7559-49-1

Upstream product

• 39549-10-5 1-[(4-methylphenyl)sulfanyl]pyrrolidine-2,5-dione 
• 20277-69-4 sodium methansulfinate 
• 106-45-6 para-thiocresol 
• 124-63-0 methanesulfonyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 10439-23-3 4-methylbenzenesulfinyl chloride 
• 6873-87-6 N-butyl-4-methylbenzene-1-sulfinamide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 10409-07-1 bis(4-methylphenyl)disulfone 
• 103-19-5 di(p-tolyl) disulfide 
• 67-68-5 dimethyl sulfoxide 
• 24398-14-9 1-[(diethylamino)sulfanyl]-4-methylbenzol 
• 118063-38-0 Methanethiosulfonic acid S-(2,4-dinitro-phenyl) ester 
• 933-00-6 p-methylbenzenesulfenyl chloride 

Downstream Products

• 131947-30-3 2-phenyl-3-(4-tolylthio)imidazo<1,2-a>pyridine 

Relevant academic research and scientific papers

Electrochemical cross-coupling reactions of sodium arenesulfinates with thiophenols and phenols

A green electrochemical oxidative cross-coupling protocol for the generation of thiosulfonates and sulfonate esters using sodium arenesulfinates and thiophenols/phenols is disclosed. The protocol involves using inorganic and non-toxic NaI as both redox catalyst and supporting electrolyte at room temperature without oxidant and base. The reactions provide good yields of products and tolerate broad substrate scope. The mechanistic studies revealed that the reactions proceed via a radical pathway for the formation of SO2–S and SO2–O bonds.

Direct conversion of sulfinamides to thiosulfonates without the use of additional redox agents under metal-free conditions

Direct conversion of sulfinamides to thiosulfonates is described. Without the use of additional redox agents, the reaction proceeds smoothly in the presence of TFA under metal-free conditions. This protocol possesses many advantages such as odourless and stable starting materials, broad substrate scope, selective synthesis, and mild reaction conditions. This journal is

Atom transfer radical addition to styrenes with thiosulfonates enabled by synergetic copper/photoredox catalysis

A synergetic copper/photoredox catalyzed ATRA of styrenes and thiosulfonates is developed. Besides aryl ethylenes, the challenging α-substituted styrenes were employed to construct the benzylic quaternary carbon centers. Owing to the mild conditions as well as the high level of substrate compability, this ATRA could be applied to derivatize bioactive natural products in late stage, and to install fluorophores across alkenes. The mechanistic studies reveal sulfonyl radicals as the key intermediate in the transformation.

Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3·OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates

The BF3·OEt2-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O)2 bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation. What is more, this transformation can also be applied practically as a gram-scale reaction and to the two-step synthesis of sulfone and sulfonamide in one pot in situ using thiosulfonate as an intermediate.

Synthetic method for preparing thiosulfonates on basis of sulfinic acid sodium salt disproportionated reaction

The invention relates to a synthetic method for preparing thiosulfonates on the basis of a sulfinic acid sodium salt disproportionated reaction. The preparation method comprises the steps that sulfinic acid sodium salts serve as the raw materials, boron trifluoride diethyl etherate serves as accelerant, dichloromethane serves as solvent, and by means of a disproportionation coupled reaction, a thiosulfinate compound with good biological activity is synthesized; two different sulfinic acid sodium salts serve as the raw materials, and by means of a crossed disproportionation coupled reaction method, an asymmetric thiosulfinate compound can be synthesized. By means of a one-pot method and a two-step method, and by means of a thiosulfonates intermediate prepared on site, a sulfones compound and a sulfonamides compound can be synthesized by directly starting from sulfinic acid sodium salts. Accordingly, a synthetic route for preparing thiosulfonates on the basis of the sulfinic acid sodiumsalt disproportionated reaction is provided for the first time, operation is easy, raw materials are easy to obtain, the condition is mild, no metal catalyst is needed, no additional oxidant or reductant is needed, and the prepared thiosulfonates can have the good biological activity, and can also serve as the intermediate of the reaction to be applied to organic synthesis.

Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide

A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).

Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates

A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.

Oxidative coupling of dichalcogenides with sodium sulfinates via copper-catalyzed cleavage of s-s and se-se bonds

A copper-catalyzed sulfonylation of disulfides was achieved using sodium sulfinates in air. The reaction formed various sulfur-sulfone bonds efficiently and afforded thiosulfonates in good yields. Selenosulfonates could also be prepared with this procedure. Furthermore, both chalcogenide groups on the dichalcogenides were available in these reactions.

Copper-catalyzed synthesis of thiosulfonates by oxidative coupling of thiols with sodium sulfinates

The copper-catalyzed sulfonylation of thiols was performed by using sodium sulfinates under an oxygen atmosphere. The procedure afforded thiosulfonates in good yields by using a CuI-Phen?H2O (Phen = 1,10-phenanthroline) catalyst and tolerated numerous combinations of arene- and alkanethiols with sodium sulfinates. Furthermore, it was found that the coupling of diaryl disulfides with sodium arylsulfinates proceeded in air and both sulfide groups on the disulfide were available.

Sc(OTf)3-catalyzed synthesis of thiosulfonates in ionic liquid-water

The first example of Sc(OTf)3-catalyzed sulfenylation of sodium sulfinates with N-(organothio)succinimides in ionic liquids (ILs) and water cosolvent system was developed, achieving thiosulfonates in moderate to excellent yields. Additionally, Sc(OTf)3/ILs could be recovered easily after the reactions and reused without a significant loss in the catalytic activity. Thus, the present protocol represents an interesting complement to known methods for thiosulfonates synthesis.