<i>N</i>-Trifluoromethylthiolated Sulfoximines

Bohnen, Christian; Bolm, Carsten

doi:10.1021/acs.orglett.5b01384

Cited by 79 publications

(69 citation statements)

References 46 publications

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“…1 With reference to NH--sulfoximines, the availability of a free nitrogen group offers the possibility to further functionalize a molecule. Methodologies for N--trifluoromethylation, 8 trifluoromethylthiolation, 9 aroylation, 10 intramolecular halocyclization, 11 alkynylation, 12 and alkylation, 13 have increased the available molecular diversity in compounds bearing the sulfoximine group. Very recently, an interesting preparation of optically active of NH--sulfoximines via organocatalytic kinetic resolution has been reported.…”

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confidence: 99%

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

et al. 2017

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Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

et al. 2017

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“…The process can be done in one‐pot fashion. The reaction proceeded successfully with diaryl, aryl alkyl, and dialkyl sulfoximines 162 …”

Section: Synthesis Of Sulfoximines and Their Derivativesmentioning

confidence: 99%

Oxidative Coupling with S–N Bond Formation

2018

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Oxidative strategies are a powerful tool in organic synthesis for the formation of heteroatom–heteroatom, carbon–heteroatom, and carbon–carbon bonds. Among these processes the reactions of oxidative S–N bond formation deserve considerable interest as convenient, effective, and environmentally friendly alternatives to existing methods for the synthesis of a great variety of organic compounds widely used in organic and medicinal chemistry. These transformations take place through the interaction of S‐ and N‐reagents and an oxidant, by radical or ionic mechanisms. Sulfinic acids and their salts, thiols, sulfonyl hydrazides, and thiosulfonates are generally used as S‐reagents; aliphatic and aromatic amines are usually applied as N‐reagents. The role of the oxidant mostly lies in the oxidation of the S‐reagent, after which the formed active species reacts with the N‐reagent to result in the S–N coupling product. There are two versions of oxidative S–N coupling processes: the intermolecular variant opens simple pathways to sulfen‐, sulfin‐, and sulfonamides, sulfenyl‐ and sulfoximines, sulfanes, and sulfur diimides, whereas the intramolecular one leads to the formation of various heterocycles. Of the major problems associated with successful performance of oxidative S–N coupling reactions, the first relates to the search for coupling partners that will work together to form a new bond under oxidative conditions. The second is the choice of a suitable oxidative system that will not overoxidize starting compounds. That is why mild oxidants, such as hypervalent iodine compounds and copper salts and complexes, are generally applied in these processes. This is the first exhaustive review relating to achievements in oxidative transformations involving S–N bond formation. It summarizes 134 references, mainly from 2000 to 2018, and is divided into chapters according to the classes of compounds synthesized.

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“…N-brominated imines have rarely been reported. [22] In summary,aconvenient and functional-group-tolerant silver-catalyzed three-component reaction of terminal alkynes,T MSN 3 ,a nd sodium sulfinates has been developed, which shows broad substrate scope with respect to both the …”

Section: Angewandte Chemiementioning

confidence: 99%

Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes

Ning

Liao

et al. 2017

Angewandte Chemie

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As ilver-catalyzed intermolecular aminosulfonylation of terminal alkynes with sodium sulfinates and TMSN 3 is reported. This three-component reaction proceeds through sequential hydroazidation of the terminal alkyne and addition of as ulfonyl radical to the resultant vinyl azide.T he method enables the stereoselective synthesis of aw ide range of bsulfonyl enamines without electron-withdrawing groups on the nitrogen atom. These enamines are found to be suitable for av ariety of further transformations.Alkynes are one of the most common and versatile functional groups in organic synthesis,and catalytic methods that enable their efficient transformation into other useful functionalities are therefore highly appealing in both academic research and industrial applications.[1] Direct difunctionalization reactions of alkynes,c apable of affording tri-and tetrasubstituted alkenes,h ave attracted much attention in recent years.[2] Among these,r adical-based 1,2-difunctionalizations of alkynes offer astraightforward means to construct functionalized alkenes by reaction with both carbon- [3] and heteroatom-centered radicals [4] with excellent step-and atomeconomy.[5] Mechanistically,ac ommon reaction pathway is observed involving initiation of the reaction by radical addition to the alkyne to generate av inyl radical intermediate,w hich is then coupled with another component to form the alkene product ( Figure 1a). However,s uch vinyl radical species are highly reactive and readily undergo hydrofunctionalization by H-atom abstraction, [6] which is as ignificant challenge in developing radical-based alkyne difunctionalization reactions.M oreover,a liphatic alkynes are generally unreactive in these processes,which is most likely due to the lack of a p-conjugation stabilizing effects of intermediate alkyl-substituted vinyl radicals compared to aryl-substituted analogues.[7] Consequently,c onceptually distinct approaches are in high demand. In the last years,t he nitrogenation of alkynes with trimethylsilylazide (TMSN 3 )has attracted much attention, where carbon-carbon triple bond cleavage leads to av ariety of nitrogen-containing molecules.[8] Building from our recent efforts on the activation of alkynes by silver catalysis, [9] we herein report an ew strategy to effect radicalbased difunctionalization of terminal alkynes through an unprecedented hydroazidation/ radical addition cascade (Figure 1b). Thek ey point for this successful transformation is that we discovered amild and efficient approach to generate sulfonyl radical from sodium sulfinate,t hus avoiding the initial competitive radical addition to alkynes.[6] To the best of our knowledge,t his is the first example of intermolecular alkyne aminosulfonylation, [10] resulting in stereoselective synthesis of b-sulfonyl N-unprotected enamines,w hich are useful synthetic intermediates whose applications are currently limited by al ack of practical synthetic methods for their preparation.[11] Moreover,only one report regarding the synthesis of N-unprotected enami...

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N-Trifluoromethylthiolated Sulfoximines

Cited by 79 publications

References 46 publications

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers

Oxidative Coupling with S–N Bond Formation

Silver‐Catalyzed Stereoselective Aminosulfonylation of Alkynes

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