35390-53-5Relevant academic research and scientific papers
Iodine/Manganese Dual Catalysis for Oxidative Dehydrogenation Coupling of Amines with Thiols
Liu, Shengping,Qi, Zaojuan,Qian, Bo,Zhang, Zhang
supporting information, (2019/10/08)
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.
Comparison of conventional and microwave-assisted synthesis of some new sulfenamides under free catalyst and ligand
Yakan, Hasan,Kütük, Halil
, p. 2047 - 2057 (2018/09/25)
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.].
Unsymmetrical disulfide and sulfenamide synthesis via reactions of thiosulfonates with thiols or amines
Taniguchi, Nobukazu
, p. 2030 - 2035 (2017/03/17)
The reactivity of thiosulfonates with nucleophilic reagents was investigated. When reactions of thiosulfonates with thiols were performed, unsymmetrical disulfides were obtained in excellent yields. This procedure could employ numerous aryl or alkyl thiols. On the other hand, reactions of thiosulfonates with amines proceeded in the presence of a copper catalyst. The procedure was performed efficiently in air, and afforded the corresponding sulfenamides.
REACTION OF ARENESULFINIMIDIC ACID DERIVATIVES WITH THIOPHENOLS
Pel'kis, N. P.,Levchenko, E. S.
, p. 341 - 345 (2007/10/02)
The amides and esters of N-substituted arenesulfinimidic acids are reduced by the action of thiophenols primarily to N-substituted arenesulfenamides, while the thiophenols are oxidized to the corresponding derivatives of the arenesulfinic acids.
