1125576-35-3

Upstream product

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

Downstream Products

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

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

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.

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.

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.