4809-56-7

Upstream product

• 24865-83-6 4-methyl-N-(1-phenylethylidene)benzenesulfonamide 
• 38436-37-2 hexafluoroacetone O-tosyloxime 
• 618-36-0 rac-methylbenzylamine 
• 917-54-4 methyllithium 
• 51608-60-7 phenyl N-tosyl imine 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 75-24-1 trimethylaluminum 
• 100-41-4 ethylbenzene 
• 18522-92-4 sodium p-toluenesulfonamide 
• 55962-05-5 4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 41085-71-6 bromamine T 
• 98-86-2 acetophenone 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 618-36-0 rac-methylbenzylamine 
• 5186-08-3 3-(1-phenyl-ethyl)-pentane-2,4-dione 
• 116140-58-0 1,3-diphenyl-2-(1-phenyl-ethyl)-propane-1,3-dione 
• 5870-49-5 1-phenyl-2-(1-phenylethyl)-1,3-butanedione 
• 1414850-53-5 4-methyl-N-(1-phenylethyl)-N-(phenylethynyl)benzenesulfonamide 
• 24865-83-6 4-methyl-N-(1-phenylethylidene)benzenesulfonamide 
• 72984-27-1 4-Methyl-N-((R)-1-phenyl-ethyl)-benzenesulfonamide 
• 51310-25-9 1-methyl-2,3-diphenylindene 
• 612-00-0 1,1'-ethylidenebis-benzene 
• 87010-94-4 C₁₅H₁₈N₂O₂S 

Relevant academic research and scientific papers

Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: Carbonic anhydrase inhibitory activity and: In silico study

The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF3) adsorbed on molecular sieves (4 ?) as a solid support catalyst for the preparation of sulfon

Decarboxylative cross-nucleophile coupling via ligand-to-metal charge transfer photoexcitation of Cu(ii) carboxylates

Reactions that enable carbon–nitrogen, carbon–oxygen and carbon–carbon bond formation lie at the heart of synthetic chemistry. However, substrate prefunctionalization is often needed to effect such transformations without forcing reaction conditions. The development of direct coupling methods for abundant feedstock chemicals is therefore highly desirable for the rapid construction of complex molecular scaffolds. Here we report a copper-mediated, net-oxidative decarboxylative coupling of carboxylic acids with diverse nucleophiles under visible-light irradiation. Preliminary mechanistic studies suggest that the relevant chromophore in this reaction is a Cu(ii) carboxylate species assembled in situ. We propose that visible-light excitation to a ligand-to-metal charge transfer (LMCT) state results in a radical decarboxylation process that initiates the oxidative cross-coupling. The reaction is applicable to a wide variety of coupling partners, including complex drug molecules, suggesting that this strategy for cross-nucleophile coupling would facilitate rapid compound library synthesis for the discovery of new pharmaceutical agents. [Figure not available: see fulltext.].

Site-Selective Electrochemical Benzylic C?H Amination

C?H/N-H cross-coupling is an ideal strategy to synthesize various amines but remains challenging owing to the requirement for sacrificial chemical oxidants and the difficulty in controlling the regio- and chemo-selectivity. Herein we report a site-selective electrochemical amination reaction that can convert benzylic C?H bonds into C-N linkages via H2 evolution without need for external oxidants or metal catalysts. The synthetic strategy involves anodic cleavage of benzylic C?H to form a carbocation intermediate, which is then trapped with an amine nucleophile leading to C?N bond formation. Key to the success is to include HFIP as a co-solvent to modulate the oxidation potentials of the alkylbenzene substrate and the aminated product to avoid overoxidation of the latter.

Copper-boryl mediated transfer hydrogenation of N-sulfonyl imines using methanol as the hydrogen donor

B2Pin2-assisted copper-catalyzed transfer hydrogenation of aromatic sulfonylimines has been achieved, delivering a variety of aryl/heteroaryl sulfonamides in good to excellent yields under mild reaction conditions and with methanol a

Direct Synthesis of α-Amino Nitriles from Sulfonamides via Base-Mediated C-H Cyanation

Herein, we disclose a transition-metal-free reaction system that enables α-cyanation of sulfonamides through C-H bond cleavage for the preparation of α-amino nitriles, including difficult-to-access all-alkyl α-tertiary scaffolds. More than 50 substrate examples prove a wide functional group tolerance. Additionally, its synthetic practicality is highlighted by gram-scalability and the late-stage modification of natural compounds. Mechanistic experiments suggest that this process involves in situ formation of an imine intermediate via base-promoted elimination of HF.

Organophotoredox-Catalyzed Decarboxylative N-Alkylation of Sulfonamides

We developed an organophotoredox-catalyzed reaction for N-alkylation of sulfonamides with aliphatic carboxylic acid-derived redox active esters as alkylating reagents. Under mild and transition metal-free conditions, a series of functionalized N-alkylated sulfonamides were prepared. This protocol also enabled the functionalization of pharmaceutical drugs bearing a sulfonamide or carboxylic acid moiety. This radical-mediated process allowed the assembly of three components including sulfonamides, redox active esters, and alkenes to yield complex sulfonamides in a one-pot manner.

A new generation of terminal copper nitrenes and their application in aromatic C-H amination reactions

Copper nitrene complexes are highly reactive species and are known as intermediates in the copper catalyzed C-H amination. In this study, three novel copper tosyl nitrene complexes were synthesized at low temperatures, stabilized with heteroscorpionate ligands of the bis(pyrazolyl)methane family. The copper nitrenes were obtained by the reaction of a copper(i) acetonitrile complex with SPhINTs in dichloromethane. We show that the ligand design has a major influence on the catalytic activity and the thermal stability of the copper nitrene complex. Not only the choice of the third N donor, but also the substituent in the 5-position of the pyrazolyl moiety, have an impact on the stability. Furthermore, the novel copper nitrene complexes were used for catalytic aziridination of styrenes and C-H amination reactions of aromatic and aliphatic substrates under mild reaction conditions. Even challenging substrates like benzene and cyclohexane were aminated with good yields. The copper nitrene complexes were characterized using UV/Vis spectroscopy, low temperature Evans NMR spectroscopy, density functional theory, domain-based local pair natural orbital coupled cluster calculations (DLPNO-CCSD(T)) and cryo-UHR mass spectrometry.

Chiral bis(pyrazolyl)methane copper(I) complexes and their application in nitrene transfer reactions

In this study, chiral bis(pyrazolyl)methane copper(I) acetonitrile complexes were applied to generate two novel terminal copper tosyl nitrene complexes with the nitrene generating agent SPhINTs in dichloromethane at low temperatures. The syntheses of the chiral bis(pyrazolyl)methane ligands are based on pulegone and camphor, members of the natural chiral pool. The chiral copper(I) acetonitrile complexes were applied as catalysts in the copper nitrene mediated aziridination reaction of different styrene derivatives and the C-H amination of various substrates. The reactions afforded good yields, but low enantiomeric excess under mild conditions. The nitrene species have been characterized with UV/Vis and EPR spectroscopy and the products of the decay by ESI mass spectrometry.

Development of a CuCl/phosphine system to catalyze phenylation and methylation of N-tosyl aldimines with phenylboronic andmethylboronic acids

The addition of phenylboronic and methylboronic acids to activated aromatic aldimines was demonstrated in the presence of copper(I)-phosphine complexes. The desired products were obtained using copper chloride/phosphine, and potassium fluoride in under toluene reflux, in moderate-to-good yield and a suitable reaction time.

Halogen-Bond-Induced Consecutive Csp3-H Aminations via Hydrogen Atom Transfer Relay Strategy

The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.