- Rhodium(iii)-catalyzed cascade C-H functionalization/annulation of sulfoximines with iodonium ylides for the synthesis of cyclohexanone-1,2-benzothiazines
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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
- Chen, Lu,Hao, Liqiang,Ji, Yafei,Wang, Yangyang,Wang, Zhichao,Wu, Gaorong,Xu, Xiaobo
-
supporting information
p. 887 - 894
(2022/02/03)
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- Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes
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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
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p. 15961 - 15972
(2021/07/20)
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- Electrochemical Oxidative Syntheses of NH-Sulfoximines, NH-Sulfonimidamides and Dibenzothiazines via Anodically Generated Hypervalent Iodine Intermediates
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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
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p. 3277 - 3282
(2021/07/26)
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- Nickel-Catalyzed N-Arylation of NH-Sulfoximines with Aryl Halides via Paired Electrolysis
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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
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supporting information
p. 9444 - 9449
(2021/03/29)
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- Blue light-promoted radical sulfoximido-chalcogenization of aliphatic and aromatic alkenes
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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
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supporting information
p. 2624 - 2627
(2021/04/21)
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- Sulfoximines Assisted Rh(III)-Catalyzed C-H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines
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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
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p. 15217 - 15227
(2021/10/25)
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- Synthesis and Configurational Assignment of Vinyl Sulfoximines and Sulfonimidamides
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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
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p. 7403 - 7424
(2021/06/25)
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- Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C-H Functionalization Enabled by Chiral Carboxylic Acid
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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)
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- Synthesis of NH-Sulfoximines by Using Recyclable Hypervalent Iodine(III) Reagents under Aqueous Micellar Conditions
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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
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p. 922 - 928
(2020/02/20)
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- Palladium-Catalyzed Oxidative Annulation of Sulfoximines and Arynes by C-H Functionalization as an Approach to Dibenzothiazines
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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
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supporting information
p. 7470 - 7474
(2020/10/09)
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- 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
-
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- Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides
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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)
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- 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)
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- 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
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p. 3534 - 3543
(2018/08/06)
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- Straightforward Strategies for the Preparation of NH-Sulfox-imines: A Serendipitous Story
-
Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected 'free' NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches. 1 Introduction 2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts 3 Metal-Free Strategies to Prepare NH-Sulfoximines 4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides 5 Further Applications 6 Conclusion.
- Bull, James A.,Degennaro, Leonardo,Luisi, Renzo
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p. 2525 - 2538
(2017/11/28)
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- 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
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supporting information
p. 333 - 337
(2017/01/03)
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- 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
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supporting information
p. 8493 - 8498
(2017/10/27)
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- Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers
-
Direct synthesis of NH-sulfoximines from sulfides has been achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction is mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-so
- Tota, Arianna,Zenzola, Marina,Chawner, Stephen J.,John-Campbell, Sahra St,Carlucci, Claudia,Romanazzi, Giuseppe,Degennaro, Leonardo,Bull, James A.,Luisi, Renzo
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supporting information
p. 348 - 351
(2017/01/03)
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- 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
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supporting information
p. 6486 - 6490
(2017/09/13)
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- Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides
-
A new system for NH transfer is developed for the preparation of sulfoximines, which are emerging as valuable motifs for drug discovery. The protocol employs readily available sources of nitrogen without the requirement for either preactivation or for met
- Zenzola, Marina,Doran, Robert,Degennaro, Leonardo,Luisi, Renzo,Bull, James A.
-
supporting information
p. 7203 - 7207
(2016/07/06)
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- 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)
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- Synthesis of Sulfoximine Carbamates by Rhodium-Catalyzed Nitrene Transfer of Carbamates to Sulfoxides
-
Sulfoximines are of considerable interest for incorporation into medicinal compounds. A convenient synthesis of N-protected sulfoximines is achieved, under mild conditions, by rhodium-catalyzed transfer of carbamates to sulfoxides. The first examples of 4-membered thietane-oximines are prepared. Sulfoximines bearing Boc and Cbz groups are stable to further cross coupling reactions, and readily deprotected. This method may facilitate the preparation of NH-sulfoximines providing improved (global) deprotection strategies, which is illustrated in the synthesis of methionine sulfoxide (MSO).
- Zenzola, Marina,Doran, Robert,Luisi, Renzo,Bull, James A.
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p. 6391 - 6399
(2015/06/30)
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- Rhodium-catalyzed direct synthesis of unprotected NH-sulfoximines from sulfoxides
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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)
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- N-arylations of sulfoximines with 2-arylpyridines by copper-mediated dual N-H/C-H activation
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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
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supporting information
p. 2661 - 2663
(2014/06/09)
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- Sulfoxide-to-sulfilimine conversions: Use of modified Burgess-type reagents
-
Sulfoxides can directly be converted into N-cyanosulfilimines using a new Burgess-type reagent. By applying this strategy with a related reagent variant, synthetically valuable NH-sulfoximines have been prepared from sulfoxides via N-protected sulfilimines. The practical three-step reaction sequence is generally high yielding and applicable to a wide range of substrates. The sulfoxide-to-sulfilimine conversion can also be performed under solvent-reduced conditions in a ball mill. Copyright
- Hendriks, Christine M. M.,Lamers, Philip,Engel, Julien,Bolm, Carsten
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p. 3363 - 3368
(2013/12/04)
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- Sulfoximines: A reusable directing group for chemo-and regioselective ortho C-H oxidation of arenes
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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.
