cas 4381-25-3, (methylsulfonimidoyl)benzene

Articles about 4381-25-3Total 79 be found

Article title
Article abstract
Author
Journal number and time
Download

Iron-Catalyzed Amination of Sulfides and Sulfoxides with Azides in Photochemical Continuous Flow Synthesis
A photochemical (UVA) continuous flow process for the amination of thioethers and sulfoxides was performed with trichloroethoxysulfonyl azide in the presence of catalytic iron(III) acetylacetonate. Aromatic and aliphatic sulfilimines and sulfoximines were produced in high yields and short reaction times. The reaction with chiral sulfoxides was stereospecific, producing enantioenriched sulfoximines in excellent yields.
Lebel, Hélène,Piras, Henri,Borduy, Marie
p. 1109 - 1112
(2016)
Read Online

Metal-free imination of sulfoxides and sulfides
Using a nitrogen transfer agent obtained in situ by mixing of NsNH 2 and PhI(OAc)2, various N-nosyl sulfoximines and N-nosyl sulfilimines have been prepared under metal-free conditions starting from the corresponding sulfoxides and s
Cho, Gae Young,Bolm, Carsten
p. 8007 - 8008
(2005)
Read Online

Synthesis and bioactivity of new phosphorylated R,R′-substituted sulfoximines
R,R′-disubstituted sulfoximines were phosphorylated with O,O-diethylchloro phosphate and phosphorothionate to obtain new organophosphorus compounds. After purification they were characterized by GC-MS and 1H-NMR. The toxicity of the synthesized
Bellozas, Monica,De Licastro, Susana Arnstein
p. 1369 - 1376
(2005)
Read Online

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.
Kong, Xianqiang,Lin, Long,Chen, Xiaohui,Chen, Yiyi,Wang, Wei,Xu, Bo
p. 3277 - 3282
(2021/07/26)

Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes
An efficient electrochemical flow process for the selective oxidation of sulfides to sulfoxides and sulfones and of sulfoxides toN-cyanosulfoximines has been developed. In total, 69 examples of sulfoxides, sulfones, andN-cyanosulfoximines have been synthesized in good to excellent yields and with high current efficiencies. The synthesis was assisted and facilitated through a supporting electrolyte-free, fully automated electrochemical protocol that highlights the advantages of flow electrolysis.
Amri, Nasser,Wirth, Thomas
p. 15961 - 15972
(2021/07/20)

Chiral Dibenzopentalene-Based Conjugated Nanohoops through Stereoselective Synthesis
Conjugated nanohoops allow to investigate the effect of radial conjugation and bending on the involved π-systems. They can possess unexpected optoelectronic properties and their radially oriented π-system makes them attractive for host–guest chemistry. Be
Hermann, Mathias,Wassy, Daniel,Kohn, Julia,Seitz, Philipp,Betschart, Martin U.,Grimme, Stefan,Esser, Birgit
p. 10680 - 10689
(2021/04/02)

Sulfur-Based Chiral Iodoarenes: An Underexplored Class of Chiral Hypervalent Iodine Reagents
Chiral hypervalent iodine reagents are active players in modern stereoselective organic synthesis. Structurally diverse chiral hypervalent iodine reagents have been synthesised and extensively studied, but hypervalent iodine reagents containing chiral sul
Alharbi, Haifa,Elsherbini, Mohamed,Karam, Fatemah,Osi, Arnaud,Wirth, Thomas
(2021/06/21)

Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C-H Functionalization Enabled by Chiral Carboxylic Acid
Ru(II)-catalyzed enantioselective C-H functionalization involving an enantiodetermining C-H cleavage step remains undeveloped. Here we describe a Ru(II)-catalyzed enantioselective C-H activation/annulation of sulfoximines with α-carbonyl sulfoxonium ylides using a novel class of chiral binaphthyl monocarboxylic acids as chiral ligands, which can be easily and modularly prepared from 1,1′-binaphthyl-2,2′-dicarboxylic acid. A broad range of sulfur-stereogenic sulfoximines were prepared in high yields with excellent enantioselectivities (up to 99% yield and 99% ee) via desymmetrization, kinetic resolution, and parallel kinetic resolution. Furthermore, the resolution products can be easily transformed to chiral sulfoxides and key intermediates for kinase inhibitors.
Zhou, Tao,Qian, Pu-Fan,Li, Jun-Yi,Zhou, Yi-Bo,Li, Hao-Chen,Chen, Hao-Yu,Shi, Bing-Feng
supporting information
p. 6810 - 6816
(2021/05/29)

Synthesis and Configurational Assignment of Vinyl Sulfoximines and Sulfonimidamides
Vinyl sulfones and sulfonamides are valued for their use as electrophilic warheads in covalent protein inhibitors. Conversely, the S(VI) aza-isosteres thereof, vinyl sulfoximines and sulfonimidamides, are far less studied and have yet to be applied to the field of protein bioconjugation. Herein, we report a range of different synthetic methodologies for constructing vinyl sulfoximine and vinyl sulfonimidamide architectures that allows access to new areas of electrophilic chemical space. We demonstrate how late-stage functionalization can be applied to these motifs to incorporate alkyne tags, generating fully functionalized probes for future chemical biology applications. Finally, we establish a workflow for determining the absolute configuration of enantioenriched vinyl sulfoximines and sulfonimidamides by comparing experimentally and computationally determined electronic circular dichroism spectra, enabling access to configurationally assigned enantiomeric pairs by separation.
Craven, Gregory B.,Briggs, Edward L.,Zammit, Charlotte M.,McDermott, Alexander,Greed, Stephanie,Affron, Dominic P.,Leinfellner, Charlotte,Cudmore, Hannah R.,Tweedy, Ruth R.,Luisi, Renzo,Bull, James A.,Armstrong, Alan
p. 7403 - 7424
(2021/06/25)

Novel NH - sulfoxide imine compound and synthesis method thereof
The invention discloses a novel NH - sulfoxide imine compound and a synthesis method thereof, the novel NH - sulfoxide imine compound widens the kind of NH - sulfoxide imine compounds and lays a foundation for synthesis of a NH - sulfoxide imine skeleton
-
Paragraph 0027-0030

(2021/09/21)

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.
Liu, Dong,Liu, Zhao-Ran,Ma, Cong,Jiao, Ke-Jin,Sun, Bing,Wei, Lei,Lefranc, Julien,Herbert, Simon,Mei, Tian-Sheng
supporting information
p. 9444 - 9449
(2021/03/29)

One-Pot Synthesis of N-Iodo Sulfoximines from Sulfides
This is the first report on the synthesis and characterization of N-iodo sulfoximines. The synthesis was designed as a room temperature one-pot cascade reaction from readily available sulfides as starting compounds, converted into sulfoximines by reaction with ammonium carbonate and (diacetoxyiodo)benzene, followed by iodination with N-iodosuccinimide or iodine in situ, in up to 90% isolated yields, also at a multigram scale. Iodination of aryls with N-iodo sulfoximines, oxidation, and conversion to N-SCF3 congeners have been demonstrated.
Zupanc, An?e,Jereb, Marjan
p. 5991 - 6000
(2021/05/05)

Blue light-promoted radical sulfoximido-chalcogenization of aliphatic and aromatic alkenes
A transition metal-free synthesis ofN-(arylthio/seleno)ethyl sulfoxidminesviablue light-promoted radical sulfoximido-chalcogenization of aliphatic and aromatic alkenes was developed. The sulfoximidation process demonstrated high chemoselectivity and allowed a broad substrate scope, completing the sulfoximido-chalcogenization of alkenes in good yields.
Chen, Hongyi,Chen, Li,He, Ze,Zeng, Qingle
supporting information
p. 2624 - 2627
(2021/04/21)

