- PdCl2/DMSO-Catalyzed Thiol-Disulfide Exchange: Synthesis of Unsymmetrical Disulfide
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Unsymmetrical disulfides have been effectively prepared through thiol exchange with symmetrical disulfides employing a simple PdCl2/DMSO catalytic system. The given method features excellent functional group tolerance, a broad substrate scope, and operational simplicity. This reaction is especially useful for late-stage functionalization of bioactive scaffolds such as peptides and pharmaceuticals. Disulfide-containing organic dyes have also been prepared. This transformation could be extended to thiol-diselenide or thiol-ditelluride exchange affording RS-SeR′ or RS-TeR′.
- Guo, Jimin,Zha, Jianjian,Zhang, Tao,Ding, Chang-Hua,Tan, Qitao,Xu, Bin
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supporting information
p. 3167 - 3172
(2021/05/05)
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- Copper(I) iodide catalyzed 3-sulfenylation of indoles with unsymmetric benzothiazolyl-containing disulfides at room temperature
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A highly efficient protocol for the synthesis of 3-sulfenylindoles in moderate to excellent yields via the reaction of indoles with unsymmetric benzothiazolyl-containing disulfides is described. Copper(I) iodide is used as the catalyst and the reactions t
- Ge, Wenlei,Wei, Yunyang
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supporting information; experimental part
p. 934 - 940
(2012/04/23)
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- Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake
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Benzyl 4-halobenzyl and ally benzyl disulfide were synthesized as diallyl disulfide analogues and their tumor growth inhibitory effects on the cancer cells (SNU C5 and MCF-7) were comparable to that of diallyl disulfide, indicating that the disulfide func
- Ryu, Eun Kyoung,Choe, Yearn Seong,Byun, Sang Sung,Lee, Kyung-Han,Chi, Dae Yoon,Choi, Yong,Kim, Byung-Tae
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p. 859 - 864
(2007/10/03)
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- Disulfides. 1. Syntheses Using 2,2'-Dithiobis(benzothiazole)
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2,2'-Dithiobis(benzothiazole) produces unsymmetric disulfides containing the 2-benzothiazolyl fragment in both high yield and purity when reacted with 1 equiv of a variety of alkane and arene thiols under mild conditions.In turn, these unsymmetric disulfides react with a variety of thiols to produce either symmetric disulfides or new unsymmetric disulfides in excellent yields.At room temperature, 2 equiv of most thiols are oxidized essentially quantitatively to the corresponding symmetric disulfide by 2,2'-dithiobis(benzothiazole).Thiols employed at various stages include 1-propanethiol, 2-propanethiol, 2-methyl-2-propanethiol, phenylmethanethiol, 2-mercaptoethanol, 2-mercaptoethylamine (MEA) hydrochloride, 2-methoxybenzenethiol, 4-methoxybenzenethiol, 4-aminobenzenethiol, 4-acetamidobenzenethiol, 4-bromobenzenethiol, 4-methylbenzenethiol, N-acetyl-L-cysteine, and sodium 2-mercaptoethanesulfonate (MESNA).Various disulfides were inactive in vivo against cyanide poisoning.
- Brzezinska, Ewa,Ternay, Andrew L.
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p. 8239 - 8244
(2007/10/02)
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- N3-(ARYLTHIO-, ARALKYLTHIO- AND ALKYLTHIO)-5,5-DIMETHYLHYDANTOINS: SULFENYL GROUP TRANSFER REACTIONS AND THEIR PROPERTIES
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Sulfenyl-transfer reactions toward a variety of nucleophiles were successfully carried out using N3-sulfenyl-substituted 5,5-dimethylhydantoins (2a-c).During the course of the synthesis of 2 by the reaction of N1-bromo-5,5-dimethylhydantoin (1c) with disulfides, the sulfenyl groups were found to be at the position of N3 although the bromine was at N1 in the starting monobromohydantoin (1c).Some mechanistic speculations were considered for the formation of 2 from 1c.
- Takeda, Ken'ichi,Horiki, Kusuo
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p. 367 - 373
(2007/10/02)
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