31280-33-8

Upstream product

• 67-68-5 dimethyl sulfoxide 
• 138815-29-9 N-Benzoyl-2-phenyl-4,5-dimethyl-1,2,3-triazol-1-imine 
• 1520-31-6 dimethylsulfoximine 
• 611-70-1 phenyl isopropyl ketone 
• 100-52-7 benzaldehyde 
• 611-73-4 Benzoylformic acid 
• 108-88-3 toluene 
• 495-18-1 Benzohydroxamic acid 
• 75-18-3 dimethylsulfide 
• 19226-36-9 3-phenyl-5H-1,4,2-dioxazol-5-one 
• 31400-24-5 Biacetyl Benzoylhydrazone Phenylhydrazone 
• 55590-53-9 biacetyl monobenzoyl hydrazone 
• 582-61-6 benzoyl azide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1377585-40-4 N-[2-hydroxybenzoyl]-S,S-dimethylsulfoximine 
• 1377585-27-7 N-[2-acetoxybenzoyl]-S,S-dimethylsulfoximine 

Relevant academic research and scientific papers

Visible light-induced C-C bond cleavage in a multicomponent reaction cascade allowing acylations of sulfoximines with ketones

Visible light induces C-C-bond cleavage reactions of ketones, which can be utilized forN-acylations of sulfoximines. No (photo)catalyst is required, and the reactions occur at ambient temperature in air. The substrate scope is broad for both ketones and sulfoximines. For convertingNH-sulfoximines, the presence of NBS is essential.

Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions

An efficient catalyst-free radical cross-coupling reaction between aromatic aldehydes and sulfoximines was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines in moderate to excellent yields (27 examples). This protocol proved to be rapid, easy to handle, and applicable to a broad scope of substrates.

Copper-catalyzed oxidative decarboxylative coupling of α-keto acids and sulfoximines

A copper-catalyzed oxidative decarboxylative coupling of α-keto acids with NH-sulfoximines has been developed. With CuBr as the catalyst and K2S2O8 as the oxidant, this reaction enables the formation of a C-N bond and gives N-aroylsulfoximine products in moderate to excellent yields. The reaction mechanism is likely to involve the generation of a reactive aroyl radical intermediate.

Copper-catalyzed preparation of N-aroylated sulfoximines from methylarenes

A copper-catalyzed methodology for the preparations of N-aroylated sulfoximines from methylarenes was herein demonstrated. The transformation proceeded with the assistance of external oxidant tert-butyl hydroperoxide, requiring for no additional solvents or ligands. The good compatibility and high efficiency of the newly developed protocol were well described by 21 examples and up to 91% yields. Moreover, the protocol was proved by the control reactions to proceed through a radical pathway.

Palladium-Catalyzed Direct α-Arylation of p -Methoxybenzyl-Protected S, S -Dimethylsulfoximine

Sulfoximines have recently gained considerable recognition as an important structural motif in the life sciences. This is especially true for (hetero)aryl-substituted S,S-dimethylsulfoximine derivatives, such as the marketed insecticide sulfoxaflor, as well as the clinical candidates PTEFb inhibitor BAY 1143572 and ATR inhibitor AZD 6738 for the treatment of cancer. Herein, the first palladium-catalyzed direct α-arylation of p-methoxybenzyl-protected S,S-dimethylsulfoximine using readily available (hetero)aryl bromides is reported. This new method provides a safe, short, and efficient approach to (hetero)aryl-substituted S,S-dimethylsulfoximine derivatives, an important class of bioactive compounds, demonstrated by application of this methodology to an improved synthesis of PTEFb inhibitor BAY 1143572.

Transition metal-free aroylation of NH-sulfoximines with methyl arenes

A novel protocol towards N-aroylated sulfoximines from NH-sulfoximines and methyl arenes was herein demonstrated. The reaction took place in the presence of elemental iodine, requiring no external organic solvents, transition metal-catalysts or ligands. The aroylated products were obtained from the oxidative transformation in moderate to excellent yields (up to 94% yield) with a broad substrate scope (35 examples) through a radical pathway.

Light-induced ruthenium-catalyzed nitrene transfer reactions: A photochemical approach towards N-Acyl sulfimides and sulfoximines

1,4,2-Dioxazol-5-ones are five-membered heterocycles known to decarboxylate under thermal or photochemical conditions, thus yielding N-acyl nitrenes. Described herein is a light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by decarboxylation of 1,4,2-dioxazol-5-ones at room temperature, thus providing direct access to N-acyl sulfimides and sulfoximines under mild reaction conditions. In addition, a one-pot sulfur imidation/oxidation sequence catalyzed by a single ruthenium complex is reported. Double duty: A one-pot sulfur imidation/oxidation sequence using a single ruthenium complex for both steps was developed (see scheme). Photochemical decarboxylations of 1,4,2-dioxazol-5-ones provide N-acyl nitrenes, which imidate sulfides at ambient temperature. The subsequent oxidation then occurs under mild phase-transfer catalysis conditions. In this manner, N-acyl sulfimides and sulfoximines can be obtained in high yields starting from sulfides.

Sulfoximines: A reusable directing group for chemo-and regioselective ortho C-H oxidation of arenes

Sulfoximines direct: A new protocol for the chemo-and regioselective ortho C-H acetoxylation of arenes in N-benzoylated sulfoximines is reported. The sulfoximine directing group is easily detached from the C-H oxidation product through acid-promoted hydrolysis, isolated, and reused (see scheme). The meta-substituted phenols are synthesized following this strategy and the stereointegrity of the sulfoximine is preserved in this transformation. C(sp3)-H acetoxylation of the methyl group is also demonstrated.

Electrochemical Imination of Sulfoxides Using N-Aminophthalimide

(Equation Presented) A novel electrochemical sulfoxide imination process is described. Our approach starts with a highly selective nitrene transfer from N-aminophthalimide to a variety of sulfoxides. This oxidative treatment is followed by reductive N-N bond cleavage under the controlled current conditions, which leads to a range of parent NH sulfoximines. In addition to solving the challenging problem of removing the N-phthalimido group, the overall process avoids the use of toxic oxidants and metal additives.

1,2,3-Triazol-1-imines. 1. The Synthesis and Lead Tetraacetate Oxidation of Biacetyl Benzoylhydrazone Arylhydrazones to the Novel 2-Aryl-N-benzoyl-4,5-dimethyl-1,2,3-triazol-1-imines

The synthesis and the Pb(OAc)4 oxidation of the mixed bishydrazones of biacetyl 7 was studied.The formation of the novel N-benzoyl-1,2,3-triazol-1-imines 9 from the oxidation of 7 provided support to the proposed in the past mechanism for the oxidation of bis-aroylhydrazones of α-dicarbonyl compounds 4.Thermolysis and photolysis of 9a in DMSO was carried out.The results suggested that benzoylnitrene was formed in the photochemical reaction, and therefore compounds such as 9 could serve as non-azide aroyl nitrene precursors.For 9a the results of the X-ray analysis were correlated with charge densities and bond orders gleaned by the MNDO method.Product 9d was alternatively synthesized by the addition of photochemically generated bezoylnitrene to the 1,2,3-triazole 21.