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.
Li, Jian,Li, Hui,Fang, Daqing,Liu, Lingjun,Han, Xu,Sun, Jina,Li, Chunpu,Zhou, Yu,Ye, Deju,Liu, Hong
p. 15217 - 15227
(2021/10/25)

General Method for the Asymmetric Synthesis of N-H Sulfoximines via C-S Bond Formation
A versatile method for the synthesis of enantioenriched N-H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily removed from the resultant sulfoximines via an unusual oxidative debenzylation protocol that utilizes molecular oxygen as the terminal oxidant. This provides a general strategy for the synthesis of highly enantioenriched N-H sulfoximines.
Argent, Stephen P.,Lewis, William,Mendon?a Matos, Priscilla,Moore, Jonathan c.,Stockman, Robert A.
(2020/03/30)

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.
Zhang, Guocai,Tan, Hongsheng,Chen, Weichun,Shen, Hong C.,Lu, Yue,Zheng, Changwu,Xu, Hongxi
p. 922 - 928
(2020/02/20)

Palladium-Catalyzed Oxidative Annulation of Sulfoximines and Arynes by C-H Functionalization as an Approach to Dibenzothiazines
This work reports a novel and efficient palladium-catalyzed synthesis of tricyclic dibenzothiazines using easily prepared aryl sulfoximines and aryne precursors via C-H functionalization and cyclization. A mechanistic investigation indicated that the C-H bond cleavage at the position ortho to the sulfoximine group is the rate-determining step.
Li, Jing,Li, Shan,Liu, Liansheng,Wang, Rong,Wei, Junfa,Yang, Yihui
supporting information
p. 7470 - 7474
(2020/10/09)

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.
Han, Xu,Li, Chunpu,Li, Jian,Liu, Hong,Wang, Bao
(2020/06/29)

Design, synthesis and antiplasmodial evaluation of sulfoximine-triazole hybrids as potential antimalarial prototypes
Background: Malaria, caused by the deadly Plasmodium falciparum strain, claims the lives of millions of people annually. The emergence of drug-resistant strains of P. falciparum to the artemisinin-based combination therapy (ACT), the last line of defense against malaria, is worrisome and urges for the development of new chemo-types with a new mode of action. In the search of new antimalarial agents, hybrids of triazoles and other known antimalarial drugs have been reported to possess better activity than either of the parent compounds administered individually. Despite their better activity, no hybrid antimalarial drugs have been developed so far. Objective: In the hope of developing new antimalarial prototypes, we propose the design, synthesis and antimalarial evaluation of novel sulfoximine-triazole hybrids owing to their interesting biological and physiological properties. Method: The sulfoximine part of the hybrid will be synthesized via imidation of the corresponding sulfoxide. Propargylation of the NH moiety of the sulfoximine followed by copper-catalyzed click chemistry with benzyl azide was envisaged to provide the target sulfoximine-triazole hybrids. Results: Five novel sulfoximine-triazole hybrids possessing various substituents on the sulfoximine moiety have been successfully synthesized and evaluated for their antiplasmodial and cytotoxicity activities. The results revealed that the co-presence of the sulfoximine and triazole moieties along with a lipophilic alkyl substituent on the sulfur atom impart significant activity. Conclusion: Sulfoximine-triazole hybrids could be used as a prototype for the synthesis of new derivatives with better antiplasmodial activities.
Mabasa, Tommy Fredrick,Awe, Babatunde,Laming, Dustin,Kinfe, Henok Hadgu
p. 683 - 690
(2019/08/30)

