1574533-07-5

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 657-84-1 sodium tosylate 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 103-19-5 di(p-tolyl) disulfide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent

A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and β-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.

Visible-light-induced surfactant-promoted sulfonylation of alkenes and alkynes with sulfonyl chloride by the formation of an EDA-complex with NaI in water at room temperature

A green and efficient visible-light-induced iodosulfonyl reaction of alkenes in water using an EDA complex strategy at room temperature has been disclosed. The addition of a cationic surfactant allows for the easy formation of colored EDA complexes in water. The hydrophobic effect of the core in the surfactant aggregates, which act as a reaction medium formed by the surfactants themselves in water, plays a significant role in stabilizing the transition state and decreasing the activation energy of the reaction. Remarkably, transition-metal catalysts and organic solvents were not required in this transformation. Moreover, it displayed a broad substrate scope, good functional group tolerance, simple operation, scalability and high chemical selectivity. Thus, it not only provided a green and efficient synthetic strategy for the preparation of β-iodo-substituted sulfone derivatives, but also enriched the investigation of visible-light-induced reactions in water.

Transition-metal-free NaI-mediated reaction of aryl sulfonyl chloride with alkynes: Synthesis of (E)-β-iodovinyl sulfones

A novel protocol for synthesis of (E)-β-Iodovinyl sulfones via NaI-mediated of aryl sulfonyl chloride with alkynes is described, featuring transition-metal-free condition, commercial available substrates, convenient operation, as well as good functional group compatibility. A wide variety of substrate application and good functional group tolerance is provided by this approach, giving multiple (E)-β-Iodovinyl sulfones analogues with excellent yields (up to 98%, >4 g scale).

Iodosulfonylation of Alkynes under Ultrasound Irradiation

(E)-Iodo vinylsulfones are synthesized under ultrasound irradiation using alkynes, sulfonyl hydrazides, potassium iodide and hydrogen peroxide. The key features of this protocol are the speed and efficiency of the reactions, which afford good to excellent

Electrochemical Induced Regio- and Stereoselective Difunctionalization of Alkynes: The Synthesis of (E)-β-Iodovinyl Sulfones

An efficient, green, and oxidant-free electrochemical method for alkyne difunctionalization was described. Using undivided electrochemical cell for iodosulfonylation of alkynes with commercially available iodide radical (NaI), arylsulfonyl radical (ArSOs

Solvent Controlled Transformation between Sulfonyl Hydrazides and Alkynes: Divergent Synthesis of Benzo[b]thiophene-1,1-dioxides and (E)-β-iodo Vinylsulfones

A green, efficient and controllable transformation between sulfonyl hydrazides and alkynes leading to benzo[b]thiophene-1,1-dioxides and (E)-β-iodo vinylsulfones via radical pathway has been developed. The reaction occurs rapidly in the presence of simply H2O2 and KI without the help of any transition metal. The chemoselectivity of the reaction is determined by the solvent in which the process is performed: TFE favors the cyclic product, while H2O medium generates the iodosulfonylative product. Notably, this protocol also represents the first direct approach to the aggregation-induced-emmision (AIE) active benzo[b]thiophene-1,1-dioxides from readily available sulfonyl hydrazides and alkynes in one step. (Figure presented.).

Cobalt-catalyzed stereoselective iodosulfonylation and diiodination of alkynes via oxidation of potassium iodide in air

Cobalt-catalyzed iodosulfonylation of alkynes can be achieved using sodium sulfinates in the presence of KI. This procedure produces numerous stereoselective (E)-β-iodoalkenyl sulfones with good yields and suppresses the formation of diiodoalkenes. Furthermore, when this reaction is performed in the absence of sodium sulfinates, the expected (E)-diiodoalkenes are obtained.

Synthesis of (: E)-β-iodo vinylsulfones via iodine-promoted iodosulfonylation of alkynes with sodium sulfinates in an aqueous medium at room temperature

An efficient molecular iodine-promoted method for the synthesis of (E)-β-iodo vinylsulfones using water as the solvent at room temperature has been developed. This green reaction is fast, operationally simple, environmentally benign and, especially, proceeds under very mild conditions to afford the target products with high regio- and stereoselectivity.

Iodine-catalyzed Sulfonylation of Arylacetylenic Acids and Arylacetylenes with Sodium Sulfinates: Synthesis of Arylacetylenic Sulfones

A highly efficient and generally applicable iodine-catalyzed reaction of arylacetylenic acids and arylacetylenes with sodium sulfinates for the synthesis of arylacetylenic sulfones was developed. The methodology has the advantages of a metal-free strategy, easy to handle reagents, functional group tolerance, a wide range of arylacetylenic acids and arylacetylenes, and easy access to arylacetylenic sulfones. (Chemical Equation Presented).

Aerobic copper-catalyzed synthesis of (E)-alkenyl sulfones and (E)-β-halo-alkenyl sulfones via addition of sodium sulfinates to alkynes

Copper-catalyzed sulfonylation of alkynes using sodium sulfinates in air produced regio- and stereoselectively (E)-alkenyl sulfones. When a CuCl catalyst was employed, the hydrosulfonylation proceeded syn-selectively, and (E)-alkenyl sulfones were synthesized in excellent yields. In contrast, the reaction using CuI catalyst produced (E)-β-haloalkenyl sulfones anti-selectively in the presence of potassium halides. Furthermore, the (E)-β-bromoalkenyl sulfones are possible to convert into various alkenyl sulfones by Suzuki-Miyaura coupling.