56157-97-2

Upstream product

• 108-86-1 bromobenzene 
• 1520-31-6 dimethylsulfoximine 
• 591-50-4 iodobenzene 
• 75-16-1 methylmagnesium bromide 
• 98-80-6 phenylboronic acid 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 2996-92-1 phenyl trimethylsiloxane 
• 66003-76-7 Diphenyliodonium triflate 

Downstream Products

• 6798-41-0 2-N,N-dimethylamino-3H-azepine 
• 17082-12-1 trans-azobenzene 

Relevant academic research and scientific papers

Palladium-catalyzed carbon-nitrogen bond formation: A novel, catalytic approach towards N-arylated sulfoximines

The coupling of sulfoximines 1 with various aryl bromides of different substitution pattern in the presence of a catalytic amount of Pd(OAc)2 and a chelating bisphosphine affords N-arylated products 3 with yields of up to 96%.

Photoredox mediated C[sbnd]N cross coupling of sulfoximines with aryl iodides

A new photoredox-catalyzed C[sbnd]N coupling reaction of sulfoximines with aryl halides has been developed for a general N-arylation of sulfoximines. The reactions proceed in the presence of visible light with high levels of chemoselectivity and a wide ra

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.

Metal-Free Approach for the Synthesis of N-Aryl Sulfoximines via Aryne Intermediate

A metal-free and operationally simple N-arylation of NH-sulfoximines with aryne precursors is reported. Transition metal-free reaction conditions and shorter reaction times are the highlights of the present method. The mild optimized condition was also found to be suitable with enantiopure substrates.

Mild copper-TBAF-catalyzed N-arylation of sulfoximines with aryl siloxanes

An efficient copper-TBAF-catalyzed C-N bond formation of sulfoximines with arylsiloxanes in dichloromethane at room temperature, affording the desired N-aryl sulfoximines in good to excellent yields under an oxygen atmosphere, is reported. This method complements the existing synthetic approaches due to some advantageous properties of arylsiloxanes such as availability, low toxicity, ease of handling, high stability, and environmental benignity under mild reaction conditions, thus opening a new approach to practical C-N bond formation.

Copper-catalyzed ultrasound-expedited N-arylation of sulfoximines using diaryliodonium salts

An ultrasound-accelerated route for an expeditious N-arylation of NH-sulfoximines is described that involves the use of diaryliodonium salts in aqueous polyethylene glycol-400 and copper(I) bromide as catalyst at room temperature. The high yields of the p

Iron-catalyzed C-N cross-coupling of sulfoximines with aryl iodides

An inexpensive and experimentally simple, iron-catalyzed N-arylation reaction of NH-sulfoximines with aryl iodides is reported. This complementary method to the known palladium- and copper-catalyzed ones features the use of a combination of environmentall

Palladium-catalyzed N-arylation of sulfoximines with aryl bromides and aryl iodides

Various N-arylated sulfoximines have been synthesized in high yield by a direct approach which is based on a palladium-catalyzed cross-coupling strategy. Aryl bromides of variable substitution pattern were found to be the most effective coupling partners,