N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity
Herein we demonstrate the expanded utility of a recently described N-trifluoromethylthiolation protocol to sulfonimidamide containing substances. The novel N-trifluoromethylthio sulfonimidamide derivatives thus obtained were evaluated for antibacterial activity against Mycobacterium tuberculosis (M. tb.) and Mycobacterium abscessus and Gram + Ve (Streptococcus aureus, Bacillus subtilis), and Gram - Ve (Escherichia coli, Pseudomonas aeruginosa) bacteria. Two compounds, 13 and 15 showed high antimycobacterial activity with MIC value of 4-8 μg/mL; i.e. comparable to WHO recommended first line antibiotic for TB infection ethambutol. The same compounds were also found to be cytotoxic in HepG2 cells (compound 13 IC50 = 15 μg/mL; compound 15 IC50 = 65 μg/mL). A structure activity relationship, using matched pair analysis, gave the unexpected conclusion that the trifluoromethylthio moiety was responsible for the cellular and bacterial toxicity. Given the increasing use of the trifluoromethylthio group in contemporary medicinal chemistry, this observation calls for considerations before implementation of the functionality in drug design.
Thota, Niranjan,Makam, Parameshwar,Rajbongshi, Kamal K.,Nagiah, Savania,Abdul, Naeem Sheik,Chuturgoon, Anil A,Kaushik, Amit,Lamichhane, Gyanu,Somboro, Anou M.,Kruger, Hendrik G.,Govender, Thavendran,Naicker, Tricia,Arvidsson, Per I
supporting information
p. 1457 - 1461
(2019/10/11)

Synthesis of Sulfonimidamides from Sulfenamides via an Alkoxy-amino-λ6-sulfanenitrile Intermediate
Sulfonimidamides are intriguing new motifs for medicinal and agrochemistry, and provide attractive bioisosteres for sulfonamides. However, there remain few operationally simple methods for their preparation. Here, the synthesis of NH-sulfonimidamides is achieved directly from sulfenamides, themselves readily formed in one step from amines and disulfides. A highly chemoselective and one-pot NH and O transfer is developed, mediated by PhIO in iPrOH, using ammonium carbamate as the NH source, and in the presence of 1 equivalent of acetic acid. A wide range of functional groups are tolerated under the developed reaction conditions, which also enables the functionalization of the antidepressants desipramine and fluoxetine and the preparation of an aza analogue of the drug probenecid. The reaction is shown to proceed via different and concurrent mechanistic pathways, including the formation of novel S≡N sulfanenitrile species as intermediates. Several alkoxy-amino-λ6-sulfanenitriles are prepared with different alcohols, and shown to be alkylating agents to a range of nucleophiles.
Briggs, Edward L.,Tota, Arianna,Colella, Marco,Degennaro, Leonardo,Luisi, Renzo,Bull, James A.
supporting information
p. 14303 - 14310
(2019/09/06)

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.
Brauns, Marcus,Cramer, Nicolai
p. 8902 - 8906
(2019/06/04)

Copper-catalyzed imination of sulfoxides and sulfides
Sulfoximines and sulfilimines have attracted considerable interest among organic chemists. The Cu(II)-catalyzed imination of sulfoxides and sulfides using various N-fluoro benzenesulfonamides was investigated in this study. The scope of the reaction was demonstrated by using several substituted sulfides and sulfoxides. The flow strategy for the preparation of NH-sulfoximines was also examined. By trapping nitrene intermediates through triphenylphosphine, we found that the reaction was conducted through a metal-nitrene intermediate mechanism.
Liu, Yuanyuan,Wang, Hanying,Yang, Xianjin
p. 4697 - 4702
(2019/07/22)

Batch and Continuous-Flow Iron(II)-Catalyzed Synthesis of Sulfilimines and Sulfoximines using N-Mesyloxycarbamates
The synthesis of sulfilimines and sulfoximines with N-mesyloxycarbamates in presence of catalytic iron(II) chloride hydrate is described. The use of 1-butylimidazole as a base proved instrumental in enabling a homogeneous reaction mixture compatible with continuous flow processes. The amination is applicable to a wide range of substrates, and affords the desired product in good to excellent yields within 1 to 60 minutes.
Lai, Calvine,Mathieu, Gary,Gabrielli Tabarez, Lucia Paola,Lebel, Hélène
supporting information
p. 9423 - 9426
(2019/05/21)

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
Yu, Hao,Li, Zhen,Bolm, Carsten
supporting information
p. 324 - 327
(2017/12/15)

