88596-26-3Relevant academic research and scientific papers
Method for preparing aryl vinyl alkyl thioether through C/C-S monatomic assembly process
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Paragraph 0095; 0100-0101; 0106-0108, (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.
Efficient visible light initiated hydrothiolations of alkenes/alkynes over Ir2S3/ZnIn2S4: Role of Ir2S3
Li, Yuanyuan,Li, Zhaohui,Wang, Xinglin
, p. 409 - 416 (2020/07/30)
The hydrothiolations of alkynes/alkenes with thiols is an atom-economic and thus attractive method for the constructions of C-S bonds. Here Ir2S3/ZnIn2S4 nanocomposites with varied Ir2S3 loadings were obtained by one-pot solvothermal method from ZnCl2, InCl3 and thioacetamide with IrCl3. The loading of Ir2S3 on the surface of ZnIn2S4 promoted the hydrothiolations of alkenes and alkynes, with an optimum performance observed over 0.5 molpercent Ir2S3/ZnIn2S4 nanocomposite. Based on the studies on the performance of several other cocatalysts (MoS2, NiS and Pd) loaded ZnIn2S4 and the EIS analyses, it was proposed that the superior performance over Ir2S3/ZnIn2S4 nanocomposite can be ascribed to an improved efficiency on the photogeneration of the thiyl radicals by loading Ir2S3 as well as its inactivity for photocatalytic hydrogen evolution, a side reaction in the light initiated hydrothiolation reaction over ZnIn2S4. This study not only demonstrates an efficient and green strategy to synthesize thiolated products under visible light based on semiconductor photocatalysis, but also provides some guidances for the design and development of photocatalytic systems for light induced organic syntheses.
Synthesis of benzyl sulfidesviasubstitution reaction at the sulfur of phosphinic acid thioesters
Nishiyama, Yoshitake,Hosoya, Takamitsu,Yoshida, Suguru
supporting information, p. 5771 - 5774 (2020/06/03)
An ambident electrophilicity of phosphinic acid thioesters is disclosed. Unexpected carbon-sulfur bond formation took place in the reaction between phosphinic acid thioesters and benzyl Grignard reagents. The developed method for benzyl sulfides has a wide substrate scope and was applicable for the synthesis of a drug analog.
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.
Anti-Markovnikov stereoselective hydroamination and hydrothiolation of (hetero)aromatic alkynes using a metal-free cyclic trimeric phosphazene base
Zhao, Na,Lin, Chengdong,Wen, Lirong,Li, Zhibo
, p. 3432 - 3440 (2019/05/15)
Hydroamination and hydrothiolation are the most efficient and completely atom-economical process to construct important enamine and vinyl sulfide intermediates in pharmaceutical and organic chemistry. The cyclic trimeric phosphazene base (CTPB) showed gre
Visible light initiated hydrothiolation of alkenes and alkynes over ZnIn2S4
Li, Yuanyuan,Cai, Jingyu,Hao, Mingming,Li, Zhaohui
, p. 2345 - 2351 (2019/05/21)
The construction of C-S bonds is very important. The hydrothiolation of alkenes or alkynes with thiols represents an attractive and atom economical approach for the formation of C-S bonds. In this manuscript, flowerlike microspheres of ZnIn2S4 consisting of interweaving nanoflakes were prepared by a solvothermal method and were applied for the first time in the visible light initiated hydrothiolation of alkenes and alkynes. The reactions between a broad range of thiols and alkynes or alkenes over irradiated ZnIn2S4 afford the corresponding hydrothiolated products in moderate to excellent yields. The mechanism proposed based on the ESR results suggests that the holes generated over irradiated ZnIn2S4 are reductively quenched by the thiols to generate thiyl radicals, which are added to the alkynes/alkenes to generate alkene/alkyl radicals for the propagation of thiol-ene/thiol-yne coupling reactions. The use of solar light and a semiconductor-based photocatalyst to realize the thiol-ene and thiol-yne coupling reactions in a green solvent (methanol), with only stoichiometric thiols required and applicable to a broad substrate scope, makes this reaction protocol a green, sustainable and cost-effective strategy for the synthesis of thiolated products. This study also highlights the great potential of semiconductor-based photocatalysis for advanced organic syntheses.
Design of highly selective alkyne hydrothiolation RhI-NHC catalysts: Carbonyl-triggered nonoxidative mechanism
Palacios, Laura,Meheut, Yoann,Galiana-Cameo, María,Artigas, María José,DI Giuseppe, Andrea,Lahoz, Fernando J.,Polo, Victor,Castarlenas, Ricardo,Pérez-Torrente, Jesús J.,Oro, Luis A.
, p. 2198 - 2207 (2017/06/19)
New RhI-IPr (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-carbene) complexes bearing an N,O-pyridine-2-methanolato (N-O) bidentate ligand have been prepared. The carbonyl complex Rh(N-O)(IPr)(CO) efficiently catalyzes the hydrothiolation of
Regioselective hydrothiolation of terminal acetylene catalyzed by magnetite (Fe3O4) nanoparticles
Rocha, Manuela S. T.,Rafique, Jamal,Saba, Sumbal,Azeredo, Juliano B.,Back, Davi,Godoi, Marcelo,Braga, Antonio L.
supporting information, p. 291 - 298 (2017/02/10)
Herein, we report a new and solvent-free methodology for the preparation of vinyl thioethers from terminal alkynes and thiols, using magnetite (Fe3O4) nanoparticles as a recyclable catalyst. With this greener method, the desired viny
Sulfamic acid: An efficient and recyclable catalyst for the regioselective hydrothiolation of terminal alkenes and alkynes with thiols
Rosa, Clarissa Helena,Peixoto, Maura Luise B.,Rosa, Gilber Ricardo,Godoi, Benhur,Galetto, Fábio Zazyki,D'Oca, Marcelo Gon?alves Montes,Godoi, Marcelo
supporting information, p. 3777 - 3781 (2017/09/09)
Herein, we described a new method for the preparation of thioethers through hydrothiolation of alkenes and alkynes, using sulfamic acid as a reusable catalyst. Generally, this new methodology afforded the desired products in very good yields, under metal
Luminescent Iridium(III) Pyridinium-Derived N-Heterocyclic Carbene Complexes as Versatile Photoredox Catalysts
Lam, Tsz Lung,Lai, Jing,Annapureddy, Rajasekar Reddy,Xue, Minying,Yang, Chen,Guan, Yunzhi,Zhou, Pingjian,Chan, Sharon Lai-Fung
supporting information, p. 10835 - 10839 (2017/09/26)
The development of novel luminescent iridium(III) complexes with highly tunable emission energy and versatile applications is of particular importance. In this Communication, a series of luminescent iridium(III) complexes supported by chromophoric pyridinium-derived N-heterocyclic carbene (NHC) ligands that display tunable emission from 516 to 682 nm were prepared. These complexes can be used as photocatalysts in photooxidation and photoreduction reactions and could have potential applications in pH sensing.
