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Upstream product

• 300-57-2 allylbenzene 
• 70-55-3 toluene-4-sulfonamide 
• 25856-77-3 1-tosyl-2-methylaziridine 
• 98-80-6 phenylboronic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 2706-50-5 amphetamine hydrochloride 
• 32343-98-9 n-butyl(phenyl)tellane 

Downstream Products

• 904246-40-8 N-(2-phenylethyl)-N-[(4-methylphenyl)sulfonyl]glycine methyl ester 
• 76553-22-5 Clobenzorex 

Relevant academic research and scientific papers

Atmosphere- and Temperature-Controlled Regioselective Aminobromination of Olefins

A complete switch of regioselectivity in the aminobromination of olefins is realized from delicate changes in the reaction temperature from 25 °C to 40 °C and the atmosphere from air to argon, under catalyst-free conditions. The resulting α-bromoamides ca

A Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines

Described is a new hydrazone-based exo-directing group (DG) strategy developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. Conveniently synthesized from protected primary amines, the hydrazone DGs are shown to site-selectively promote the β-acetoxylation and tosyloxylation via five-membered exo-palladacycles. Amines with a wide scope of skeletons and functional groups are tolerated. Moreover, the hydrazone DG can be readily removed, and a one-pot C-H acetoxylation/DG removal protocol was also discovered. All about the DGs: A hydrazone-based exo-directing group (DG) strategy is developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. The hydrazone DGs can be conveniently installed and removed, and promote β-acetoxylation and tosyloxylation via a five-membered exo-palladacycle. PG=protecting group, Ts=4-toluenesulfonyl.

Palladium-catalyzed cross-coupling of n -sulfonylaziridines with boronic acids

A mild palladium-catalyzed cross-coupling of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is presented. The reaction is highly regioselective and compatible with diverse functionality. A catalytic amount of base, a sterically demanding triarylphosphine ligand, and a phenol additive are critical to the success of the reaction. Coupling of a deuterium-labeled substrate established that ring opening of the aziridine occurs with inversion of stereochemistry.

Gold versus silver-catalyzed intermolecular hydroaminations of alkenes and dienes

Comparative studies about the hydroamination of unactivated alkenes and dienes catalyzed by either cationic gold(I) triphenyl phosphite complexes or silver salts were performed using sulfonamides, anilines and carbamates as nucleophiles. Gold-catalyzed reactions generally, need lower loadings than those carried out with silver salts. Simple alkenes react only with sulfonamides and weak aromatic amines such as p-nitroaniline, whereas for conjugated dienes carbamates can also be used. Carbon-carbon double bond isomerization is observed only with gold similarly to when triflic acid was used, affording mixtures of regioisomeric products in the same cases. Silver-catalyzed hydroaminations failed with terminal alkenes, except with styrenes. Conjugate dienes can be hydroaminated either at 85 °C in toluene or at room temperature in dichloromethane. Non-conjugated 1,4- and 1,5-dienes suffer double hydroamination leading to saturated N-tosylated heterocyclic amines The catalytic cycle for the silver(I)-catalyzed hydroamination process has been computationally analyzed, resembling gold(I)-catalyzed processes, although with some significant differences. Copyright

Inter- and intramolecular hydroamination of unactivated alkenes catalysed by a combination of copper and silver salts: The unveiling of a Bronstedt acid catalysis

The combined use of a copper halide, a silver salt and a phosphane ligand was applied for the catalysis of inter- and intramolecular hydroamination of alkenes. The reactions of unactivated olefins with nitrogen substrates were investigated. Mechanistic investigations demonstrated that the catalytic system generated a Bronsted acid which appeared to be the prominent catalytic species. Copyright

Recyclable gallium as catalyst precursor for a convenient and solvent-free method for the intermolecular addition of sulfonamides to alkenes

Gallium(III) iodide, which is conveniently formed in situ from gallium and iodine, is a competent catalyst for the inter- and intramolecular addition of p-toluenesulfonamides to alkenes. After each reaction, the metallic gallium can easily be recycled and used for subsequent transformations. Georg Thieme Verlag Stuttgart.

Arylbutyltellurides as precursors of dilithium arylthienylcyanocuprates in a straightforward approach to phenethylamine derivatives

The ring opening reaction of N-tosyl aziridines with dilithium arylthienylcyanocuprates generated from arylbutyltellurides produced phenethylamine derivatives in good to excellent yields.

InBr3 Catalyzed intermolecular hydroamination of unactivated alkenes

InBr3 has been demonstrated to be a simple catalyst for the intermolecular hydroamination of unactivated alkenes to produce tosyl- and mesyl-protected amines in moderate to good yields.

Regioselectivity in Nucleophilic Ring Opening of 2-Methylaziridines. Lag of Bond Making as Model for the Abnormal Opening

The regioselectivity ratio RS=normal:abnormal opening of activated 2-methylaziridines 2 by nucleophiles is found to range from 0.10 to unmeasurable large (only normal opening=substitution at CH2 by strongly basic carbanions).RS is assumed to result from SN2 variants differing in the degree to which bond breaking is ahead of bond making including perhaps synchronous SN2.Bond breaking will be more ahead for the N-CMe bond.High nucleophilic power pushes bond making toward a synchronous process resulting in great RS.The decrease in RS with acyl activation relative to sulfonyl activation is in accord with a flattening of the nitrogen pyramid (planarization effect).The planarization effect is retained in acidic medium by O-protonation: RS 0.10-0.14 for methanolysis as compared to RS 0.43 for N-protonated sulfonylaziridine 2h.AM1 calculations support the planarization hypothesis. - No indication for SET with trityl anion was found.

Sulphonamidomercuriation of Olefins and Subsequent Reductive Demercuriation or Bromodemercuriation

The addition of toluene-p-sulphonamide to olefins in the presence of anhydrous mercury(II) nitrate and subsequent sodium borohydride reduction leads to the corresponding N-alkylsulphonamides.The sulphonamidomercuriation-demercuriation of 1,4- and 1,5-dienes yields saturated nitrogen-containing heterocycles.A possible mechanism for the stereoselective synthesis of cis-2,5-dimethyl-N-tosylpyrrolidine is proposed.The treatment of the intermediate organomercurials, isolated as the sodium salts of their bromomercurio derivatives, with bromine gives the corresponding 2-bromoalkylsulphonamides through a regiospecific bromodemercuriation process.