Persulfate-promoted oxidative C-N bond coupling of quinoxalinones and: NH -sulfoximines
The persulfate-meditated oxidative C-N bond coupling of the C-H bond of quinoxalinones and the N-H bond of NH-sulfoximines is reported. The reaction proceeds smoothly under transition metal-free conditions and provides good to excellent yields of sulfoximidoyl-functionalized quinoxalinone products under mild conditions. The optimized conditions were found to be suitable for a range of sulfoximine and quinoxalinone substrates. This reaction offers a new and convenient strategy to directly install the sulfoximine moiety into the C3 position of quinoxalinone.
Sumunnee, Ladawan,Pimpasri, Chaleena,Noikham, Medena,Yotphan, Sirilata
supporting information
p. 2697 - 2704
(2018/04/27)

Enantiopure sulfoximines-catalyzed 1, 4-additions to 2-en-ketone
An efficient chiral catalyst procedure for the preparation of β-chiral ketone via the 1, 4-additions reaction of 2-en-ketone has been developed using enantiopure sulfoximines modified with functional groups as ligands. The carefully design and synthesized
Zhao, Hongwei,Han, Hui,Yang, Hengquan,wang, Li
p. 210 - 213
(2018/06/26)

Direct C(sp2)?H Hydroxylation of Arenes with Palladium(II)/Oxygen Using Sulfoximines as a Recyclable Directing Group
The aerobic palladium(II) catalysis presented herein offers facile entry to various substituted phenols through site-selective C?H hydroxylation of arenes by using sulfoximines as a reusable directing group. The notable aspects of our method include the use of molecular oxygen (O2) as the sole oxidant, the activation of molecular oxygen through aldehyde autoxidation, operational simplicity, and the mechanistic studies into the catalytic C?H hydroxylation process.
Das, Prasenjit,Guin, Joyram
p. 2370 - 2373
(2018/04/25)

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.
Wang, Tao,Wang, Yi-Ning,Wang, Rui,Wang, Xi-Sheng
supporting information
p. 2449 - 2452
(2018/08/17)

Ru (II)-Catalyzed Coupling-Cyclization of Sulfoximines with alpha-Carbonyl Sulfoxonium Ylides as an Approach to 1,2-Benzothiazines
A Ru(II)-catalyzed approach for the rapid assembly of 1,2-benzothiazines has been developed to enable the coupling-cyclization of aryl Csp2?H bonds with α-carbonyl sulfoxonium ylides via Csp2?H activation process. The present method could be further applied to the construction of the 4-substituted 1,2-benzothiazine skeletons. (Figure presented.).
Xie, Haisheng,Lan, Jianyong,Gui, Jiao,Chen, Fengjuan,Jiang, Huangfeng,Zeng, Wei
p. 3534 - 3543
(2018/08/06)

Eaton's reagent-mediated metal-free and efficient synthesis of NH-sulfoximines
NH-sulfoximines can be prepared efficiently from corresponding sulfoxides in the presence of sodium azide and Eaton's reagent. This metal-free and efficient methodology is applicable to a wide variety of functionalized sulfoxides to afford NH-sulfoximines in good to excellent yields with shorter reaction time than previously reported methods.
Wang, Jianping,Zhang, Jian,Miao, Kun,Yun, Hongying,Shen, Hong C.,Zhao, Weili,Liang, Chungen
supporting information
p. 333 - 337
(2017/01/03)

A Convenient, Mild, and Green Synthesis of NH-Sulfoximines in Flow Reactors
NH-sulfoximines are emerging as useful and important targets in drug discovery and synthetic organic chemistry. We report herein the development of an efficient, convenient, and sustainable continuous-flow strategy, for the direct, straightforward preparation of NH-sulfoximines by using sulfides or sulfoxides as suitable starting material. The flow process uses PhI(OAc)2 as the oxidant and aqueous solutions of ammonia as the N source. The scope of the reaction has been demonstrated by using several substituted sulfides and sulfoxides including enantioenriched and biologically relevant starting materials. The flow strategy was found to be more convenient with respect to conventional batch processing.
Degennaro, Leonardo,Tota, Arianna,De Angelis, Sonia,Andresini, Michael,Cardellicchio, Cosimo,Capozzi, Maria Annunziata,Romanazzi, Giuseppe,Luisi, Renzo
supporting information
p. 6486 - 6490
(2017/09/13)

