7214-56-4

Upstream product

• 17101-71-2 Z-β-bromovinyl phenyl sulfide 
• 100-58-3 phenylmagnesium bromide 
• 97-93-8 triethylaluminum 
• 78839-92-6 2-phenyl-1-(phenylthio)ethenyl diphenyl phosphate 
• 121410-97-7 O-<2,2-bis(phenylthio)-1-phenylethyl> S-methyl dithiocarbonate 
• 95391-86-9 (Z)-(phenylthio)ethenyl methyl selenide 
• 75924-66-2 C₁₄H₁₂HgS 
• 588-73-8 (Z)-β-bromostyrene 
• 108-98-5 thiophenol 
• 40110-65-4 (+/-)_S-(Z)-2-phenyl-1-(phenylsulfinyl)ethene 
• 13884-92-9 phenylthiomethyl triphenylphosphonium chloride 
• 100-52-7 benzaldehyde 
• 536-74-3 phenylacetylene 
• 16212-06-9 phenyl styryl sulfone 

Downstream Products

• 873-66-5 1-propenylbenzene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 7214-53-1 (E)-[2-(phenylsulfanyl)vinyl]benzene 
• 134996-34-2 (Z)-3-phenyl-2-(phenylmercapto)-2-propenyl alcohol 
• 32291-77-3 phenyl (Z)-β-styryl sulphone 
• 98496-59-4 1-((Z)-2-Benzenesulfonyl-1-phenyl-ethenesulfonyl)-4-bromo-benzene 
• 98496-58-3 1-((Z)-2-Benzenesulfonyl-1-phenyl-ethenesulfonyl)-4-chloro-benzene 
• 98496-57-2 1-((Z)-2-Benzenesulfonyl-1-phenyl-ethenesulfonyl)-4-methyl-benzene 
• 98496-56-1 (Z)-α,β-bis(phenylsulfonyl)styrene 
• 98496-55-0 2-((Z)-2-Benzenesulfonyl-1-phenyl-vinylsulfanyl)-phenylamine 
• 98496-49-2 1-((Z)-2-Benzenesulfonyl-1-phenyl-vinylsulfanyl)-4-bromo-benzene 
• 98496-48-1 1-((Z)-2-Benzenesulfonyl-1-phenyl-vinylsulfanyl)-4-chloro-benzene 

Relevant academic research and scientific papers

Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates

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

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

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

Selectivity control in thiol-yne click reactions: Via visible light induced associative electron upconversion

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

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.

A Simplified Protocol for the Stereospecific Nickel-Catalyzed C-S Vinylation Using NiX 2 Salts and Alkyl Phosphites

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.

Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions

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.

Acetylene and terminal alkyne complexes of copper(i) supported by fluorinated pyrazolates: Syntheses, structures, and transformations

Trinuclear {μ-[3,5-(CF3)2Pz]Cu}3 reacts with acetylene to produce the 2:1 copper(i) acetylene complex, Cu4(μ-[3,5-(CF3)2Pz])4(μ-HCCH)2. Related Cu4(μ-[4-Br-3,5-(CF3)2Pz])4(μ-HCCH)2 and Cu4(μ-[4-Cl-3,5-(CF3)2Pz])4(μ-HCCH)2 have also been isolated using the corresponding copper(i) pyrazolate and acetylene. The 1:1 adducts Cu2(μ-[3,5-(CF3)2Pz])2(HCCH)2 and Cu2(μ-[4-Br-3,5-(CF3)2Pz])2(HCCH)2 are significantly less stable to the acetylene loss and can be observed in solution at low temperatures under excess acetylene. The X-ray crystal structures of 2:1 and 1:1 complexes, Cu4(μ-[3,5-(CF3)2Pz])4(μ-HCCH)2 and Cu2(μ-[4-Br-3,5-(CF3)2Pz])2(HCCH)2 are reported. Raman data show a reduction in CC stretching frequency by about ～340 and ～163 cm-1 in the 2:1 and 1:1 Cu(i)/acetylene complexes, respectively, from that of the free acetylene. Copper(i) pyrazolate complexes of the terminal alkynes, phenylacetylene, 1,8-nonadiyne, and 1,7-octadiyne are also reported. They form adducts involving one copper atom on each alkyne moiety. The {μ-[3,5-(CF3)2Pz]Cu}3 is also a very versatile and competent catalyst for alkyne transformations as evident from its ability to catalyze the alkyne C(sp)-H bond carboxylation chemistry with CO2, azide-alkyne cycloadditions leading to 1,2,3-triazoles including the use of acetylene itself as a substrate, and thiol addition to phenylacetylene affording vinyl sulfides.

Gem-Heterosubstituted (stannyl)methylsilanes as synthetic equivalents of functionalized α-stannyl(methyl) anions

α-Heterosubstituted silyl derivatives, such as phenylthio-, phenylseleno- and benzotriazolyl-stannyl silanes, react with aldehydes under tetra-n-butylammonium fluoride (TBAF) catalysis, leading to α-substituted-βhydroxy stannanes, able to behave as precursors of Z- and E-olefins, generated by deoxystannylation. This reactivity shows the capability of such heterosubstituted silanes to act as masked carbanions through a mild functionalization of the carbon-silicon bond.

Structural elucidation of supported Rh complexes derived from RhCl(PPh3)3 immobilized on surface-functionalized SBA-15 and their catalytic performance for C-heteroatom (S, O) bond formation

The local structures of rhodium complexes derived from the immobilization of Wilkinson's complex, RhCl(PPh3)3, on SBA-15 silica functionalized with primary–amine, secondary–amine, or diphenylphosphine groups within the mesoporous channels were characterized by a series of techniques including XRD, HR-TEM, multinuclear (13C/29Si/31P) solid-state NMR, 2D 31P{1H} HETCOR NMR, XPS, and Rh K-edge EXAFS. Immobilization of RhCl(PPh3)3 through covalent bond formation with different functional groups grafted to the silica surface lead to variations in the local structure of the Rh center that has important implications for catalysis. The immobilized Rh complexes demonstrated high activity for the addition of alkynes with thiols (hydrothiolation) or sulfonic acids (hydrosulfonation) with excellent regio- and stereoselectivity under mild reaction conditions. This work demonstrates the elucidation of the local structure of the immobilized Rh complexes requires a complimentary multi-technique characterization approach that probes both the metal center itself and surrounding ligands.