154139-38-5

Upstream product

• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 75-36-5 acetyl chloride 
• 1888-33-1 N-acetyl-(4-methylbenzene)sulfonamide 
• 106-95-6 allyl bromide 
• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-24-7 acetic anhydride 
• 154139-24-9 N-allyl-N-(2-bromo-acetyl)-4-methyl-benzenesulfonamide 

Downstream Products

• 851461-11-5 dithiocarbonic acid O-ethyl ester S-[1-(N-acetyl-N-(4-toluenesulfonyl)aminomethyl)-4-oxo-4-phenylbutyl] ester 
• 946076-29-5 dithiocarbonic acid O-ethyl ester S-[1-(N-acetyl-N-(4-toluenesulfonyl)aminomethyl)-4-oxopentyl] ester 
• 851461-04-6 5-[acetyl(toluene-4-sulfonyl)amino]4-ethoxythiocarbonylsulfanylpentanoic acid methyl ester 
• 851461-20-6 N-(5-oxo-5-phenyl-2-p-tolylpentyl)acetamide 
• 851461-13-7 5-acetylamino-4-p-toluenepentanoic acid methyl ester 

Relevant academic research and scientific papers

NIS-mediated ring-closure/opening cascade reactions of allylamides: An expedient route to oxazolines

An unprecedented NIS-mediated ring-closure/opening cascade reaction of allylamides is developed. The substrates with various functionalities were well tolerated and the scope can be extended to allylic carboxylates. Notably, the resulting iodinated chain

Alkene Carboarylation through Catalyst-Free, Visible Light-Mediated Smiles Rearrangement

A light-mediated Truce–Smiles arylative rearrangement is described that proceeds in the absence of any photocatalyst. The protocol creates two C?C bonds from simple starting materials, with the installation of an aryl ring and a difluoroacetate moiety across unactivated alkenes. The reaction proceeds via a radical mechanism, utilizing a light-mediated reduction of ethyl bromodifluoroacetate by N,N,N′,N′-tetramethylethylenediamine (TMEDA) to set up intermolecular addition to an unactivated alkene, followed by Truce–Smiles rearrangement.

Radical reductions of alkyl halides bearing electron withdrawing groups with N-heterocyclic carbene boranes

1,3-Dimethylimidazol-2-ylidene borane and 2,4-dimethyl-1,2,4-triazol-3- ylidene borane are found to be useful reagents for the reduction of alkyl iodides and bromides bearing nearby electron withdrawing substituents. Signatures of radical chain reactions are seen in many cases, but ionic reductions may also be occurring with some substrates. The reagents are attractive because of their low molecular weight, their availability from inexpensive precursors, and their stability. Separation of the borane products from the target products is readily accomplished either with or without prior regeneration of the borane for later reuse. 2,4-Dimethyl-1,2,4-triazol-3-ylidene borane is versatile because both starting borane and its derived products can be removed by extraction with water.

Synthesis of substituted 3-arylpiperidines and 3-arylpyrrolidines by radical 1,4 and 1,2-aryl migrations

A route to 3-arylpiperidines and 3-arylpyrrolidines involving radical 1,4- and 1,2-aryl migrations has been explored. For the piperidines, the first route requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with lauroyl peroxide to give the corresponding 1,4-aryl transfer product. This compound can be converted into the desired piperidine derivative following acidic hydrolysis. For the second approach to piperidines, addition of an α-keto xanthate to olefins of type 14 causes 1,2-aryl migration leading to an α,β-unsaturated ester, which can be converted into a piperidine by the action of ammonia or a primary amine and sodium cyanoborohydride. Substituted 3-arylpyrrolidines can be obtained by simply starting with an α-amido substituted xanthate.

Synthesis of 3-arylpiperidines by a radical 1,4-aryl migration

(Chemical Equation Presented) A route to 3-arylpiperidines, 3-arylpyridines, and 5-arylpiperidin-2-ones involving a radical 1,4-aryl migration has been explored. The sequence requires a xanthate addition to an N-allylarylsulfonamide, followed by acetylation and treatment with dilauroyl peroxide to give the 1,4-aryl transfer product, which upon acidic hydrolysis affords the desired piperidine derivative.

Indirect electroreductive cyclization of N-allyl and N-propargylamides using a nickel(II) complex as an electron-transfer catalyst: Selective formation of halogenated and non-halogenated pyrrolidinones

Nickel(II) complex-catalyzed indirect electroreduction of N-allyl and N-propargyl-α-bromoamides conducted in dimethylformamide with 2 eq of a hydrogen atom donor, diphenylphosphine, afforded the corresponding pyrrolidinones as the sole cyclized product in

Indirect Electroreductive Cyclisation of N-Allylic and N-Propargylbromo Amides and o-Bromoacryloylanilides using Nickel(II) Complexes as Electron-transfer Catalysts

Nickel(II) complex-catalysed indirect electroreduction of N-allylic and N-propargyl-α-bromo amides and o-bromoacryloylanilides gave the corresponding 5-membered lactams.The product distribution was affected by the ability of the solvent to donate hydrogen atom.The electroreduction of N-allyl-N-(bromoacetyl)toluene-p-sulfonamide 1a in DMF and acetonitrile yielded as main product the 4-methylpyrrolidinone 2a (41percent) and the 4-(bromomethyl)pyrrolidinone 3a (33percent), respectively.On addition of 2 mol equiv. of a hydrogen-atom donor (Ph2PH) to the reaction of bromo amide 1a in acetonitrile, compound 1a provided compound 2a (58percent) as the sole cylised product.