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.
Pimpasri, Chaleena,Sumunnee, Ladawan,Yotphan, Sirilata
supporting information
p. 4320 - 4327
(2017/07/10)

Direct: N -acylation of sulfoximines with carboxylic acids catalyzed by the B3NO2 heterocycle
In contrast to recent significant progress in the development of catalytic methodologies for nitrogen acylations, syntheses of N-acyl sulfoximines have been slow to evolve, and still largely rely on the use of stoichiometric amounts of activating reagents
Noda, Hidetoshi,Asada, Yasuko,Shibasaki, Masakatsu,Kumagai, Naoya
supporting information
p. 7447 - 7450
(2017/07/12)

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.
Gupta, Surabhi,Chaudhary, Priyanka,Muniyappan, Nalluchamy,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
supporting information
p. 8493 - 8498
(2017/10/27)

Ruthenium(II)-Catalyzed C-H Oxygenations of Reusable Sulfoximine Benzamides
C-H oxygenations of synthetically meaningful sulfoximine benzamides were accomplished by a versatile ruthenium catalysis regime. The ruthenium(II) catalyst was characterized by excellent mono- and chemoselectivity as well as positional selectivity via facile base-assisted intramolecular electrophilic substitution-type (BIES) C-H activation. The synthetic utility of the approach was reflected by high functional group tolerance and sulfoximine removal in a traceless fashion.
Raghuvanshi, Keshav,Zell, Daniel,Ackermann, Lutz
supporting information
p. 1278 - 1281
(2017/03/22)

Mechanistic investigation of the NH-sulfoximination of sulfide. Evidence for λ6-sulfanenitrile intermediates
We report a new procedure for the preparation of NH-sulfoximines from sulfides using PIDA as an oxidant and ammonium carbamate as the ammonia source. Excellent yields were obtained with a wide range of sulfides. The formation of acetoxy- and methoxy-λsup
Lohier, Jean-Fran?ois,Glachet, Thomas,Marzag, Hamid,Gaumont, Annie-Claude,Reboul, Vincent
supporting information
p. 2064 - 2067
(2017/02/15)

Method for synthesizing sulfoximine compounds from thioether
The invention discloses a synthetic method for synthesizing sulfoximine compounds from thioether in one step and application thereof. The synthetic method disclosed by the invention comprises the step of mixing the thioether, an ammonia source and an organic solvent together for carrying out an oxidizing reaction in the presence of an oxidizing agent, thereby obtaining the corresponding sulfoximine compounds. According to the invention, one-step synthesis of the sulfoximine compounds from the thioether is realized for the first time. In recent years, the sulfoximine structure is introduced into the existing drug molecules or high-activity compound molecules, and many high-activity molecules at the clinical stage and listed drug molecules appear. According to the method disclosed by the invention, the drug molecules containing the sulfoximine structure are produced, and the industrial cost can be greatly reduced; and moreover, the synthetic method provided by the invention has the advantages of being high in yield, readily available in raw materials, simple in conditions, simple in reaction equipment, easy in industrialized production, and the like. The structural formula is as shown in the specification.
-
Paragraph 0017; 0018

(2017/08/28)

