383-41-5

Upstream product

• 459-47-2 1-ethyl-4-fluorobenzene 
• 942066-10-6 N-[1-(4-fluoro-phenyl)-ethylidene]-4-methyl-benzenesulfonamide 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 13061-96-6 dihydroxy-methyl-borane 
• 193675-43-3 N-(4-fluorobenzylidene)-4-methylbenzenesulfonamide 
• 403-40-7 1-(4-fluorophenyl)ethylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 70-55-3 toluene-4-sulfonamide 
• 905272-80-2 N-p-toluenesulfonyl-4-fluoroacetophenone amine 
• 6873-55-8 p-tolylsulfinyl amide 
• 405-99-2 para-fluorostyrene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 

Downstream Products

• 1333226-32-6 C₂₂H₂₂FNO₄S₂ 

Relevant academic research and scientific papers

An Antimony(V) Dication as a Z-Type Ligand: Turning on Styrene Activation at Gold

With the intent to demonstrate that the charge of Z-type ligands can be used to modulate the electrophilic character and catalytic properties of coordinated transition metals, we are now targeting complexes bearing polycationic antimony-based Z-type ligands. Toward this end, the dangling phosphine arm of ((o-(Ph2P)C6H4)3)SbCl2AuCl (1) was oxidized with hydrogen peroxide to afford [((o-(Ph2P)C6H4)2(o-Ph2PO)C6H4)SbAuCl2]+ ([2 a]+) which was readily converted into the dicationic complex [((o-(Ph2P)C6H4)2(o-Ph2PO)C6H4)SbAuCl]2+ ([3]2+) by treatment with 2 equiv AgNTf2. Both experimental and computational results show that [3]2+ possess a strong Au→Sb interaction reinforced by the dicationic character of the antimony center. The gold-bound chloride anion of [3]2+ is rather inert and necessitates the addition of excess AgNTf2 to undergo activation. The activated complex, referred to as [4]2+ [((o-(Ph2P)C6H4)2(o-Ph2PO)C6H4)SbAuNTf2]2+ readily catalyzes both the polymerization and the hydroamination of styrene. This atypical reactivity underscores the strong σ-accepting properties of the dicationic antimony ligand and its activating impact on the gold center.

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.

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.

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.

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.

Redox Self-Adaptation of a Nitrene Transfer Catalyst to the Substrate Needs

The development of iron catalysts for carbon–heteroatom bond formation, which has attracted strong interest in the context of green chemistry and nitrene transfer, has emerged as the most promising way to versatile amine synthetic processes. A diiron system was previously developed that proved efficient in catalytic sulfimidations and aziridinations thanks to an FeIIIFeIV active species. To deal with more demanding benzylic and aliphatic substrates, the catalyst was found to activate itself to a FeIIIFeIVL. active species able to catalyze aliphatic amination. Extensive DFT calculations show that this activation event drastically enhances the electron affinity of the active species to match the substrates requirements. Overall this process consists in a redox self-adaptation of the catalyst to the substrate needs.

FeCl3-catalyzed addition of nitrogen and 1,3-dicarbonyl nucleophiles to olefins

A direct intermolecular addition of nitrogen and 1,3-dicarbonyl nucleophiles to stabilized double bonds (styrenes, 1,3-dienes, enol-ethers, sugars.) in the presence of green and inexpensive FeCl3 catalyst is described.

Cross-coupling of grignard reagents with sulfonyl-activated sp3 carbon-nitrogen bonds

Sulfonyl-activated sp3 carbon-nitrogen bonds have been found to be cleaved by Grignard reagents in the presence of 5 mol% of copper(I) iodide (CuI). Significantly, a broad range of sulfonyl-activated benzylic, allylic, and propargylic amines smoothly undergo the cross-coupling reaction with Grignard reagents to afford structurally diverse coupling products in good to excellent yields and with high chemo-, regio-, and stereoselectivity. Moreover, an S N2 mechanism has been demonstrated to be involved in the cross-coupling reaction that allows the asymmetric synthesis of chiral hydrocarbons from optically active α-branched amine derivatives. Copyright

Highly enantioselective Pd-catalyzed asymmetric hydrogenation of activated imines

(Chemical Equation Presented) Pd/bisphosphines complexes are highly effective catalysts for asymmetric hydrogenation of activated imines in trifluoroethanol. The asymmetric hydrogenation of N-diphenylphosphinyl ketimines 3 with Pd(CF3CO2)/(S)-SegPhos indicated 87-99% ee, and N-tosylimines 5 could gave 88-97% ee with Pd-(CF3CO 2)/(S)-SynPhos as a catalyst. Cyclic N-sulfonylimines 7 and 11 were hydrogenated to afford the useful chiral sultam derivatives in 79-93% ee, which are important organic synthetic intermediates and structural units of agricultural and pharmaceutical agents.

Intermodular FeCl3-catalyzed hydroamination of styrenes

Hydroamination reactions of vinylarenes with nonnucleophilic nitrogen derivatives (p-toluenesulfonamide, p-nitroaniline, p-nitrobenzamide, ...) catalyzed by FeCl3 are described. Interestingly, these reactions are catalyzed by an environmentally