25566-59-0

Upstream product

• 60-12-8 2-phenylethanol 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 100-42-5 styrene 
• 624-31-7 4-tolyl iodide 
• 589-08-2 N-Methyl-N-phenethylamine 
• 5450-75-9 4-methyl-N-(2-phenylethyl)benzenesulfonamide 
• 74-88-4 methyl iodide 
• 1093198-49-2 phenethyl 2-(phenylethynyl)benzoate 

Downstream Products

• 536-57-2 p-toluene sulfinic acid 
• 1858-86-2 Ethyl p-toluenesulfinate 
• 672-78-6 methyl p-toluene sulfinate 
• 589-08-2 N-Methyl-N-phenethylamine 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 

Relevant academic research and scientific papers

Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications

Herein we report a catalyst- and metal-free visible-light-mediated protocol enabling the iodoamination of miscellaneous olefins. This protocol is characterized by high yields under environmentally benign reaction conditions utilizing commercially available substrates and a green and biodegradable solvent. Furthermore, the protocol allows for late-stage functionalization of bioactive molecules and can be scaled to gram quantities of product, which offers manifold possibilities for further transformations, including morpholine, piperidine, pyrrolidine, and aziridine synthesis.

Design and Applications of a SO2 Surrogate in Palladium-Catalyzed Direct Aminosulfonylation between Aryl Iodides and Amines

A new SO2 surrogate is reported that is cheap, bench-stable, and can be accessed in just two steps from bulk chemicals. Essentially complete SO2 release is achieved in 5 minutes. Eight established sulfonylation reactions proceeded smoothly by ex situ formation of SO2 by utilizing a two-chamber system in combination with the SO2 surrogate. Furthermore, we report the first direct aminosulfonylation between aryl iodides and amines. Broad functional group tolerance is demonstrated, and the method is applicable to pharmaceutically relevant substrates, including heterocyclic substrates.

Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent

ortho-Alkynylbenzoic acid alkyl esters behave as alkylating agents in combination with gold catalysts. The reaction with alcohols occurs smoothly in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce the corresponding ether products in high yields. The protocol is also useful for Friedel-Crafts alkylation and N-alkylation of sulfonamides. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of nucleophiles, such as alcohols, aromatic compounds, and sulfonamides.

Mitsunobu type C-N bond formation with 4,7-dimethyl-3,5,7-hexahydro-1,2,4,7-tetrazocin-3,8-dione(DHTD), a new cyclic azodicarboxamide

The combination of 4,7-dimethyl-3,5,7-hexahydro-1,2,4,7-tetrazocin-3,8-dione (DHTD) and tributylphosphine (TBP) was found to mediate successfully C-N bond formation between N-methyltosylamide, a typical N-nucleophile, and several alcohols of different structural types. The unique feature of this combination is that it activates the reaction of sec-alcohols at room temperature.

MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES

N-Methyl p-toluenesulfonamide and N-BOC p-toluenesulfonamide can be directly coupled with primary or secundary alcohols under Mitsunobu conditions to afford various sulfonamide-protected amines.