Reactions of organoboranes with carbanions bearing three potential leaving groups: unusual processes, products and mechanisms
Known reagents that transfer three alkyl groups of a trialkylborane intramolecularly to a single carbon atom lack features to influence stereochemistry. We have investigated four reagents of type LiCCl2X, where X might be amenable to variation. All behaved differently. With X=OR (R=cyclohexyl, menthyl), the reagent decomposed, leading to only low yields of triple migration products. With X=S(O)Ph, a single migration occurred, followed by isomerisation to boron enolate-like species that hydrolysed to α-chloroalkyl phenyl sulfoxides or reacted with aldehydes to aldol-like products. With X=SO2Ph, the major product was the corresponding α,α-dichloroalkyl phenyl sulfone, apparently formed through a redox reaction. With X=S(O)(NMe)Ph, products of three intramolecular alkyl migrations were obtained with unhindered trialkylboranes. Attempts have been made to gain understanding of the sulfoxide process by investigating proportions of aldol-like products, using X-ray crystallography and ab initio calculations.
Saleh, Basil A.,Smith, Keith,Elliott, Mark C.,Jones, D. Heulyn,Kariuki, Benson M.,El Hiti, Gamal A.
p. 6914 - 6928
(2016/10/14)

Preparation and Isolation of a Chiral Methandiide and Its Application as Cooperative Ligand in Bond Activation
The activation of element-hydrogen bonds by means of metal-ligand cooperation has received increasing attention as alternative to classical activation processes, which exclusively occur at the metal center. Carbene complexes derived from methandiide precu
Feichtner, Kai-Stephan,Englert, Simon,Gessner, Viktoria H.
supporting information
p. 506 - 510
(2016/01/15)

Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines
Herein, we report a simple and metal-free method for the synthesis of N-azine sulfoximines by the nucleophilic substitution of azine N-oxides with NH-sulfoximines. The present method works at room temperature with wide functional group compatibility and gives several unprecedented N-azine sulfoximines. The reaction conditions were also found suitable with enantiopure substrates and furnished products without any racemization. It also finds an application in the sulfoximination of azine-based functional molecules such as 2,2′-bipyridine, 1,10-phenanthroline, and quinine.
Aithagani, Sravan Kumar,Kumar, Mukesh,Yadav, Mahipal,Vishwakarma, Ram A.,Singh, Parvinder Pal
p. 5886 - 5894
(2016/07/23)

Copper-catalyzed: N -thioetherification of sulfoximines using disulfides
A novel copper-catalyzed N-thioetherification of sulfoximines under mild reaction conditions was developed. In this procedure, the N-S bond formation was achieved using readily available disulfides as the sulfur source.
Zhu, Hui,Yu, Jin-Tao,Cheng, Jiang
supporting information
p. 11908 - 11911
(2016/10/11)

Organocatalytic Kinetic Resolution of Sulfoximines
An efficient kinetic resolution of sulfoximines with enals was realized using chiral N-heterocyclic carbene (NHC) catalysts. The stereoselective amidation proceeds without additional acyl transfer agent. Both enantiomers of the sulfoximines can be obtaine
Dong, Shunxi,Frings, Marcus,Cheng, Hanchao,Wen, Jian,Zhang, Duo,Raabe, Gerhard,Bolm, Carsten
supporting information
p. 2166 - 2169
(2016/03/05)

Ruthenium-Catalyzed Hydroarylation and One-Pot Twofold Unsymmetrical C?H Functionalization of Arenes
A methyl phenyl sulfoximine (MPS) is used as a directing group in the ruthenium-catalyzed intramolecular hydroarylation of alkene-tethered benzoic acid derivatives to afford dihydrobenzofurans and indolines in good to excellent yields. A one-pot, unsymmetrical, twofold C?H functionalization involving intramolecular C?C and intermolecular C?C/C?N bond formations is successfully demonstrated by using a single set of catalytic reaction conditions, which is unprecedented thus far. A novel isoquinolone-bearing dihydrobenzofuran is constructed through an unsymmetrical twofold C?H functionalization.
Ghosh, Koushik,Ramesh, E.,Rit, Raja K.,Sahoo, Akhila K.
supporting information
p. 7821 - 7825
(2016/07/07)

