1093253-55-4

Upstream product

• 75-75-2 methanesulfonic acid 
• 536-74-3 phenylacetylene 

Downstream Products

• 26926-35-2 Benzoesaeure-methansulfonsaeure-anhydrid 
• 3708-04-1 2-methylsulfonyl-1-phenylethanone 

Relevant academic research and scientific papers

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.

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.

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