- Iodine/Manganese Dual Catalysis for Oxidative Dehydrogenation Coupling of Amines with Thiols
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A novel dual catalytic system of iodine and manganese is used for the first time for oxidative dehydrogenation coupling of amines with thiols during aerobic oxidation. Sulfenamides are synthesized via this approach with moderate to high efficiencies. The mechanistic studies indicate that activated MnO2 is an electron transfer bridge for assisting iodine in completing the catalytic cycle.
- Liu, Shengping,Qi, Zaojuan,Qian, Bo,Zhang, Zhang
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supporting information
(2019/10/08)
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- Comparison of conventional and microwave-assisted synthesis of some new sulfenamides under free catalyst and ligand
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Abstract: Sulfenamide and its derivatives (S–N bond) have been synthesized with classical method in the literature. However, microwave-assisted synthesis of a series of N-(substituted phenylthio), N-(benzylthio), N-(cyclothio), and N-(2-mercaptobenzimidazolyl)amines has been not in the literature yet. They have been obtained from treating some amines (4?mmol) with thiophthalimides (PhthSR, 1?mmol) using sulfur transfer reagent in the presence of 2-ethoxyethanol (β-ee, neat) under microwave irradiation at 50?°C. The scope of this reaction was shown by the efficient synthesis of sulfenamides in good to excellent yields of 70–98% under free catalyst and ligand. Nine of the synthesized sulfenamide derivatives are novel. All of the thiols react with morpholine to give corresponding sulfenamides in excellent yields of 78–98%. Thiophenol, 4-methylthiophenol, 4-chlorothiophenol, and 4-fluorothiophenol react with cyclohexylamine to give corresponding sulfenamides in high yields 81–92%. Thiophenol, 4-methylthiophenol, 4-chlorothiophenol react with pyrrolidine to give corresponding sulfenamides in good yields of 70–76%. We observed that the reaction of t-butylamine with N-(phenylthio)phthalimide gave desired sulfenamide under microwave irradiation in the presence of DPPH as radical scavenger reagent in high yield of 93%. Aniline, benzylamine, 1-hexylamine, ethanolamine, diethylamine, N-ethyl-n-butylamine, N-ethylaniline, N-benzylmethylamine, t-butylamine react with thiols to give symmetrical disulfides instead of desired products under microwave irradiation, 2-ethoxyethanol as a solvent (neat), and at 50?°C. In this study, microwave-assisted synthesis method was compared with the classical method. All the products obtained were purified with chromatographic method and the analysis of these products was confirmed with IR, 1H NMR, 13C NMR spectroscopy, MS spectrometry, and elemental methods. Graphical abstract: [Figure not available: see fulltext.].
- Yakan, Hasan,Kütük, Halil
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p. 2047 - 2057
(2018/09/25)
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- Reaction of Thioaldehydes with Amines
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The reaction of phosphonium ylides with elemental sulfur gave thioaldehydes, which changed to the corresponding thioamides in good yields when treated with amines.When thioaldehydes containing α-hydrogens were treated with secondary amines, the corresponding enamines or reduction products were obtained.
- Okuma, Kentaro,Komiya, Yasuo,Ohta, Hiroshi
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p. 2402 - 2406
(2007/10/02)
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- Sulfenylation of Some Pyrroles and Indoles
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Methylsulfenylation of 1-substituted pyrroles and indoles was observed using 1-(methylthio)morpholine and an acid catalyst or with methylsulfenyl chloride and excess pyridine. 1-Substituents which are activating or weakly deactivating towards electrophili
- Gilow, Helmuth M.,Brown, Christopher S.,Copeland, John N.,Kelly, Keith E.
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p. 1025 - 1034
(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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