83706-39-2

Upstream product

• 108-86-1 bromobenzene 
• 4381-25-3 S-methyl-S-phenylsulfoximine 
• 17763-67-6 Phenyl triflate 
• 591-50-4 iodobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 2996-92-1 phenyl trimethylsiloxane 
• 94-36-0 dibenzoyl peroxide 
• 658-33-3 phenylsulfurimidoyl difluoride 
• 62-53-3 aniline 
• 42300-67-4 (±)-N-phenylmethanesulfinamide 
• 59-88-1 phenylhydrazine hydrochloride 
• 100-63-0 phenylhydrazine 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 100-58-3 phenylmagnesium bromide 

Relevant academic research and scientific papers

Catalytic coupling of aryl sulfonates with sp2-hybridized nitrogen nucleophiles: Palladium- and nickel-catalyzed synthesis of N-aryl sulfoximines

Several sulfoximines have been arylated in good to high yield by palladium catalysis using aryl nonaflates and aryl triflates. Moreover, the successful synthesis of N-aryl sulfoximines from aryl tosylates is described using a Ni(COD)2/BINAP catalyst.

Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis

A novel strategy for the N-arylation of NH-sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a NiII species is crucial to promote the reductive elimination of a C?N bond from the resulting NiIII species at room temperature.

Copper catalyzed N-arylation of sulfoximines with aryldiazonium salts in the presence of DABCO under mild conditions

N-Arylation of sulfoximines with aryldiazonium tetrafluoroborates is demonstrated in the presence of copper chloride and DABCO. A wide range of aryl and alkyl sufoximines are participated in the coupling reaction with different aryldiazonim salts bearing electron donating and withdrawing groups and provided the desired products in 67–88percent yields. The reaction proceeds through a radical mechanism.

Copper-Catalyzed N -Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions

N -Arylation of sulfoximines with different arylboronic acids, including sterically hindered boronic acids, is achieved using copper(I) iodide and 4-DMAP at room temperature. Moreover, N -arylation of biologically relevant l -methionine sulfoximine is demonstrated for the first time. All these reactions provided the desired products in excellent yields within a short span of time. The optimized reaction conditions are well suited to the task of N -vinylation of sulfoximine with trans -2-phenylvinylboronic acid.

Sulfonyl imide or sulfonamide of the denitrification arylation method and product and application

A sulfonyl imide or sulfonamide of the denitrification arylation method and product and application, sulfonimide or sulfonamide of the denitrification arylation method, comprises the following steps: to arylhydrazine and sulfonyl imide or sulfonamide as raw material, the catalyst palladium salt, alkali, solvent and oxidizing agent in the presence of, prepared N - aryl sulfonyl imide or N - aryl sulfonamides. The sulfonimide or sulfonamide of the denitrification arylation method, by adopting the arylhydrazine and sulfonimide or sulfonamide as raw materials used to prepare N - aryl sulfonyl imide or N - aryl sulfonamides, arylhydrazine because of having low cost, high reactivity and easy accessibility and the like, can make the sulfonyl imide or a sulfonamide for the arylation of the method cost is relatively low. The arylhydrazine as aryl group donor, the reaction by-product is N2 And H2 O, so it has the characteristics of green and environmental protection.

Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines

A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by arylhydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance (up to 36 examples). The protocol was proposed to take place through the free radical pathway based on the results of control reactions and EPR analysis.

SuFEx Chemistry of Thionyl Tetrafluoride (SOF4) with Organolithium Nucleophiles: Synthesis of Sulfonimidoyl Fluorides, Sulfoximines, Sulfonimidamides, and Sulfonimidates

Thionyl tetrafluoride (SOF4) is a valuable connective gas for sulfur fluoride exchange (SuFEx) click chemistry that enables multidimensional linkages to be created via sulfur–oxygen and sulfur–nitrogen bonds. Herein, we expand the available SuFEx chemistry of SOF4 to include organolithium nucleophiles, and demonstrate, for the first time, the controlled projection of sulfur–carbon links at the sulfur center of SOF4-derived iminosulfur oxydifluorides (R1?N=SOF2). This method provides rapid and modular access to sulfonimidoyl fluorides (R1?N=SOFR2), another array of versatile SuFEx connectors with readily tunable reactivity of the S?F handle. Divergent connections derived from these valuable sulfonimidoyl fluoride units are also demonstrated, including the synthesis of sulfoximines, sulfonimidamides, and sulfonimidates.

Sulfonimidates: Useful Synthetic Intermediates for Sulfoximine Synthesis via C-S Bond Formation

Medicinally relevant sulfoximines are accessed from C-S coupling of sulfonimidates and commercially available organomagnesium reagents. Sulfonimidates are conveniently synthesized by oxidative alkoxylation of readily available sulfinamides. This constitutes a general C-S coupling approach for the synthesis of sulfoximines.

Sulfoximines from a Medicinal Chemist's Perspective: Physicochemical and in vitro Parameters Relevant for Drug Discovery

Sulfoximines, sulfondiimides and sulfonimidamides are fascinating but not yet fully explored variants of the common sulfone or sulfonamide motif. In this study, we report the physicochemical and in vitro properties of sulfoximines and compare them with related analogs and isosteres. Furthermore, we present a matched molecular pair analysis of compounds from drug discovery projects within Boehringer Ingelheim. We demonstrate that the sulfoximine moiety is a chemically stable, comparatively polar and weakly basic functional group, often leading to favorable aqueous solubility, permeability and metabolic stability. Moreover, their additional vectors at nitrogen enable simple chemical modifications and thus facilitate exploration and fine-tuning of the molecular properties. We conclude that sulfoximines and their congeners do not exhibit any intrinsic flaw but significantly enrich the toolbox of medicinal chemists.

Radical N-arylation/alkylation of sulfoximines

A novel copper-catalyzed N-arylation/alkylation of sulfoximines with acyl peroxides as aryl/alkyl source was developed. This approach undergoes a radical pathway, representing an alternative complement to construct N-arylated/alkylated sulfoximines.