- Scalable electrochemical oxidant-and metal-free dehydrogenative coupling of S-H/N-H
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A practical and scalable electrochemical oxidation of S-H and N-H was developed. This oxidant- and catalyst-free electrochemical process enables S-N bond formation with inexpensive nickel electrodes in an undivided cell. This procedure exhibits broad substrate scopes and good functional-group compatibility. A 50 g scale oxidative coupling augurs well for industrial applications.
- Tang, Shanyu,Liu, Yan,Li, Longjia,Ren, Xuanhe,Li, Jiao,Yang, Guanyu,Li, Heng,Yuan, Bingxin
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supporting information
p. 1370 - 1374
(2019/02/14)
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- Reusable cobalt-phthalocyanine in water: Efficient catalytic aerobic oxidative coupling of thiols to construct S-N/S-S bonds
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A new aerobic oxidative coupling of thiols in water to construct sulfenamides or disulfides was developed, utilizing cobalt(ii)phthalocyanine-tetra-sodium sulfonate as the catalyst and O2 as the oxidant. The mother liquor could be recycled up to 20 times with negligible loss of activity and only a minor decrease of product yield.
- Dou, Yingchao,Huang, Xin,Wang, Hao,Yang, Liting,Li, Heng,Yuan, Bingxin,Yang, Guanyu
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supporting information
p. 2491 - 2495
(2017/07/17)
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- Hypervalent iodine(III)-promoted metal-free S-H activation: An approach for the construction of S-S, S-N, and S-C bonds
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The activation of the sulfur atom of thiols with (diacetoxyiodo)benzene (DIB) has been explored in the preparation of symmetrical disulfides and sulfenamides. Disulfides can be produced in excellent yields (75-95%) upon treatment of thiols with DIB. The reaction was complete in less than five minutes at room temperature. Aliphatic, aromatic, and heteroaromatic thiols are compatible with this transformation. Moreover, heteroaromatic disulfides obtained from heteroaromatic thiols further reacted with a nucleophilic amine in the presence of a base to provide the corresponding sulfenamides in fair to good yields (43-90%) in a one-pot fashion. The methodology was successfully extended to indole as a representative electron-rich aromatic compound, which allowed successful construction of a S-C bond in one pot. The key benefits of this reaction include lower toxicity, low cost of DIB reagent, and mild reaction conditions (room temperature, undried solvents and open flask).
- Rattanangkool, Eakkaphon,Krailat, Watanya,Vilaivan, Tirayut,Phuwapraisirisan, Preecha,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
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p. 4795 - 4804
(2014/08/05)
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- Novel sulfenamides as promising acetylcholinesterase inhibitors
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Several sulfenamide derivatives were designed as possible acetylcholinesterase (AChE) inhibitors. New sulfenamides were synthesized and proved to be stable under the physiological conditions used in the enzymatic assays. N-benzyl-2-benzoxazolylsulfenamide (8) and N-benzyl-2- benzimidazolylsulfenamide (9) revealed anti-AChE activity with IC50 values of 0.6 and 0.8 μM, respectively, values of the same magnitude as those reported for galantamine and tacrine. The affinity for the biological site was evaluated in terms of interaction/partition toward sodium dodecyl sulfate (SDS) micelles. The inhibitory activity profiles were reasoned in terms of both partition toward a hydrophobic anionic environment and molecular geometry. The X-CSN dihedral angle deviations from collinearity stood out as a major parameter linked to enzyme specificity. Copyright
- Proenca, Carla,Serralheiro, M. Luisa,Araujo, M. Eduarda,Pamplona, Teresa,Santos, Susana,Santos, M. Soledade,Frazao, Fatima
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experimental part
p. 1287 - 1294
(2012/01/12)
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- Electronic Structure and Spectra of Some Benzothiazole-2-Sulfenamide Derivatives
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The electronic structures and spectra of N,N-diethanol-, N-oxadiethylene- and N-benzylbenzothiazole 2-sulfenamide derivatives have been examined both theoretically and experimentally. Equilibrium geometries were determined employing a full geometry optimization using AMI-MO method. The calculated geometric parameters were analyzed in terms of total energy, heat of formation, ionization potential, dipole moments, net charge, bond lengths and bond angles. The electronic absorption spectra were measured in the UV region. The observed spectra consisted of broad envelopes, expectedly composed of overlapping bands. Therefore, Gaussian analysis and MO computations of the spectra were performed as quantitative interpretation of the observed spectra. Analysis of the computed CI states and the MO's involved enabled the assignment of the observed bands. Their origin was assumed as being due to delocalized, localized, or charge transfer transitions. Solvent effects on band position and intensities have also been investigated.
- Moustafa, H.,Abdou, N. Y.,Hamed, M. M.
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p. 309 - 326
(2007/10/03)
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- Process for the preparation of thiazolesulphenamides
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Thiazolesulphenamides, useful as rubber vulcanization accelerators, are made by reaction of a 2-mercapto-thiazole or a 2,2'-dithiazolyl disulphide with ammonia or a primary or secondary amine in the presence of oxygen and a copper catalyst of specified kind.
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