Metal-Catalyzed Carbon−Sulfur Bond Formation

and, Teruyuki Kondo; Mitsudo, Take‐aki

doi:10.1021/cr9902749

Cited by 1,346 publications

(460 citation statements)

References 198 publications

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“…Upon charging (delithiation), the long-chain polysulfide re-forms. However, now the C-S bond is stable [58][59] in the polysulfide reduction and oxidation process, providing anchor points for sulfide grafting and immobilization. This novel chemistry process addresses the challenge of polysulfide dissolution and the shuttle effect, and eventually solves the polysulfide dissolution issue.…”

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confidence: 99%

Nucleophilic substitution between polysulfides and binders unexpectedly stabilizing lithium sulfur battery

et al. 2017

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Polysulfide shuttling has been the primary cause of failure in lithium-sulfur (Li-S) battery cycling. Here, we demonstrate an uncleophilic substitution reaction between polysulfides and binder functional groups can unexpectedly immobilizes the polysulfides. The substitution reaction is verified by UV-visible spectra and X-ray photoelectron spectra. The immobilization of polysulfide is in situ monitored by synchrotron based sulfur K-edge X-ray absorption spectra. The resulting electrodes exhibite initial capacity up to 20.4 mAh/cm 2 , corresponding to 1199.1 mAh/g based on a micron-sulfur mass loading of 17.0 mg/cm 2 . The micron size sulfur transformed into nano layer coating on the cathode binder during cycling.Directly usage of nano-size sulfur promotes higher capacity of 33.7 mAh/cm 2 , which is the highest areal capacity reported in Li-S battery. This enhance performance is due to the reduced shuttle effect by covalently binding of the polysulfide with the polymer binder.2

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confidence: 99%

Nucleophilic substitution between polysulfides and binders unexpectedly stabilizing lithium sulfur battery

et al. 2017

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“…Using this protocol, the arylsulfide 7a was synthesised (yield: 80%). The reaction of 6a with the thiolate anion, prepared by the action of t-BuOK on the N,N-diethylaminoethylthiol, in the presence of a catalytic amount of tetrakis(-triphenylphosphine)palladium in n-butanol (method D) was also found to be useful in the preparation of the sulfide 7a (66%) [36,37].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis of new 4-[2-(alkylamino)ethylthio]pyrrolo[1,2-a]quinoxaline and 5-[2-(alkylamino)ethylthio]pyrrolo[1,2-a]thieno[3,2-e]pyrazine derivatives, as potential bacterial multidrug resistance pump inhibitors

Vidaillac

Guillon²,

Moreau³

et al. 2007

Journal of Enzyme Inhibition and Medicinal Chemistry

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The synthesis of new 4-[2-(alkylamino)ethylthio]pyrrolo[1,2-a ]quinoxaline derivatives 1a-l is described in five or six steps starting from various substituted nitroanilines 2a-e. The bioisostere 5-[2-(alkylamino)ethylthio]pyrrolo[1,2-a ]thieno[3,2-e ]pyrazine 1m was also prepared. The new derivatives were evaluated as efflux pump inhibitors (EPIs) in a model targeting the NorA system of Staphylococcus aureus. The antibiotic susceptibility of two strains overproducing NorA, SA-1199B and SA-1, was determined alone and in combination with the neo-synthesised compounds by the agar diffusion method and MIC determination, in comparison with reserpine and omeprazole taken as reference EPIs. A preliminary structure-activity relationship study firstly allowed to clarify the influence of the substituents at positions 7 and/or 8 of the pyrrolo[1,2-a ]quinoxaline nucleus. Methoxy substituted compounds, 1b and 1g, were more potent EPIs than the unsubstituted compounds (1a and 1f), followed by chlorinated derivatives (1c-d and 1h). Moreover, the replacement of the N,N-diethylamino group (compounds 1a-e) by a bioisostere such as pyrrolidine (compounds 1f-h) enhanced the EPI activity, in contrast with the replacement by a piperidine moiety (compounds 1i-k). Finally, the pyrrolo[1,2-a ]thieno[3,2-e ]pyrazine compound 1m exhibited a higher EPI activity than its pyrrolo[1,2-a ]quinoxaline analogue 1a, opening the way to further pharmacomodulation.

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“…In particular, a thioether is a popular and useful compound [1][2][3][4][5]. Therefore, there are various types of synthetic methods to produce thioethers such as hydrothiolation of alkenes [6][7][8][9], Chan-Lam-Evans coupling using thiols [10], and transition metal-catalyzed coupling between aryl halides and thiols [11,12]. The substitution reaction of alkyl halides with sulfur nucleophiles is one of the most typical and practical methods in the synthesis of alkyl thioethers (Scheme 1A) [13][14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Thioethers by InI3-Catalyzed Substitution of Siloxy Group Using Thiosilanes

et al. 2016

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Abstract:The substitution of a siloxy group using thiosilanes smoothly occurred in the presence of InI 3 catalyst to yield the corresponding thioethers. InI 3 was a specifically effective catalyst in this reaction system, while other typical Lewis acids such as BF 3 ·OEt 2 , AlCl 3 , and TiCl 4 were ineffective. Various silyl ethers such as primary alkyl, secondary alkyl, tertiary alkyl, allylic, benzylic, and propargylic types were applicable. In addition, bulky OSitBuMe 2 and OSiiPr 3 groups, other than the OSiMe 3 group, were successfully substituted. The substitution reaction of enantiopure secondary benzylic silyl ether yielded the corresponding racemic thioether product, which suggested that the reaction of tertiary alkyl, secondary alkyl, benzylic, and propargylic silyl ethers would proceed via a S N 1 mechanism.

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Metal-Catalyzed Carbon−Sulfur Bond Formation

Cited by 1,346 publications

References 198 publications

Nucleophilic substitution between polysulfides and binders unexpectedly stabilizing lithium sulfur battery

Nucleophilic substitution between polysulfides and binders unexpectedly stabilizing lithium sulfur battery

Synthesis of new 4-[2-(alkylamino)ethylthio]pyrrolo[1,2-a]quinoxaline and 5-[2-(alkylamino)ethylthio]pyrrolo[1,2-a]thieno[3,2-e]pyrazine derivatives, as potential bacterial multidrug resistance pump inhibitors

Synthesis of Thioethers by InI3-Catalyzed Substitution of Siloxy Group Using Thiosilanes

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