7214-53-1Relevant articles and documents
Method for preparing aryl vinyl alkyl thioether through C/C-S monatomic assembly process
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Paragraph 0095; 0100-0101; 0109-0111, (2022/04/08)
The invention discloses a method for preparing aryl vinyl alkyl thioether through a C = C-S monatomic assembly process, which comprises the following steps: respectively providing an atom for a C = C-S structure by dimethyl sulfoxide, aromatic aldehyde ketone and sulfur-containing reagent sodium mercaptide/dithioether under the action of air atmosphere and alkali; the construction process is completed by one-pot reaction, and the product aryl vinyl alkyl thioether compound is obtained. The aryl vinyl of the aryl vinyl alkyl thioether compound prepared by the method comes from aromatic aldehyde ketone, but a double-bond carbon atom is added compared with the original aromatic aldehyde ketone raw material, and the method has the advantages of wide and easily available raw material source, environmental protection, low price, simple operation and facilitation of industrial production.
Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
Harenberg, Johannes H.,Weidmann, Niels,Karaghiosoff, Konstantin,Knochel, Paul
supporting information, p. 731 - 735 (2020/11/30)
The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set-up using NaDA (sodium diisopropylamide) in EtNMe2 or NaTMP (sodium 2,2,6,6-tetramethylpiperidide)?TMEDA in n-hexane provides sodiated acrylonitriles and alkenyl sulfides, which are subsequently trapped in batch with various electrophiles such as aldehydes, ketones, disulfides and allylic bromides affording functionalized acrylonitriles and alkenyl sulfides. This flow-procedure was successfully extended to other acrylates by using Barbier-type conditions.
Sulfur?oxygen interaction-controlled (Z)-selectiveanti-Markovnikov vinyl sulfides
Pramanik, Milan,Mathuri, Ashis,Mal, Prasenjit
supporting information, p. 5698 - 5701 (2021/06/16)
The sulfur oxygen (S?O) interaction was used herein to obtain (Z)-selectiveanti-Markovnikov vinyl sulfides from the addition of thiyl radicals to terminal alkynes. DFT calculations predicted that S?O interaction originated from the delocalization of the lone-pair of the carbonyl oxygen to the adjacent σ* orbital of the S atom of C-S.
Catalytic conversion of alkynes to α-vinyl sulfides mediated by carbene-linker-carbene (CXC) rhodium and iridium complexes
Tolley, Lewis C.,Fernández, Israel,Bezuidenhout, Daniela I.,Guisado-Barrios, Gregorio
, p. 516 - 523 (2021/02/09)
The catalytic activity of a set of mono- and bimetallic Rh(i) and Ir(i) complexes bearing carbene-linker-carbene (CXC) bis-triazolylidene ligands (with X = O, N) coordinated in a bridging or chelating fashion was evaluated in the hydrothiolation of alkyne
Pd-Catalyzed Double-Decarbonylative Aryl Sulfide Synthesis through Aryl Exchange between Amides and Thioesters
Bie, Fusheng,Cao, Han,Liu, Chengwei,Liu, Xuejing,Shi, Yijun,Szostak, Michal,Zhou, Tongliang
, p. 8098 - 8103 (2021/10/25)
We report the palladium-catalyzed double-decarbonylative synthesis of aryl thioethers by an aryl exchange reaction between amides and thioesters. In this method, amides serve as aryl donors and thioesters are sulfide donors, enabling the synthesis of valuable aryl sulfides. The use of Pd/Xantphos without any additives has been identified as the catalytic system promoting the aryl exchange by C(O)-N/C(O)-S cleavages. The method is amenable to a wide variety of amides and sulfides.
Novel reaction course of thiiranes to vinyloxiranes: Reaction of benzyne with thiiranes and aldehydes
Okuma, Kentaro,Qu, Yuxuan,Nagahora, Noriyoshi
, p. 1294 - 1300 (2021/07/19)
Reaction of 2 molar amount of 2-(trimethylsilyl)phenyl triflate with thiiranes and aldehydes in the presence of CsF afforded vinyloxiranes in one-pot operation. Reaction of benzyne with thiiranes gave the corresponding alkenyl phenyl sulfides, which furth
Selectivity control in thiol-yne click reactions: Via visible light induced associative electron upconversion
Ananikov, Valentine P.,Burykina, Julia V.,Gordeev, Evgeniy G.,K?nig, Burkhard,Shlapakov, Nikita S.
, p. 10061 - 10070 (2020/10/13)
An associative electron upconversion is proposed as a key step determining the selectivity of thiol-yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range of products-four types of vinyl sulfides were prepared in high yields and selectivity. We report practically important transition-metal-free regioselective thiol-yne addition and formation of the demanding Markovnikov-type product by a radical photoredox process. The photochemical process was directly monitored by mass-spectrometry in a specially designed ESI-MS device with green laser excitation in the spray chamber. The proposed reaction mechanism is supported by experiments and DFT calculations. This journal is
Facile Thiol–Ene Click Protocol Using Benzil as Sensitizer and White LED as Light Source
Das, Anupam,Thomas, K. R. Justin
supporting information, p. 7214 - 7218 (2020/11/30)
The thiol–ene reaction leading to a series of thioether derivatives by simple metal and oxidant free visible light promoted photosensitized protocol, following anti-Markonikov hydrothiolation of unactivated aryl and alkyl olefins at room temperature is demonstrated. Benzil served as a green photosensitizer in this reaction and white LED lights as a light source. This radical based thiol–ene reaction is operationally simple and tolerates a wide variety of functional groups present in olefins.
Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions
Castoldi, Laura,Di Tommaso, Ester Maria,Gr?fen, Barbara,Olofsson, Berit,Reitti, Marcus
supporting information, p. 15512 - 15516 (2020/06/23)
The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.
A Simplified Protocol for the Stereospecific Nickel-Catalyzed C-S Vinylation Using NiX 2 Salts and Alkyl Phosphites
Larin, Egor M.,Lautens, Mark,Marchese, Austin D.,Mirabi, Bijan
, p. 311 - 319 (2019/12/28)
A Ni-catalyzed C-S cross-coupling using only NiI 2 (0.5-2.5 molpercent) and P(O i Pr) 3 (2.0-10.0 molpercent) is reported. Using an air-stable Ni(II) precatalyst, and a cheap and commercially available ligand, a scalable and robust method was developed to cross-couple various thiophenols and styryl bromides, including some sterically encumbered thiols, an α-bromocinnamaldehyde as well as a thiolation-cyclization.
