1125576-35-3

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 941-55-9 4-toluenesulfonyl azide 
• 1515-95-3 p-ethylanisole 
• 842120-96-1 N-[1-(4-methoxyphenyl)-ethylidene]-4-methyl-benzenesulfonamide 
• 127-65-1 chloroamine-T 
• 6298-96-0 1(R)-(4-methoxyphenyl)-ethylamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 97637-73-5 N-[1-(4-methoxyphenyl)ethyl]-p-toluenesulfonamide 
• 107270-96-2 1-(1-Benzenesulfonyl-ethyl)-4-methoxy-benzene 
• 865541-03-3 (R)-3-(4-methoxyphenyl)-1-phenylbutan-1-one 
• 87258-61-5 (S)-(+)-3-p-methoxyphenyl-1-phenylbutan-1-one 
• 129919-76-2 3-(4-methoxyphenyl)-1,3-diphenyl-1-propanone 

Relevant academic research and scientific papers

Nickel-Catalyzed Asymmetric Transfer Hydrogenation and α-Selective Deuteration of N-Sulfonyl Imines with Alcohols: Access to α-Deuterated Chiral Amines

A nickel-catalyzed enantioselective transfer hydrogenation and deuteration of N-sulfonyl imines was developed. Excellent α-selectivity and high deuterium content were achieved by using inexpensive 2-propanol-d8 as a deuterium source. As a highlight, no deuteration of β-C-H and the remote C-H of N-sulfonyl amines occurred, which is hard to achieve using other imines or by hydrogen isotope exchange with D2O. Mechanism studies indicated a stepwise pathway through the [Ni-D] intermediate.

Asymmetric Stepwise Reductive Amination of Sulfonamides, Sulfamates, and a Phosphinamide by Nickel Catalysis

Asymmetric reductive amination of poorly nucleophilic sulfonamides was realized in the presence of nickel catalysts and titanium alkoxide. A wide range of ketones, including enolizable ketones and some biaryl ones, were converted into sulfonamides in excellent enantiomeric excess. The cyclization of sulfamates and intermolecular reductive amination of a diarylphosphinamide were also successful. Formic acid was used as a safe and economic surrogate of high-pressure hydrogen gas.

Enantioselective, intermolecular benzylic C-H amination catalysed by an engineered iron-haem enzyme

C-H bonds are ubiquitous structural units of organic molecules. Although these bonds are generally considered to be chemically inert, the recent emergence of methods for C-H functionalization promises to transform the way synthetic chemistry is performed. The intermolecular amination of C-H bonds represents a particularly desirable and challenging transformation for which no efficient, highly selective, and renewable catalysts exist. Here we report the directed evolution of an iron-containing enzymatic catalyst - based on a cytochrome P450 monooxygenase - for the highly enantioselective intermolecular amination of benzylic C-H bonds. The biocatalyst is capable of up to 1,300 turnovers, exhibits excellent enantioselectivities, and provides access to valuable benzylic amines. Iron complexes are generally poor catalysts for C-H amination: in this catalyst, the enzyme's protein framework confers activity on an otherwise unreactive iron-haem cofactor.

Efficient asymmetric transfer hydrogenation of N-sulfonylimines on water

An efficient and green approach for synthesis of optically active amines was developed via asymmetric transfer hydrogenation of N-sulfonyl ketimines catalyzed by the chiral and lipophilic rhodium-amido complex on water. Higher reactivity and enantioselect

Ligand-assisted, copper-catalyzed enantioselective benzylic amination

Several classes of ligands, including α-amino acids, diamines, diphosphines, bis-oxazolines, and diimines, support efficient copper-catalyzed amination of benzylic hydrocarbons by anhydrous chloramine-T. Catalysts derived from homochiral ligands, particularly chiral diimines, effect aminosulfonation with low to moderate enantioselectivity.

Catalytic coupling of N-benzylic sulfonamides with silylated nucleophiles at room temperature

In the presence of 2-10 mol% of Tf2NH, a range of N-benzylic sulfonamides smoothly react with allylic, propargylic, benzylic, or hydrido silanes at room temperature via sp3 carbon-nitrogen bond cleavage to afford structurally diverse products in moderate to excellent yields and with high chemo- and regioselectivity.

Selective benzylic and allylic alkylation of protic nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds

The acid-catalyzed benzylic and allylic alkylation of protic nucleophiles is fundamentally important for the formation of carbon-carbon and carbon-heteroatom bonds, and it is a formidable challenge for benzylic and allylic amine derivatives to be used as the alkylating agents. Herein we report a highly efficient benzylic and allylic alkylation of protic carbon and sulfur nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp3 carbon-nitrogen bonds at room temperature. In the presence of a catalytic amount of inexpensive ZnCl2-TMSCl (TMSCl: chlorotrimethylsilane), 1,3-diketones, β-keto esters, β-keto amides, malononitrile, aromatic compounds, thiols, and thioacetic acid can couple with a broad range of tosylactivated benzylic and allylic amines to give diversely functionalized products in good to excellent yields and with high regioselectivity. Furthermore, the cross-coupling reaction of 1,3-dicarbonyl compounds with benzylic propargylic amine derivatives has been successfully applied to the one-step synthesis of polysubstituted furans and benzofurans.