5485-71-2

Upstream product

• 100-42-5 styrene 
• 67-66-3 chloroform 
• 21849-40-1 dibromamine-T 
• 13150-75-9 S,S-dimethyl-N-p-tolylsulfonylsulfimine 
• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 70-55-3 toluene-4-sulfonamide 
• 41085-71-6 bromamine T 
• 127-65-1 chloroamine-T 
• 109-99-9 tetrahydrofuran 
• 75-05-8 acetonitrile 
• 92755-81-2 N-bromo-p-toluenesulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 

Downstream Products

• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 81120-69-6 N-tosyl-2-methyl-4-phenyl-Δ²-pyrroline 
• 81097-27-0 N-tosyl-2,3-dimethyl-4-phenyl-Δ²-pyrroline 
• 81097-31-6 N-tosyl-2-phenyl-5-hexenylamine 
• 345301-56-6 N-tosyl-2-phenyl-3-methyl-4-pentenylamine 
• 70197-11-4 4-methyl-N-(2-phenylpent-4-en-1-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Bromosulfonamidation of alkenes using S,S-dimethyl-N-(p-toluenesulfonyl)sulfilimine

A new method for the bromosulfonamidation of olefins using a combination of S,S-dimethyl-N-(p-toluenesulfonyl)sulfilimine and N-bromosuccinimide is disclosed herein.

(+)-tartaric acid-catalyzed high regio- and stereoselective aminobromination of olefins

(+)-Tartaric acid-catalyzed aminobromination of α,β-unsaturated ketones, α,β-unsaturated esters and simple olefins utilizing TsNH2/NBS as the nitrogen/halogen sources at room temperature without protection of inert gases achieved good yields (u

Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH4)2S2O8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.

A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: Catalytic olefin aziridination reactions

A bromo-capped metal-metal bonded diruthenium(i,i) complex Ru2(CO)4(PIN)2Br2 (1) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with N-bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiometric reactions with 1 and NBS. An analysis of the dibrominated products suggests the formation of cyclic bromonium intermediates indicating in situ Br2 generation. Complex 2, an iodide analogue of 1, is also synthesized. The reaction of 2 with N-iodosuccinimide releases I2, which is confirmed by the starch-iodine test. The catalytic utility of 1 is examined for the bromination of phenol. Catalyst 1, in combination with NBS and base, exhibits regioselectivity towards monobrominated products. Furthermore, efficient olefin aziridination is demonstrated utilizing catalyst 1 in the presence of NBS, K2CO3 and TsNH2.

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 Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr2

N,N-Dibromo-p-toluene sulfonamide (TsNBr2) has been found to be an effective reagent for various aminofunctionalization reactions. This reagent behaves both as an electrophilic bromine source as well as amine to react with olefins under different conditions to yield aminoether, imidazoline, diamine and amino bromine. The reaction proceeds rapidly under mild conditions with high regioselectivity. Olefins react with TsNBr2 in moist THF to form δ-amino ether at room temperature. Treatment of TsNBr2 with olefin in MeCN at room temperature produced imidazoline in high yield. Further modification of the reaction condition resulted in the development of a one-step procedure for the synthesis of N-acetyl,N′-tosyl diamine derivatives directly from olefin. When the olefin was treated with 2.4 mol equiv of TsNBr2 in the presence of K2CO3, N,N′-ditosyl diamine derivative was obtained in moderate yield. Instantaneous formation of aminobromine was observed when an olefin was treated with the reagent in dry CH2Cl2 at room temperature.

Catalyst-free and metal-free electrophilic bromoamidation of unactivated olefins using the N-bromosuccinimide/sulfonamide Protocol

An efficient, catalyst-free, and metal-free bromoamidation of unactivated olefins has been developed. 4-(Trifluoromethyl)benzenesulfonamide and N-bromosuccinimide were used as the nitrogen and halogen sources, respectively. The methodology is applicable to both cyclic and aliphatic olefins.

Regioselective (Diacetoxyiodo)benzene-promoted halocyclization of unfunctionalized olefins

A metal-free method for intramolecular halocyclization of unfunctionalized olefins was detailed. (Diacetoxyiodo)benzene (PIDA) was very effective for haloamidation, haloetherification, and halolactonization of unfunctionalized olefins. In the presence of

Regioselective Ring-Opening Nucleophilic Addition of Aziridines through Photoredox Catalyst

A mild and efficient procedure was developed for the regioselective ring-opening nucleophilic addition reactions of aziridines via visible light photoredox catalysis, that provides a practical synthetic access to 1,2-bifunctional compounds. Furthermore, the regioselective synthesis of non-racemic amino ethers from chiral aziridine could also be achieved under mild conditions. Finally, a possible reaction mechanism was proposed and further supported by control experiments.

Hydrated nickel (II) halides mediated ring opening reaction with N-tosylaziridines

An efficient and water tolerant method for the synthesis of β-haloamines is described utilizing hydrated nickel (II) halides (NiX 2·nH2O X = Cl, Br, I) and aziridines as starting materials. N-Tosylaziridines reacted with NiCl2/