413188-48-4

Upstream product

• 591-80-0 pent-4-enoic acid 
• 4083-64-1 Tosyl isocyanate 
• 2100-17-6 4-pentenal 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 70-55-3 toluene-4-sulfonamide 
• 7103-09-5 4-but-1-enylmagnesium bromide 

Downstream Products

• 807332-17-8 5-(bromomethyl)-1-tosylpyrrolidin-2-one 
• 96013-62-6 5-methyl-1-tosyl-1,5-dihydro-2H-pyrrol-2-one 
• 118429-46-2 1-(4-methylphenyl)sulfonyl-5-methyl-2-pyrrolidinone 
• 81097-24-7 N-tosyl-(4-pentenyl)amine 
• 1011246-92-6 2-benzyl-1-(toluene-4-sulfonyl)pyrrolidine 
• 1070799-41-5 C₁₈H₂₁NO₂S 
• 96013-55-7 1-[(4-methylphenyl)sulfonyl]-5,6-dihydro-1H-piperidin-2-one 
• 1310538-47-6 1-tosyl-5-(3-(triisopropylsilyl)prop-2-ynyl)pyrrolidin-2-one 
• 1310538-49-8 5-(3-phenylprop-2-ynyl)-1-tosylpyrrolidin-2-one 
• 1310538-48-7 1-tosyl-5-(3-(trimethylsilyl)prop-2-ynyl)pyrrolidin-2-one 
• 1269774-76-6 1-(4-methylphenylsulfonyl)-5-nitromethylpyrrolidin-2-one 

Relevant academic research and scientific papers

Anti-Markovnikov Hydroazidation of Alkenes by Visible-Light Photoredox Catalysis

The anti-Markovnikov hydroazidation of alkenes has been accomplished under visible-light irradiation by using [Ir(dF(CF3)ppy)2(dtbbpy)]PF6 as the photocatalyst and trimethylsilyl azide as the azidating agent. The reactions were greatly facilitated by water, the beneficial effect of which can be attributed to its participation in the reaction as the hydrogen donor, as indicated by deuterium isotope experiments. The reactions proceed under solvent free conditions in the presence of water. 4-Dimethylaminopyridine also exhibited a beneficial effect on the reactions. The present method enabled hydroazidation of several types of unactivated alkenes with good yields and high regioselectivity.

Iridium-Catalyzed Intramolecular Oxidative Cyclization of Alkenyl Amides and Alkenoic Acids

An iridium/dppf complex efficiently catalyzed the oxidative cyclization of N sulfonyl alkenyl amides and alkenoic acids. Electron deficiena?t alkenes were effective as sacrificial hydrogen acceptors. High selectivity of the oxidative cyclization over the

Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles

Modified reaction conditions that facilitate Pd-catalyzed alkene carboamination reactions of electron-deficient nitrogen nucleophiles are reported. Pent-4-enylamine derivatives bearing N-tosyl or N-trifluoroacetyl groups are coupled with aryl triflates to

Dormant versus evolving aminopalladated intermediates: Toward a unified mechanistic scenario in PdII-catalyzed aminations

PdII-catalyzed alkene aminopalladation and allylic Ci￡H activation are two competing reaction sequences sharing the same reaction conditions. This study aimed at understanding the factors that bias one or the other path in the intramolecular oxidative cyclization of two types of N-tosyl amidoalkenes. The results obtained are in accord with the initial generation of a high-energy cyclic (5- or 6-membered) aminopalladated intermediate. However, this latter species can evolve only if the following specific conditions are met: the availability of distocyclic β-H elimination pathway, the presence of a strong terminal oxidant, or the availability of a carbopalladation pathway. Conversely, the cyclic alkylpalladium complex is only a latent species in equilibrium with the initial substrate and cannot evolve. Such a reactivity hurdle leaves the way open for alternative reactivities such as allylic Ci￡H activation of the olefinic substrate to generate a η3-allyl complex followed by its interception by the nitrogen nucleophile, [3,3]-sigmatropic rearrangement, or decomposition. This study proposes a unifying mechanistic picture that connects these competing mechanisms. Asleep or awake? Unsaturated N nucleophiles react through two competing pathways under PdII catalysis: Ci￡H allylic activation and aminopalladation. New data are in accord with the initial generation of a high-energy cyclic aminopalladated intermediate (API) that can either evolve along different pathways such as β-H elimination, oxidation, or carbopalladation, or lay dormant, the latter leading to alternative types of reactivity, such as allylic Ci￡H activation or [3,3]-sigmatropic rearrangement, gaining the upper hand (see scheme; Ts=p-toluenesulfonyl). Copyright

One-pot synthesis of N-heterocycles by tandem carbamoylation-oxidative bromolactamization of ω-alkenylmagnesium bromide

An addition reaction of ω-alkenylmagnesium bromide with p-toluenesulfonyl isocyanate and consecutive oxidative cyclization with iodobenzene diacetate afforded brominated lactams in one-pot. An imine was also applicable to a one-pot synthesis of terminally brominated cyclic amine.

A palladium-catalyzed aminoalkynylation strategy towards bicyclic heterocycles: Synthesis of (±)-trachelanthamidine

Sweet cyclizations: The synthesis of pyrrolizidines and indolizidines has been achieved. Olefins were subjected to an intramolecular palladium-catalyzed aminoalkynylation with the hypervalent iodine reagent TIPS-EBX. After removal of the protecting group, a two-step cyclization sequence and subsequent reduction led to the natural product (±)-trachelanthamidine (see scheme; TIPS-EBX=triisopropylsilyl ethynylbenziodoxolone).

Highly efficient ruthenium(II) porphyrin catalyzed amidation of aldehydes

H to N: The first example of a mild, highly efficient C-H bond amidation catalyzed by ruthenium(II) porphyrin complexes uses PhI=NTs as the nitrogen source for installing the amide bond functionality in a wide variety of aldehydes (see scheme). The protocol is chemoselective, with the new C-N bond forming only at the acyl C-H bond, even in aldehyde substrates containing other functional groups.

The tandem Heck-allylic substitution reaction: a novel route to lactams.

[reaction: see text] A novel route to substituted lactams has been developed using a tandem Heck-allylic substitution reaction. The palladium-catalyzed reaction between omega-olefinic N-tosyl amides and vinylic bromides affords in one step the substituted