59014-89-0Relevant academic research and scientific papers
Application of Bulky NHC-Rhodium Complexes in Efficient S-Si and S-S Bond Forming Reactions
Bo?t, Ma?gorzata,?ak, Patrycja
supporting information, p. 17579 - 17585 (2021/11/18)
The efficient and straightforward syntheses of silylthioethers and disulfides are presented. The synthetic methodologies are based on new rhodium complexes containing bulky N-heterocyclic carbene (NHC) ligands that turned out to be efficient catalysts in thiol and thiol-silane coupling reactions. These green protocols, which use easily accessible reagents, allow obtaining compounds containing S-Si and S-S bonds in solvent-free conditions. Additionally, preliminary tests on coupling of mono- and octahydro-substituted spherosilicates with selected thiols have proved to be very promising and showed that these catalytic systems can be used for the synthesis of a novel class of functionalized silsesquioxane derivatives.
Photochemical metal-free aerobic oxidation of thiols to disulfides
Spiliopoulou, Nikoleta,Kokotos, Christoforos G.
supporting information, p. 546 - 551 (2021/01/28)
Thiol oxidation to disulfides is an area of great importance in organic synthesis, both for synthetic and biological purposes. Herein, we report a mild, inexpensive and green photochemical approach for the synthesis of both symmetrical and non-symmetrical disulfides, using metal-free and environmentally friendly conditions. Utilizing phenylglyoxylic acid as the photoinitiator, common household bulbs as the light source and a simple inorganic salt as the additive, a versatile oxidation of thiols leading to products in excellent yields is described. This journal is
Visible-light photocatalytic selective aerobic oxidation of thiols to disulfides on anatase TiO2
Xu, Hui,Shi, Ji-Long,Lyu, Shaoshuai,Lang, Xianjun
, p. 1468 - 1473 (2020/04/29)
This work presents the visible-light photocatalytic selective oxidation of thiols to disulfides with molecular oxygen (O2) on anatase TiO2. The high specific surface area of anatase TiO2 proved to be especially critical in
TEMPO visible light photocatalysis: The selective aerobic oxidation of thiols to disulfides
Xu, Hui,Zhang, Yu-Fei,Lang, Xianjun
supporting information, p. 1520 - 1524 (2019/12/09)
TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) is well-established in orangocatalysis that usually work in synergy with transition-metal catalysis or semiconductor photocatalysis. Here, TEMPO was turned into a visible light photocatalyst to conduct the selective aerobic oxidation of thiols into disulfides. With O2 as an oxidant, a mild and efficient protocol for the selective oxidation of thiols into disulfides including symmetrical and unsymmetrical ones with 5 molpercent of TEPMO as a photocatalyst was developed at room temperature under the irradiation of 460 nm blue LEDs. It was found that a complex formed between TEMPO and thiols underpinned the visible light activity and disulfides were obtained in very high isolated yields. This work suggests that TEMPO takes diverse roles in for photocatalytic selective oxidative transformations with O2 as the oxidant.
Extended Pummerer fragmentation mediated by carbon dioxide and cyanide
Liu, Jian,Kragh, Rasmus R.,Kamounah, Fadhil S.,Lee, Ji-Woong
, (2020/10/30)
Pummerer rearrangement reactions generate sulfur (II) oxidation state from sulfur (IV) starting materials in the presence of activating reagents. We found unprecedented transformation of vinyl sulfoxide; disulfide formation reactions mediated by atmospheric pressure of carbon dioxide in extended Pummerer rearrangement reactions. Only under CO2 atmosphere, we observed moderate to high yields of disulfide starting from sulfur (IV) starting materials. Investigations on the reaction mechanism revealed that the degradation of the starting materials and the products was significant in the absence of CO2. Further evidence for the suggested reaction mechanism was obtained by a cross-over experiment and a radical trapping reagent.