- Yadav, M. Ramu,Rit, Raja K.,Sahoo, Akhila K.
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supporting information; experimental part
p. 5541 - 5545
(2012/06/01)
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- Imination of sulfides and sulfoxides with sulfonylimino- λ3-bromane under mild, metal-free conditions
-
Exposure of sulfides and sulfoxides to trifluoromethanesulfonylimino(aryl)- λ3-bromane in dichloromethane at 0°C results in a facile transfer of the sulfonylimino group to sulfur atoms and affords N-triflylsulfilimines and -sulfoximines in high yields under transition-metal-free conditions. Imination of (R)-methyl p-tolyl sulfoxide proceeded with predominant retention of configuration at the stereogenic sulfur center. The Hammett plot afforded ρ values of -0.58 for para-substituted thioanisoles and -0.49 for their equivalent sulfoxides, which suggests a buildup of positive charge on the sulfur atoms of sulfides and sulfoxides in the transition state. Calculations suggest a bimolecular nucleophilic-substitution mechanism on the negatively charged nitrogen atom of the sulfonylimino- λ3-bromane, which involves the attack of a sulfide from the opposite side to bromine(III).
- Ochiai, Masahito,Naito, Masao,Miyamoto, Kazunori,Hayashi, Satoko,Nakanishi, Waro
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supporting information; scheme or table
p. 8713 - 8718
(2010/10/19)
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- SULPHOXIMINE-SUBSTITUTED QUINAZOLINE DERIVATIVES AS IMMUNO-MODULATORS, THEIR PREPARATION AND USE AS MEDICAMENTS
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The present invention relates to sulphoximine-substituted quinazoline derivatives of the formula (I), processes for their preparation and their use as a medicament for the treatment of various diseases.
- -
-
Page/Page column 39
(2009/07/25)
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- Iron(ii) triflate as an efficient catalyst for the imination of sulfoxides
-
The challenging imination of benzyl-, sterically demanding alkyl-, and heteroaryl-substituted sulfoxides has been studied. Iron(II) triflate was identified as a highly efficient and robust catalyst for sulfur imination reactions. A variety of sulfoxides a
- Mancheno, Olga Garcia,Dallimore, Jonathan,Plant, Andrew,Bolm, Carsten
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supporting information; experimental part
p. 2429 - 2432
(2009/10/23)
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- NOVEL SULPHOXIMINE-SUBSTITUTED QUINAZOLINE AND QUINAZOLINE DERIVATIVES AS KINASE INHIBITORS
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The present invention relates to a quinoline or quinazoline derivative having the general formula (A): in which R3, R4, W, Y and Q are indicated in the description and the claims, the use of the compounds of the general formula (A) f
- -
-
Page/Page column 35
(2009/01/20)
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- Stereoselective rhodium-catalyzed lmination of sulfides
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(Chemical Equation Presented) The preparation of optically active sulfilimines via the catalytic diastereoselective imination of sulfides using a chiral nitrene is described. Excellent yields up to 97% and good diastereoselectivities up to 96% have been obtained. Oxidation of the sulfilimines then stereospecifically affords the corresponding sulfoximines with very good yields in the 88-96% range.
- Collet, Florence,Dodd, Robert H.,Dauban, Philippe
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supporting information; experimental part
p. 5473 - 5476
(2009/06/06)
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- Rhodium-catalyzed imination of sulfoxides and sulfides: Efficient preparation of N-unsubstituted sulfoximines and sulfilimines
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The Rh(II)-catalyzed imination of sulfoxides and sulfides using [Rh 2(OAc)4] as a catalyst and trifluoroacetamide or sulfonylamides in combination with iodobenzene diacetate and magnesium oxide affords sulfoximines and sulfilimines, respectively, in a stereospecific manner.
- Okamura, Hiroaki,Bolm, Carsten
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p. 1305 - 1307
(2007/10/03)
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- Geminal bis(sulfoximine)s: Synthesis and applications in asymmetric catalysis
-
A number of C2-symmetrical geminal bis-(sulfoximine)s have been prepared for the first time and used as ligands in boron-mediated reductions of acetophenone and copper complex-catalyzed 1,4-additions of diethylzinc to 2-cyclohexenone. The coppe
- Reggelin,Weinberger,Spohr
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p. 1295 - 1306
(2007/10/03)
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- Electrochemical Imination of Sulfoxides Using N-Aminophthalimide
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(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.
- Siu, Tung,Yudin, Andrei K.
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p. 1839 - 1842
(2007/10/03)
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- A FACILE CONVERSION OF SULFOXIMINES AND SULFONEDIIMINES TO SULFOXIDES AND SULFILIMINES WITH TERT-BUTYL NITRITE
-
N-Unsubstituted sulfoximines and N-mono-tosylsulfonediimines were found to react readily with tert-butyl nitrite to give the corresponding sulfoxides and N-tosylsulfilimines in high yields with no racemization.
- Akutagawa, Kunihiko,Furukawa, Naomichi,Oae, Shigeru
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p. 369 - 374
(2007/10/02)
-