85169-05-7Relevant articles and documents
Transition Metal-Free C-H Thiolation via Sulfonium Salts Using β-Sulfinylesters as the Sulfur Source
Chen, Yanhui,Wen, Si,Tian, Qingyu,Zhang, Yuqing,Cheng, Guolin
supporting information, p. 7905 - 7909 (2021/10/20)
We disclose a direct C(sp)-, C(sp2)-, and C(sp3)-H thiolation reaction using β-sulfinylesters as the versatile sulfur source. The key step of this protocol is chemoselective C-S bond cleavage of the sulfonium salts that are formed in situ from the corresponding alkenes, alkynes, and 1,3-dicarboxyl compounds with β-sulfinylesters. The successful capture of the acrylate byproduct supports a retro-Michael reaction mechanism.
CuI-catalyzed tandem synthesis of thioethers using aryl halides, electron-deficient alkenes, and sodium iso-propyl xanthogenate
Abbasi, Mohammad,Nowrouzi, Najmeh,Khezri, Rahimeh
, (2020/02/11)
A ligand-free, CuI-catalyzed protocol was developed for the one-step preparation of Michael adducts of aromatic thiols in high yields by reacting a mixture of an aryl halide and an electron-deficient alkene with sodium iso-propyl xanthogenate.
One-pot odorless thia-Michael reaction by copper ferrite nanoparticle-catalyzed reaction of elemental sulfur, aryl halides and electron-deficient alkenes
Gholinejad, Mohammad,Firouzabadi, Habib
, p. 5953 - 5959 (2015/08/06)
In this article we report a non-odorous protocol for the high yield formation of aryl-alkyl sulfides by the reaction of aryl iodides, bromides and boronic acids with elemental sulfur and electron-deficient alkenes, catalyzed by copper ferrite nanoparticles. The catalyst was easily separated using an external magnetic bar and recycled for subsequent runs, its catalytic activity being preserved.
Crown ether complex cation ionic liquids: Preparation and applications in organic reactions
Song, Yingying,Jing, Huanwang,Li, Bo,Bai, Dongsheng
experimental part, p. 8731 - 8738 (2011/09/16)
A series of crown ether complex cation ionic liquids (CECILs) were designed, synthesised and characterised by NMR spectroscopy, HRMS, thermogravimetric differential thermal analysis (TG-DTA) and elemental analysis. Their applications in various organic reactions were investigated: [15-C-5Na][OH], [15-C-5Na][OAc], [18-C-6K][OH] and [18-C-6K][OAc] (15-C-5=[15]crown-5; 18-C-6=[18]crown-6) efficiently catalysed the Michael addition of alkenes and relevant nucleophiles; [18-C-6K][OH] and [15-C-5Na][OH] effectively catalysed the Henry reaction of nitromethane and aromatic aldehydes; [18-C-6K][OH] has excellent catalytic efficiency for Knoevenagel condensation of aromatic aldehydes and malononitrile; PdCl2/[18-C-6K] 3[PO4]/K2CO3 efficaciously catalysed the Heck reaction of olefins and aromatic halides; [18-C-6K][BrO3] can be used as both oxidant and solvent in the oxidation reaction of aromatic alcohols. The CECIL catalysts [15-C-5Na][OH] (Michael addition) and [18-C-6K][OH] (Henry reaction) can be recycled and reused several times without obvious loss of activity and their recovery is very simple.
Organocatalytic asymmetric synthesis of sulfoxides from sulfenic acid anions mediated by a cinchona -derived phase-transfer reagent
Gelat, Fabien,Jayashankaran, Jayadevan,Lohier, Jean-Francois,Gaumont, Annie-Claude,Perrio, Stephane
supporting information; experimental part, p. 3170 - 3173 (2011/08/06)
Preliminary results concerning a conceptually novel route to chiral sulfoxides based on the asymmetric alkylation of sulfenate salts with alkyl halides mediated by a chiral phase-transfer catalyst are described. As a representative example, o-anisyl methyl sulfoxide was produced in 96% yield and with an enantiomeric excess of 58% using commercial cinchonidinium derivative 2a.
Reduction cleavage of S-S bond by Zn/Cp2tiCl2: Application for the synthesis of β-arylthiocarbonyl compounds
Xu, Xiao Bo,Yin, Xian Hong,Zhu, Yu Yang,Xu, Xin Hua,Luo, Tao,Li, Yin Hui,Lu, Xiong,Shao, Ling Ling,Pan, Jian Gao,Yang, Rong Hua
experimental part, p. 750 - 752 (2010/03/24)
Diaryl disulfides were reduced efficiently by a Zn/Cp2TiCl 2 system at room temperature in dry THF to give the corresponding nucleophilic sulfur anion-titanocene complex, followed by reaction with α, β-unsaturated esters (ketones or nitriles) to afford the corresponding β-arylthioesters(ketone or nitrile) in good yields.
Remarkably mild and simple preparation of sulfenate anions from β-sulfinylesters: A new route to enantioenriched sulfoxides
Caupene, Caroline,Boudou, Cedric,Perrio, Stephane,Metzner, Patrick
, p. 2812 - 2815 (2007/10/03)
(Chemical Equation Presented) A general, efficient, and experimentally simple method for the generation of sulfenate salts has been developed using β-sulfmylesters as substrates. The process is based on a retro-Michael reaction, initiated by deprotonation at low temperature. Upon treatment with alkyl halides, the liberated sulfenates are subsequently converted into sulfoxides in good to excellent yield. Extension of the methodology to an unprecedented access to nonracemic sulfoxides by introduction of an enantiopure ligand, (-)-sparteine, is also described.
A novel synthesis of β-arylthio propanoic esters promoted by low- valent titanium
Shi, Daqing,Lu, Zaisheng,Mu, Lailong,Dai, Guiyuan
, p. 1073 - 1078 (2007/10/03)
Promoted by low-valent titanium, aryl sulfonyl chlorides react with α,β-unsaturated esters in THF to give β-arylthio propanoic esters in moderate to good yields.
SYNTHESIS AND SPECTRAL STUDIES OF SOME NOVEL ETHYL (SUBSTITUTED PHENYLTHIO) ACETATE AND PROPIONATE DERIVATIVES
Hamed, Ezzat E.,El-Bardan, A. A.,Moussa, Adel M.
, p. 269 - 274 (2007/10/02)
Ethyl (substituted phenylthio) acetate and propionate derivatives have been synthesised, their structures were proved by IR, NMR and mass spectra.Key words: Arylthioacetates; arylthiopropionates; NMR- and mass spectra