Method for oxidizing sulfilimine into sulfoximide
The invention provides a method for oxidizing sulfilimine into sulfoximide. The method comprises the following steps: preparing a tungsten oxide WO3-x nanosheet catalyst, and carrying out WO3-x nanosheet catalyzed oxidation of sulfilimine. The method has
-
Paragraph 0043; 0044; 0045; 0046; 0047; 0048; 0049

(2016/11/09)

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.
Aithagani, Sravan Kumar,Dara, Saidulu,Munagala, Gurunadham,Aruri, Hariprasad,Yadav, Mahipal,Sharma, Shweta,Vishwakarma, Ram A.,Singh, Parvinder Pal
supporting information
p. 5547 - 5549
(2015/12/01)

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.
Lamers, Philip,Priebbenow, Daniel L.,Bolm, Carsten
p. 5594 - 5602
(2015/09/01)

Ruthenium-catalyzed ortho -C-H mono- and di-imidation of arenes with n -tosyloxyphthalimide
The Ru(II)-catalyzed imidation of the o-C-H bond in arenes with N-tosyloxyphthalimide is realized with the assistance of a methyl phenylsulfoximine (MPS) directing group. This method is applicable to access the hitherto difficult o-C-H di-imidation produc
Yadav, M. Ramu,Shankar, Majji,Ramesh,Ghosh, Koushik,Sahoo, Akhila K.
supporting information
p. 1886 - 1889
(2015/04/27)

Asymmetric synthesis of γ-lactones through reaction of sulfoxonium ylides, aldehydes, and ketenes
A method for the enantioselective synthesis of γ-lactones through the reaction of enantioenriched sulfoxonium ylides, aldehydes, and ketenes was developed. Enantioenriched (98% ee) aminosulfoxonium ylide was subjected to reaction with a variety of aldehydes (both aromatic and aliphatic) and disubstituted ketenes, leading to the formation of α,β-substituted γ-lactones in moderate to very good diastereoselectivity (dr up to 95:5) and with enantiomeric excesses of up to 79% ee. Best levels of enantioselectivity were observed in the reactions of enantioenriched aminosulfoxonium ylide with isobutyraldehyde and various alkylarylketenes.
Peraino, Nicholas J.,Ho, Han-Jen,Mondal, Mukulesh,Kerrigan, Nessan J.
p. 4260 - 4263
(2014/07/22)

Rhodium-catalyzed direct synthesis of unprotected NH-sulfoximines from sulfoxides
A novel rhodium-catalyzed imination of sulfoxides using O-(2,4-dinitrophenyl)hydroxylamine is developed under mild conditions with good functional group tolerance. This method provides an efficient access to free NH-sulfoximines, an important structural u
Miao, Jinmin,Richards, Nigel G. J.,Ge, Haibo
supporting information
p. 9687 - 9689
(2014/08/18)

N-arylations of sulfoximines with 2-arylpyridines by copper-mediated dual N-H/C-H activation
A high-yielding method providing rapid access to new N-arylated sulfoximines has been developed. A stoichiometric amount of copper facilitates the C-H activation of 2-arylpyridines which then undergo oxidative C-N cross-couplings with various sulfoximine derivatives.
Wang, Long,Priebbenow, Daniel L.,Dong, Wanrong,Bolm, Carsten
supporting information
p. 2661 - 2663
(2014/06/09)

Sulfoximine-directed ruthenium-catalyzed ortho -C-H Alkenylation of (Hetero)Arenes: Synthesis of EP3 receptor antagonist analogue
The reusable sulfoximine directing-group-assisted Ru(II)-catalyzed chemo- and regioselective ortho-C-H alkenylation of arenes and heteroarenes with acrylates and α,β-unsaturated ketones/vinyl sulfone is shown. The N-aroyl sulfoximine undergoes annulation with diphenylacetylene, delivering isoquinolinones and methyl phenyl sulfoxide. The present protocol is successfully employed for the synthesis of the EP3 receptor antagonist analogue.
Yadav, M. Ramu,Rit, Raja K.,Shankar, Majji,Sahoo, Akhila K.
p. 6123 - 6134
(2014/07/21)