136573-40-5

Upstream product

• 136573-35-8 N-<2-(Phenylseleno)ethyl>-p-toluenesulfonamide 
• 106-95-6 allyl bromide 
• 40596-30-3 (E)-1-chloro-2,4-pentadiene 
• 70-55-3 toluene-4-sulfonamide 
• 4083-64-1 Tosyl isocyanate 
• 98-59-9 p-toluenesulfonyl chloride 
• 1001919-18-1 (±)-1-tosyl-1,2,3,6-tetrahydropyridin-3-ol 
• 922-65-6 divinylcarbinol 
• 211814-64-1 5-[N-(4-methylphenylsulfonyl)amino]penta-1,2-diene 

Downstream Products

• 705962-76-1 4-methyl-N-[(2E)-2-methylpenta-2,4-dienyl]-N-[(2E)-penta-2,4-dienyl]benzenesulfonamide 
• 478176-04-4 N-[(2E,4)-pentadienyl]-N-(3-penytnyl)-p-toluenesulfonamide 
• 705963-10-6 (3R,4R)-3-((E)-But-1-enyl)-4-((S)-1-methoxymethyl-allyl)-3-methyl-1-(toluene-4-sulfonyl)-pyrrolidine 
• 705962-77-2 methyl (2S)-2-{(3R,4R)-4-[(1E)-but-1-enyl]-4-methyl-1-(4-methylbenzenesulfonyl)pyrrolidin-3-yl}but-3-enoate 
• 1011534-25-0 N-(3-cyclopentylideneprop-2-en-1-yl)-N-[(2E)-penta-2,4-dien-1-yl]-N-toluenesulfonamide 
• 1152437-69-8 (E)-4-methyl-N-(4-methylpenta-2,3-dien-1-yl)-N-(penta-2,4-dien-1-yl)benzenesulfonamide 
• 1304145-44-5 (E)-4-methyl-N-(2-methylbuta-2,3-dien-1-yl)-N-(penta-2,4-dien-1-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Asymmetric palladium-catalyzed allylic alkylation using dialkylzinc reagents: A remarkable ligand effect

A serendipitously discovered palladium-catalyzed asymmetric allylic alkylation reaction with diorganozinc reagents, which displays broad functional group compatibility, is reported. This novel transformation hinges on a remarkable ligand effect which overrides the standard "umpolung" reactivity of allyl-palladium intermediates in the presence of dialkylzincs. Owing to its mild conditions, enantioselective allylic alkylations of racemic allylic electrophiles are possible in the presence of sensitive functional groups. Umpole-me-not: A serendipitously discovered palladium-catalyzed asymmetric allylic alkylation reaction with diorganozinc reagents displays broad functional group compatibility. This novel transformation hinges on a remarkable ligand effect which overrides the standard "umpolung" reactivity of allyl-palladium intermediates in the presence of dialkylzinc compounds.

FeCl3·6H2O and TfOH as catalysts for allylic amination reaction: A comparative study

The use of FeCl3·6H2O and TfOH as readily available and easy-to-handle catalysts for the direct allylic amination reaction using a wide variety of nitrogenated nucleophiles onto different free allylic alcohols is described. Comparative studies between these catalysts, as representative Lewis and Bronsted acids are conducted, concluding that both are suitable catalysts for this transformation. The reactions are performed in a flask open to air and using technical grade 1,4-dioxane. In light of the results obtained from this study it can be asserted that TfOH turned out to be slightly superior than the FeIII salt since similar or better yields are obtained in most of the cases using lower catalyst loadings and milder reaction conditions. A similar trend is observed when carbonucleophiles were employed in the allylic substitution reaction. Studies for the elucidation of the reaction mechanism are in agreement with a carbocationic intermediate, being the regioselectivity governed by the stability of the final product. Copyright

