54755-72-5

Upstream product

• 50-00-0 formaldehyd 
• 22731-83-5 S,S-diphenylsulphoximine 
• 74-88-4 methyl iodide 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 13061-96-6 dihydroxy-methyl-borane 
• 75-91-2 tert.-butylhydroperoxide 
• 614-45-9 tert-Butyl peroxybenzoate 
• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 
• 110-05-4 di-tert-butyl peroxide 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 

Downstream Products

• 70355-70-3 N-acetyl-S,S-diphenylsulfoximine 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed C?H Alkynylation of N-Methylsulfoximines

A rhodium(III)-catalyzed direct C?H alkynylation of a wide range of N-methylsulfoximines with (bromoethynyl)triisopropylsilane has been developed. This protocol is compatible with both (S,S)-diaryl sulfoximines and (S,S)-alkyl aryl sulfoximines, and shows mild conditions, and good functional group tolerance. The synthetic utility of this method has been demonstrated by subsequent various transformations of the products.

N - methylation of the sulfoxide of imine derivative (by machine translation)

A simple, clean and high-effective synthetic method of a novel N-methylated sulfoximine derivative is provided in the invention. The invention relates to the fields of pesticides, organic chemical engineering and fine chemical engineering. The method essentially is an organic synthesis reaction that a methyl free radical, which is generated from peroxides, and a sulfoximine compound are subjected to free radical coupling to form new C-N bonds. The method includes the step of carrying out a reaction to obtain the N-methylated sulfoximine derivative in a common organic solvent under a heating condition from the raw materials including diphenyl sulfoximine and a methylating reagent (peroxides) under the catalysis by copper. The method is 2-20 h in reaction time under a heating and stirring condition. The molar ratio of the raw materials is that the diphenyl sulfoximine to the methylating reagent is 1:0.5-3.0. The raw materials are reacted under the heating condition and then reaction products are subjected to simple after treatments to obtain the N-methylated sulfoximine derivative at a yield being 36-87%. The invention develops a series of N-methylating methods based on a free radical process to prepare a series of N-methylated sulfoximine derivatives. The method is simple in operation and after treatments, and is simple and practical in synthesis of these compounds.

Copper promoted: N -alkylation of sulfoximines with alkylboronic acid under mild conditions

The copper meditated N-methylation of sulfoximines using methylboronic acid is reported. The reactions provide excellent yields in a short span of time under mild conditions. The optimized conditions were also found to be suitable for the N-alkylation of sulfoximine with different alkylboronic acids. In addition, N-methylation and cyclopropylation of the bioactive l-methionine sulfoximine derivative was demonstrated under standard reaction conditions.

Microwave-Assisted Cp*CoIII-Catalyzed C-H Activation/Double C-N Bond Formation Reactions to Thiadiazine 1-Oxides

A microwave-assisted, Cp*CoIII-catalyzed direct C-H activation/double C-N bond formation reaction of simple NH-sulfoximines with 1,4,2-dioxazol-5-ones to produce diverse thiadiazine-1-oxides is reported. The reaction tolerates a broad range of functional groups under external oxidant-free conditions and only releases CO2 and H2O as the sole byproducts. The preliminary mechanistic studies revealed an electrophilic metalation pathway is likely involved in the reaction.

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.

Iron-Catalyzed Acylative Dealkylation of N-Alkylsulfoximines

As a result of our recent investigations into the N-functionalization of sulfoximines, an iron-catalyzed dealkylative acylation of N-alkylsulfoximines has been developed. This process involves a Polonovski-type dealkylation of an N-alkylated sulfoximine to afford a reactive intermediate that is trapped in the presence of a suitable aldehyde or anhydride to afford N-acyl- and N-aroylsulfoximine derivatives in one pot. Subsequent cleavage of the acyl or aroyl group under acidic conditions generates a synthetically valuable NH-sulfoximine. The dealkylation of N-alkylsulfoximines has been developed utilizing TBHP as oxidant and a catalytic amount of iron chloride to furnish a range of N-acyl- and N-aroylsulfoximines. This method facilitates the use of N-alkyl protecting groups that provide very stable N-protected sulfoximine derivatives that can be readily modified at sites other than the nitrogen atom.

Copper-catalyzed N-methylation/ethylation of sulfoximines

A protocol for the copper-catalyzed N-methylation of sulfoximines with di-tert-butyl peroxide (DTBP) was developed. This protocol has good functional group tolerance leading to N-methylated sulfoximines in moderate to good yields. Besides, N-ethylation of sulfoximines was achieved in the presence of bis(1,1-dimethylpropyl)peroxide as the ethylating agent under a standard procedure.