyclopropane-γ-lactams in generally good to excellent yields with excellent diastereoselectivity. More significantly, the enantioselective version of enyne oxidation/cyclopropanation has been disclosed with chiral copper catalysts.

Practical Synthesis of Halogenated N-Heterocycles via Electrochemical Anodic Oxidation of Unactivated Alkenes

A general and efficient intramolecular halo-amination of unactivated alkenes for the synthesis of various halogenated N-heterocycles was developed via electrochemical anodic oxidation. This protocol proceeds in a simple undivided cell by employing LiI or LiBr as redox mediums and halogen sources. A wide range of halogenated N-heterocycles, including three-, five-, and six-membered N-heterocycles were constructed in moderate to good yields at room temperature. Notably, this electrochemical oxidative transformation avoids the utilization of external oxidants and strong bases, therefore represents an environmentally benign approach.

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

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

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