Gold versus silver-catalyzed amination of allylic alcohols

Direct substitution of the hydroxy group in allylic alcohols by different nitrogenated nucleophiles is performed using low loadings of cationic gold(I) or silver salts as catalysts. Sulfonamides, carbamates and aromatic amines can be used as nucleophiles. Comparative studies between the best catalysts, cationic (triphenylphosphite)gold(I) complex and silver triflate, demonstrate that the former catalyst shows, in general, better performance than silver, working at lower loadings, in shorter reaction times and at lower temperatures. Representative allylic alcohols are used giving good γ-regioselectivity, specially in the case of penta-1,4-dien-3-ol and (E)-1-phenylbut-2-en-1-ol affording the corresponding allylic sulfonamides with total regio and stereoselectivity by a hydroamination mechanism. In the case of crotyl alcohol and (E)-4-phenylbut-3-en-2-ol mainly and exclusively α-substituted sulfonamides were obtained, respectively, by a cationic mechanism.

Gold(I)-catalyzed highly regio- and stereoselective decarboxylative amination of allylic N-tosylcarbamates via base-induced aza-Claisen rearrangement in water

(Figure Presented)A gold(l)-catalyzed decarboxylative animation of allylic N-tosylcarbamates via base-induced aza-Claisen rearrangement has been developed. A variety of substituted W-tosyl allylic amines were obtained In good yield, excellent regloselectlvity, and high to excellent stereoselectivity. This transformation could be performed either in H2O or In one pot directly from allylic alcohols and therefore represents an efficient and environmentally benign protocol for the synthesis of N-tosyl allylic amines.

Nickel-catalyzed addition of dimethylzinc to aldehydes across alkynes and 1,3-butadiene: An efficient four-component connection reaction

In the presence of 10 mol % of Ni(acac)2, four components comprising Me2Zn, alkynes, 1,3-butadiene, and carbonyl compounds combine in this order in 1:1:1:1 ratio to furnish (3E,6Z)-octadien-1-ols 1 in good yields. Similarly, the coupling reaction of Me2Zn, 1,ω-dienynes 5, and carbonyls furnishes 1-alkylidene-2-(4′-hydroxy- (1′E)-alkenyl)cyclopentanes and -cyclohexanes 6 and their oxygen and nitrogen heterocycle derivatives in good yield and an excellent level of 1,5-diastereoselectivity with respect to the cycloalkane methine carbon and the OH-bearing carbon of the C2 side chain. The reaction is completed in most cases within 1 h at room temperature under nitrogen, tolerates an ester, a hydroxy, an allyl and propargyl ethers, an allylamino, and a pyridyl functionalities, and accommodates a variety of aromatic and aliphatic alkynes and carbonyls (aldehydes and ketones).

A facile highly regio- and stereoselective preparation of N-tosyl allylic amines from allylic alcohols and tosyl isocyanate via palladium(II)-catalyzed aminopalladation-β-heteroatom elimination

(equation presented) The high regio- and stereoselectivity have been obtained from the allylic substitution reaction catalyzed by palladium(II) species. From allylic alcohols, one-pot reaction with tosyl isocyanate followed by palladium(II)-catalyzed ally

A new method for the synthesis of nitrogen heterocycles via palladium catalyzed intramolecular hydroamination of allenes

The intramolecular hydroamination of certain allenes, beating amine or sulfonyl amide groups at the terminus of the carbon chain, proceeded smoothly in the presence of catalytic amounts of palladium complex ([(η3- C3H5)PdC

Amidoselenation of Olefins Using p-Toluenesulfonamide as a Nitrogen Nucleophile

The reaction of olefins, benzeneselenenyl chloride, and p-toluenesulfonamide in the presence of zinc(II) chloride affords N--p-toluenesulfonamides in good to excellent yields.When combined with alkylation on the carbon atom bearing the phenylseleno group thus introduced and subsequent oxidative or reductive removal of the selenium moiety, this reaction can be utilized in the preparation of a wide range of allylic or saturated amides.