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Catalysis with Selenium and Sulfur
Published in Andrew M. Harned, Nonnitrogenous Organocatalysis, 2017
Some recent efforts exploited the Lewis basic nature of triphenylphosphine sulfide (144) and used it as a catalyst in halogenation reactions. Gustafson and coworkers reported an electrophilic halogenation of heterocycles and simple arenes such as 145, using N-halosuccinimides as the halogen source (Scheme 5.35).82 The study was centered on the more challenging chlorination reaction, owing to the relative inertness of NCS as compared to the bromine and iodine counterparts. It was also found that the yield was significantly eroded when the S on the catalyst was replaced with other chalcogens such as O and Se. Preceding this report, triphenylphosphine sulfide (144) has been used by Denmark and coworker as a Lewis base catalyst of halocyclization reactions.32
A new cuprous coordinating polymer constructed by bridging 2,2-(1,4-butanediyl)bis-1,3-benzoxazole ligand: synthesis, structure, and properties
Published in Journal of Coordination Chemistry, 2019
Cong Wang, Yao Qu, Yancong Wu, Kesheng Shen, Kun Zhao, Chuang Li, Guozhen Huang, Xintong Han, Huilu Wu
Benzoxazole is a heterocyclic compound containing nitrogen and oxygen atoms having a non-centrosymmetric structure, and introducing substituents of different functions and structures on the oxazole ring to form benzoxazole derivatives having different structures and functions [14, 15]. Benzoxazole and its derivatives have a wide range of biological activities and good optical properties, and are widely used in various fields such as chemical engineering, aerospace, optoelectronic materials, life sciences, and medicine [16]. At the same time, benzoxazole and its derivatives have strong coordination ability and diverse coordination configurations [17]. Triphenylphosphine sulfide as a sulfur-containing ligand not only has a large steric hindrance to reduce the structural deformation of the copper(I) complexes, but also the unique electronic effect of the sulfur atom stabilizing the copper(I). Some cuprous complexes with benzoxazole or triphenylphosphine sulfide such as discrete monomers, dimeric clusters and CPs have been reported by several research groups [18–22]. The electronic and structural characteristics of the benzoxazole ligands play an important role in determining the overall structure of the copper(I) complexes and consequently their photophysical properties [23–25].
Synthesis, crystal structure, fluorescence and electrochemical properties of two Ag(I) complexes based on 2-(4′-pyridyl)-benzoxazole/SPPh3 ligands
Published in Journal of Coordination Chemistry, 2018
Shanshan Mao, Xintong Han, Chuang Li, Guozhen Huang, Kesheng Shen, Xinkui Shi, Huilu Wu
AgNO3, [Ag(CH3CN)4ClO4] were obtained from Sigma-Aldrich Co. (USA). The solvents were produced at Tianjin Kaitong Chemical Reagent Co., Ltd. (China). All chemicals and solvents were reagent grade and used without purification. C, H, and N elemental analyses were performed using a Carlo Erba 1106 elemental analyzer. IR spectra were recorded from 4000 to 400 cm−1 with a Nicolet FT-VERTEX 70 spectrometer using KBr pellets. Electronic spectra were taken on a Lab-Tech UV Bluestar spectrophotometer. Absorbance was measured with the Spectrumlab722sp spectrophotometer at room temperature. Electrochemical measurements were performed on a LK2005A electrochemical analyzer under nitrogen at 283 K. A glassy carbon working electrode, a platinum-wire auxiliary electrode and an Ag/AgCl reference electrode ([Cl−1] = 1.0 mol L−1) were used in the three-electrode measurements. The electroactive component was at 1.0 × 10−3 mol·dm−3 concentration with tetrabutylammonium perchlorate (TBAP) (0.1 mol·dm−3) used as the supporting electrolyte in DMF. The fluorescence spectra were obtained with an F97 Pro fluorescence spectra fluorophotometer. 2-(4′-pyridyl)-benzoxazole (4-PBO) and triphenylphosphine sulfide (SPPh3) were synthesized according to reported methods [40, 41].
The behavior of some Wittig reagents toward 4,5,6,7-tetrahydro-3H-1,2-benzo[1,2]dithiole-3-thione
Published in Journal of Sulfur Chemistry, 2019
Ewies F. Ewies, Naglaa F. El-Sayed, Leila S. Boulos
A mixture of 1 (1 mmol, 0.19 g) and 2a-e (1 mmol) or 2f,g (2 mmol) was refluxed 2–10 h in 30 ml dry toluene. When the reaction was completed, the volatile materials were evaporated under reduced pressure. The residue was subjected to silica gel column chromatography to give products 5-7. Triphenylphosphine sulfide (TPPS) is also isolated and identified (m.p. and mix m.p.).