26190-67-0

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 536-74-3 phenylacetylene 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 4124-41-8 p-toluenesulfonylanhydride 
• 98-86-2 acetophenone 

Downstream Products

• 104-15-4 toluene-4-sulfonic acid 
• 98-86-2 acetophenone 
• 38212-14-5 1-isobutylvinylbenzene 
• 910896-15-0 2,4-diphenyl-1-(toluene-4-sulfonyl)-1H-pyrrole 
• 31378-03-7 1-phenyl-2-tosylethanone 
• 25944-64-3 diethyl (1-phenylethenyl)phosphonate 
• 16336-45-1 α-phenylthiostyrene 
• 132709-18-3 2-phenylacrylic acid phenyl ester 

Relevant academic research and scientific papers

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.

Photoinduced rearrangement of vinyl tosylates to β-ketosulfones

We developed a photoinduced radical fragmentation and rearrangement of vinyl tosylates that enables efficient formation of β-ketosulfones. This process is based on the photoinitiated homolysis of vinyl tosylate to release a sulfinyl radical from the tosyl group and the subsequent addition of a sulfinyl radical to another vinyl tosylate to form the desired β-ketosulfones. This simple protocol features a broad scope with both aromatic and aliphatic substrates, convenient reagents and operating systems.

Phosphorylation of Alkenyl and Aryl C-O Bonds via Photoredox/Nickel Dual Catalysis

A phosphorylation of alkenyl and aryl C-O bonds at room temperature via photoredox/nickel dual catalysis is reported. By starting from easily available and inexpensive sulfonates, a variety of important alkenyl phosphonates and aryl phosphine oxides are g

A Combination System of p -Toluenesulfonic Acid and Acetic Acid for the Hydration of Alkynes

A simple combination system of p-toluenesulfonic acid/acetic acid has been developed for efficient hydration of alkynes. The corresponding ketones can be obtained in good to excellent yields under mild conditions. The mechanism of the reaction was disclosed unambiguously which was a stepwise process (addition and then hydrolysis). Furthermore, this system was proved to be powerful that has the potential to be used to synthesize vinyl 4-methylbenzenesulfonates.

Addition of sulfonic acids to terminal alkynes catalyzed by a rhodium complex: Ligand concentration-controlled reaction selectivity

A Rh-catalyzed process for the regioselective formation of vinyl sulfonate esters in moderate to high yields through the hydrosulfonation of alkynes with sulfonic acids has been developed. Our synthetic approach is capable of adding a variety of alkynes to a set of sulfonic acids and is amenable to different phosphorus ligands, solvents, and Rh precursors. We control the chemo- and regioselectivity of the reaction to the Markovnikov vinyl sulfonate ester by tuning the concentration of the exogenous ligand, PPh3, which forms the active Rh-P species insitu. At lower PPh3 concentrations, the reaction favors the formation of vinyl sulfonate esters, whereas at higher PPh3 concentrations, the reaction favors the formation of vinylphosphonium salts. We perform Hammett analyses and kinetic isotope effect experiments to determine the steps of the catalytic mechanism. Reaction data for substituted acetylenes indicates syn and anti addition occur across the triple bond. Experiments performed with the vinylphosphonium salt as the exogenous ligand determined that the formation of the salt was not a necessary step in the catalytic mechanism for the direct formation of the vinyl sulfonate esters.

Preparation of α,β-unsaturated esters and amides via external-CO-free palladium-catalyzed carbonylation of alkenyl tosylates

Palladium-catalyzed carbonylation of tosylates with phenyl formate is described. This procedure needs neither external carbon monoxide nor any pressure-resistant apparatus. A variety of cyclic and acyclic alkenyl tosylates can be converted into the corresponding phenyl esters in good yields. Furthermore, this method is effective for the one-pot synthesis of α,β-unsaturated amides.

Gold-catalyzed addition of sulfonic acids to alkynes to form vinyl sulfonates

In the presence of a catalytic amount of (Ph3P)AuNO3 and phthalimide, the addition of toluenesulfonic acid or methanesulfonic acid to alkynes has been shown to proceed and gives vinyl tosylates and vinyl mesylates in good yields and

Kumada coupling of aryl and vinyl tosylates under mild conditions

Aryl and alkenyl tosylates are easily prepared, inexpensive and, thus, attractive for transition-metal-catalyzed couplings, but their reactivity is low. We report examples of mild, palladium-catalyzed coupling of aryl, alkenyl, and alkyl Grignard reagents with aryl and alkenyl tosylates. The resulting biaryls, vinylarenes, and alkylarenes were isolated in good to excellent yield. These couplings were conducted with a nearly equimolar ratio of the two reactants, and many examples were conducted at room temperature.

Comparative Substituent Effects of Tosyloxy, Benzyloxy, and Phosphoryloxy Substituents in Carbocation Formation. Acid-Catalized Hydration of Vinyl Tosylates, Benzoates, and 1,1-Ditosylates

Kinetc results for theacid-catalized hydration of alkenyl esters CH2=C(OX)R (X = Bz, Ts) and literature data for X = Ac and PO3Et2 are analyzed by the excess acidity method, and it is concluded that all the substrates react by the AdE2 mechanism of rate-limiting proton transfer to the double bond.Average substituent parameters ?p+ derived for the groups OBz, OAc, and OPO3Et2 of -0.18, -0.16, and -0.20, respectively, are similar and indicate these groups are modestly effective electron donors, while the average values of 0.08 for the OTs group indicates this to be a net electron withdrawing group.Hydrolysis of t-BuCH=C(OTs)2 requires much stronger acid; it has kH+/kD+ = 5.75 and a low slope of the rate versus acidity plot that is interpreted in terms of rate-limiting protonation of a substrate whose basic oxygens interact strongly with the acid solvent.