833459-47-5

Basic information

• Product Name: (2-bromophenyl)(imino)(methyl)-λ⁶-sulfanone
• Synonyms: (2-bromophenyl)(imino)(methyl)-λ⁶-sulfanone
• CAS NO: 833459-47-5
• Molecular Weight: 234.117
• Mol File: 833459-47-5.mol

Chemical Properties

• CAS DataBase Reference: (2-bromophenyl)(imino)(methyl)-λ⁶-sulfanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2-bromophenyl)(imino)(methyl)-λ⁶-sulfanone(833459-47-5)
• EPA Substance Registry System: (2-bromophenyl)(imino)(methyl)-λ⁶-sulfanone(833459-47-5)

Safety Data

• Hazardous Substances Data: 833459-47-5(Hazardous Substances Data)

Upstream product

• 126218-83-5 1-bromo-2-(methylsulfinyl)benzene 
• 19614-16-5 2-bromo-1-(methylsulfanyl)benzene 
• 6320-02-1 o-bromothiophenol 

Downstream Products

• 833459-71-5 (Z)-3-(4-tert-butylbenzylidene)-1-methyl-1-oxide-3H-1λ⁴-1,2-benzoisothiazole 
• 30194-74-2 (+/-)-1-methyl-1H,3H-1,2-benzisothiazol-3-one 1-oxide 

Relevant articles and documents

Rhodium(iii)-catalyzed cascade C-H functionalization/annulation of sulfoximines with iodonium ylides for the synthesis of cyclohexanone-1,2-benzothiazines

A highly efficient Rh(iii)-catalyzed cascade C-H activation/annulation of sulfoximines with iodonium ylides under metal-oxidant-free conditions has been reported. The fused cyclohexanone-1,2-benzothiazine scaffold is readily achieved with a one-pot proces

Electrochemical Oxidative Syntheses of NH-Sulfoximines, NH-Sulfonimidamides and Dibenzothiazines via Anodically Generated Hypervalent Iodine Intermediates

Herein, we report a general method for the synthesis of NH-sulfoximines and NH-sulfonimidamides through direct electrochemical oxidative catalysis involving an iodoarene(I)/iodoarene(III) redox couple. In addition, dibenzothiazines can be synthesized from [1,1′-biaryl]-2-sulfides under standard conditions. Notably, only a catalytic amount of iodoarene is required for the generation in situ of an active hypervalent iodine catalyst, which avoids the need for an excess of a hypervalent iodine reagent relative to conventional approaches. Moreover, this protocol features broad substrate scope and wide functional group tolerance, delivering the target compounds with good-to-excellent yields even for a scale of more than 10 g.

Preparation of S-2-halophenyl-2,1-benzothiazines

Derivatives of 2,1-benzothiazines are useful synthetic intermediates for a variety of applications. We became interested in developing a one-pot procedure to S-2-halophenyl-2,1-benzothiazines as potential precursors to P,N type ligands for metals. Accordingly, we reacted S-2-halophenyl-S-methylsulfoximines with 2-bromobenzaldehydes using the Buchwald-Hartwig reaction under conditions previously developed in our laboratory. We found that 2-halophenylmethyl sulfoximines show lower reactivity in process than methylphenyl sulfoximine. Among the 2-(S)-2-halophenyl-(S)-methylsulfoximines tested, S-2-fluorophenyl-S-methyl sulfoximine afforded higher yields of benzothiazines than the bromine- or chlorine-substituted congeners. In the coupling of S-2-halophenyl-S-methylsulfoximines to 2-bromobenzaldehyde, using Ruphos as a ligand gave the best yields.

Sulfoximines Assisted Rh(III)-Catalyzed C-H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines

A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh(III)-catalyzed C-H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.

Synthesis of NH-Sulfoximines by Using Recyclable Hypervalent Iodine(III) Reagents under Aqueous Micellar Conditions

The synthesis of NH-sulfoximines from sulfides has been first developed under mild conditions in an aqueous solution with surfactant TPGS-750-M as the catalyst at room temperature. In this newly developed process, a simple and convenient recycling strategy to regenerate the indispensable hypervalent iodine(III) is used. The resulting 1,2,3-trifluoro-5-iodobezene can be recovered almost quantitively from the mixture by liquid–liquid extraction and then oxidized to give the corresponding iodine(III) species. This optimized procedure is compatible with a broad range of functional groups and can be easily performed on a gram scale, providing a green protocol for the synthesis of sulfoximines.

Sulfoximines-assisted Rh(III)-catalyzed C-H activation and intramolecular annulation for the synthesis of fused isochromeno-1,2-benzothiazines scaffolds under room temperature

Amild and facile Cp?Rh(III)-catalyzed C-Hactivation and intramolecular cascade annulation protocol has been proposed for the furnishing of highly fused isochromeno-1,2-benzothiazines scaffolds using S-phenylsulfoximides and 4-diazoisochroman-3-imine as substrates under room temperature. This method features diverse substituents and functional groups tolerance and relatively mild reaction conditions with moderate to excellent yields. Additionally, retentive configuration of sulfoximides in the conversion has been verified.

Efficient Kinetic Resolution of Sulfur-Stereogenic Sulfoximines by Exploiting CpXRhIII-Catalyzed C?H Functionalization

Chiral sulfoximines with stereogenic sulfur atoms are promising motifs in drug discovery. We report an efficient method to access chiral sulfoximines through a C?H functionalization based kinetic resolution. A rhodium(III) complex equipped with a chiral Cpx ligand selectively participates in conjunction with phthaloyl phenylalanine in the C?H activation of just one of the two sulfoximine enantiomers. The intermediate reacts with various diazo compounds, providing access to chiral 1,2-benzothiazines with synthetically valuable substitution patterns. Both sulfoximines and 1,2-benzothiazines were obtained in high yields and excellent enantioselectivity, with s-values of up to 200. The utility of the method is illustrated by the synthesis of the key intermediates of two pharmacologically relevant kinase inhibitors.

Pd/Norbornene Collaborative Catalysis on the Divergent Preparation of Heterocyclic Sulfoximine Frameworks

Pd/Norbornene cocatalyzed tandem C-H activation/annulation reactions of free NH-sulfoximines with aryl iodides to produce diverse polyheterocyclic sulfoximines in highly chemoselective models are reported. The reaction tolerated a broad range of functiona

Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides

Free NH-sulfoximines were directly prepared from sulfoxides through iron catalysis by applying a readily available, shelf-stable hydroxylamine triflic acid salt. No additional oxidant is needed, and the substrate scope is broad, including a range of heter

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.