Unsymmetrical Disulfides Synthesis via Sulfenium Ion
Parida, Amarchand,Choudhuri, Khokan,Mal, Prasenjit
supporting information, p. 2579 - 2583 (2019/07/15)
An umpolung approach for the synthesis of unsymmetrical disulfides via sulfenium ion is reported. In situ generated electrophilic sulfenium ion from electron-rich thiols reacted with second thiols to yield unsymmetrical disulfides. Using an iodine catalyst and 4-dimethylaminopyridine (DMAP)/water as promoter, the target syntheses were achieved in one pot under aerobic condition.
Synthesis and nano-Pd catalyzed chemoselective oxidation of symmetrical and unsymmetrical sulfides
Li, Xing,Du, Jia,Zhang, Yongli,Chang, Honghong,Gao, Wenchao,Wei, Wenlong
, p. 3048 - 3055 (2019/03/21)
A highly chemoselective, efficient and nano-Pd catalyzed protocol for the rapid construction of sulfoxides and sulfones via the oxidation of symmetrical and unsymmetrical sulfides using H2O2 as an oxidant has been developed, respectively. The ready availability of starting materials, easy recovery and reutilization of the catalyst, wide substrate scope, and high yields make this protocol an attractive alternative. The process also involves the metal-free and microwave-promoted synthesis of symmetrical diarylsulfides, and FeCl3-mediated preparation of symmetrical diaryldisulfides through the reaction of arenediazonium tetrafluoroborates with Na2S·9H2O as a sulfur source. In addition, unsymmetrical sulfides were generated via the K2CO3-mediated reaction of arenediazonium tetrafluoroborates with symmetrical disulfides.
A novel dual-nano assisted synthesis of symmetrical disulfides from aryl/alkyl halides
Devi, Namita,Hazarika, Sukanya,Gogoi, Prasanta,Barman, Pranjit
supporting information, p. 1927 - 1938 (2018/07/21)
Here, we have reported a novel approach towards dual-nano assisted synthesis of disulfides from coupling of alkyl/aryl halides and sulfur nanoparticles. The indium oxide nanoparticles as catalyst expedite the conversion and sulfur nanoparticle notably enhances the miscibility, providing a faster, high yielding and cost-effective process in ethanol-water system. The method has synthetic advantages in terms of mild reaction framework, catalyst regeneration, and absence of any sulfide or polysulfide linkage as by-product leading to a column free synthesis. A variety of alkyl, aryl and heteroaryl symmetrical disulfides are obtained in good to excellent yields up to exceeding 98%.
Synthesis of 3-Sulfenylindoles from Indoles and Various Sulfenylation Agents through Aerobic Oxidative C-S Bond Coupling
Xu, Chaorong,Yi, Shanli,Li, Meichao,Hu, Xinquan,Sun, Nan,Jin, Liqun,Hu, Baoxiang,Shen, Zhenlu
, p. 1914 - 1920 (2018/08/28)
A novel aerobic catalytic oxidation system for the sulfenylation of indoles with a variety of sulfenylation agents through oxidative C-S bond coupling has been successfully developed. The reactions were performed with potassium iodide as the catalyst, sodium nitrite as the co-catalyst, and molecular oxygen as the terminal oxidant in the presence of acetic acid. Under the optimal reaction conditions, a number of indoles could be sulfenylated with Bunte salts, thiols, or disulfides to generate 3-sulfenylindoles in good yields. This protocol provided an efficient and environmentally benign strategy for the synthesis of 3-sulfenylindoles.
Solvent free, palladium catalyzed highly facile synthesis of diaryl disulfides from aryl thiols
Dutta, Pratip Kumar,Majumder, Arpi,Dutta, Sanjay,Dhar, Basab Bijayi,Munshi, Parthapratim,Sen, Subhabrata
supporting information, p. 527 - 530 (2017/01/16)
An efficient solvent free Pd(pCH2S)2dba catalyzed green-chemical strategy for the synthesis of diaryl disulfides from aryl thiols in moderate to excellent yield is reported. Variety of diaryl disulfides were synthesized. The catalyst
