84314-22-7

Upstream product

• 629-27-6 1-Iodooctane 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 98-59-9 p-toluenesulfonyl chloride 
• 111-85-3 n-chlorooctane 
• 111-83-1 1-bromo-octane 
• 624-31-7 4-tolyl iodide 
• 1065131-41-0 n-octanesulfonyl hydrazide 
• 36651-88-4 N-(4-methylphenylazo)pyrrolidine 

Downstream Products

• 154581-55-2 (E/Z)-1-benzyloxy-3-(4-tolylsulfonyl)decene 
• 115085-77-3 3-heptyl-2-phenylfuran 
• 85615-63-0 (Z)-2-octenyl p-tolyl sulfone 
• 111895-46-6 (Z)-1-tosyl-2-nonene 
• 100696-60-4 (E)-2-octenyl p-tolyl sulfone 
• 111895-50-2 (E)-1-methyl-4-(oct-1-en-1-ylsulfonyl)benzene 
• 408496-45-7 1-[(diethylphosphonate)methyl]-4-(octane-1-sulfonyl)-benzene 
• 156060-82-1 1-(bromomethyl)-4-(octane-1-sulfonyl)benzene 

Relevant academic research and scientific papers

On the important transition of sugar-based surfactant as a microreactor for C-S coupling in water: From micelle to vesicle

A reversible, temperature-induced micelle-to-vesicle transition of a sugar-based pseudogemini surfactant (C11D12) was employed for copper-catalyzed C-S coupling in water. The phase behavior and morphology of the C11D12 aqueous solution were investigated by DLS and cryo-TEM. The aggregates undergo a series of transitions upon increasing the temperature: spherical micelles were initially transformed into large vesicles, but they eventually transformed into smaller vesicles. The vesicular catalytic protocol accommodates an excellent substrate scope with moderate to high yields. The mechanisms of temperature-induced aggregate transition and vesicular catalysis were elucidated by experimental results and DFT calculations. It was revealed that the charge layer of the vesicle grants stronger nucleophilicity to the PhSO2-Cu-D12Ga intermediate. Furthermore, the aqueous reaction medium can be recycled and reused several times after easily separating the precipitated product.

Multicomponent Reductive Cross-Coupling of an Inorganic Sulfur Dioxide Surrogate: Straightforward Construction of Diversely Functionalized Sulfones

Conventionally, sulfones are prepared by oxidation of sulfides with strong oxidants. Now, a multicomponent reductive cross-coupling involving an inorganic salt (sodium metabisulfite) for the straightforward construction of sulfones is disclosed. Both intramolecular and intermolecular reductive cross-couplings were comprehensively explored, and diverse sulfones were accessible from the corresponding alkyl and aryl halides. