59090-57-2Relevant articles and documents
Aryl thioether compound and preparation method thereof
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Paragraph 0012, (2021/11/27)
The invention discloses an aryl thioether compound and a synthesis method thereof, wherein an aryl carboxylic acid and a mercaptan (phenol) are used as main raw materials, and a nickel catalyst is prepared. Under the action of the phosphine ligand and the additive, the aryl carboxylic acid and the thiol (phenol) react in an organic solvent, and after the reaction is finished, the corresponding aryl thioether is obtained. The method has the advantages of low cost, high yield, simple and convenient operation, no pollution and the like, and has potential industrial application prospects. The method provides a cheap and green way for preparation of aryl thioether compounds.
Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
Lam, Long Yin,Ma, Cong
supporting information, p. 6164 - 6168 (2021/08/16)
A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.
DABCO-promoted Diaryl Thioether Formation by Metal-catalyzed Coupling of Sodium Sulfinates and Aryl Iodides
Liu, Yanpeng,Lam, Long Yin,Ye, Jiqing,Blanchard, Nicolas,Ma, Cong
supporting information, p. 2326 - 2331 (2020/05/05)
A scalable catalytic synthesis method using commodity chemicals for constructing diaryl thioethers directly from sodium arylsulfinates and iodoarenes is reported in this study. In the presence of CuO or other copper salts such as Cu(OAc)2 as well as palladium catalysts, DABCO demonstrated to be essential to promote this transformation. Various iodoarenes and aryl sulfinates were examined and demonstrated the viability of this method. The mechanistic study showed that radical reactions occurred, while DABCO N-oxide radical can be observed by mass spectrometry. A plausible catalytic mechanism involving DABCO is also discussed, suggesting synergistic reduction of sulfinate by Cu(II) and DABCO is the key step of this coupling reaction. (Figure presented.).
Cu-Mediated arylselenylation of aryl halides with trifluoromethyl aryl selenonium ylides
Wu, Shuai,Shi, Jin,Zhang, Cheng-Pan
supporting information, p. 7468 - 7473 (2019/08/20)
An unprecedented arylselenylation of aryl halides with trifluoromethyl aryl selenonium ylides in the presence of copper is described. The reaction proceeded at 100-140 °C under ligand- and additive-free conditions for 3-20 h to form a variety of unsymmetrical diaryl selenides in good to high yields. Arylselenylation is easy to operate, has good functional group tolerance, and demonstrates the different reaction profiles of trifluoromethyl aryl selenonium ylides from the homologous trifluoromethyl aryl sulfonium ylides.
Controlled Ni-catalyzed mono- and double-decarbonylations of α-ketothioesters
Zheng, Zhao-Jing,Jiang, Cheng,Shao, Peng-Cheng,Liu, Wen-Fei,Zhao, Tian-Tian,Xu, Peng-Fei,Wei, Hao
supporting information, p. 1907 - 1910 (2019/05/02)
A method for Ni-catalyzed controlled decarbonylation of α-ketothioesters is described. Mono- and double-decarbonylations, which gave thioesters and thioethers, respectively, were selectively achieved by changing the ligand. A fundamental study of Ni-catalyzed decarbonylation of α-ketothioesters is presented.
Triphenylsulfonium topophotochemistry
Despagnet-Ayoub,Kramer,Sattler,Sattler,Labeaume,Thackeray,Cameron,Cardolaccia,Rachford,Winkler,Gray
, p. 27 - 34 (2018/02/06)
The products from the 193 nm irradiation of triphenylsulfonium nonaflate (TPS) embedded in a poly(methyl methacrylate) (PMMA) film have been characterized. The analysis of the photoproduct formation was performed using chromatographic techniques including HPLC, GPC and GC-MS as well as UV-vis and NMR spectroscopic methods. Two previously unreported TPS photoproducts, triphenylene and dibenzothiophene, were detected; additionally, GPC and DOSY-NMR spectroscopic analyses after irradiation suggested that TPS fragments had been incorporated into the polymer film. The irradiation of acetonitrile solutions containing 10% w/v PMMA and 1% w/v TPS in a 1 cm-path-length cuvette showed only a trace amount of triphenylene or dibenzothiophene, indicating that topochemical factors were important for the formation of these molecules. The accumulated evidence indicates that both products were formed by in-cage, secondary photochemical reactions: 2-(phenylthio)biphenyl to triphenylene, and diphenylsulfide to dibenzothiophene.
Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts
Liu, Chengwei,Szostak, Michal
, p. 2130 - 2133 (2018/03/06)
A general, highly selective method for decarbonylative thioetherification of aryl thioesters by C-S cleavage is reported. These reactions are promoted by a commercially-available, user-friendly, inexpensive, air- and moisture-stable nickel precatalyst. The process occurs with broad functional group tolerance, including free anilines, cyanides, ketones, halides and aryl esters, to efficiently generate thioethers using ubiquitous carboxylic acids as ultimate cross-coupling precursors (cf. conventional aryl halides or pseudohalides). Selectivity studies and site-selective orthogonal cross-coupling/thioetherification are described. This thioester activation/coupling has been highlighted in the expedient synthesis of biorelevant drug analogue. In light of the synthetic utility of thioethers and Ni(ii) precatalysts, we anticipate that this user-friendly method will be of broad interest.
Room-Temperature Arylation of Thiols: Breakthrough with Aryl Chlorides
Jiang, Min,Li, Haifang,Yang, Haijun,Fu, Hua
supporting information, p. 874 - 879 (2017/01/14)
The formation of aryl C?S bonds is an important chemical transformation because aryl sulfides are valuable building blocks for the synthesis of biologically and pharmaceutically active molecules and organic materials. Aryl sulfides have traditionally been synthesized through the transition-metal-catalyzed cross-coupling of aryl halides with thiols. However, the aryl halides used are usually bromides and iodides; readily available, low-cost aryl chlorides often not reactive enough. Furthermore, the deactivation of transition-metal catalysts by thiols has forced chemists to use high catalyst loadings, specially designed ligands, high temperatures, and/or strong bases, thus leading to high costs and the incompatibility of some functional groups. Herein, we describe a simple and efficient visible-light photoredox arylation of thiols with aryl halides at room temperature. More importantly, various aryl chlorides are also effective arylation reagents under the present conditions.
ONIUM BORATE SALT, ACID GENERATOR, CURABLE RESIN COMPOSITION AND CURED BODY PREPARED THEREWITH
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Paragraph 0128, (2018/06/12)
PROBLEM TO BE SOLVED: To provide an onium borate salt and the like having cationic polymerizing performance and crosslinking reacting performance. SOLUTION: An onium borate salt contains onium borate salt (OB1) represented by general formula (1) and onium borate salt (OB2) represented by general formula (2), where the content of (OB2) in (OB1) and (OB2) is 0.01-4 wt.% [(R1)n+1-E]+ [(R2)bB(Ar)4-b]- (1), [(R1)n+1-E]+ [(OH)(R2)bB(Ar)3-b]- (2) [in formulae (1) and (2), E represents an n-valence element of Group VIA to Group VIIA (CAS notation) and n is an integer of 1 or 2; R1 is an organic group bonded to E; R2 is an organic group bonded to B (boron) and b is an integer of 1 to 3; and Ar represents a substituted phenyl group and b is an integer of 1 to 3]. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
A highly efficient heterogeneous copper-catalyzed Chan-Lam coupling between thiols and arylboronic acids leading to diaryl sulfides under mild conditions
Lin, Yang,Cai, Mingzhong,Fang, Zhiqiang,Zhao, Hong
, p. 3335 - 3343 (2016/05/19)
The heterogeneous Chan-Lam coupling reaction between thiols and arylboronic acids was achieved in EtOH at room temperature in the presence of 5 mol % of MCM-41-immobilized 1,10-phenanthroline-copper(II) complex [MCM-41-1,10-Phen-CuSO4] with n-Bu4NOH (40% aq) as base under O2 atmosphere, yielding a variety of unsymmetrical diaryl sulfides in good to excellent yields under mild and green conditions. The new heterogeneous copper complex can easily be prepared by a simple procedure from commercially readily available and inexpensive reagents, and recovered by a simple filtration of the reaction solution and recycled for at least eight times without significant loss of catalytic activity.
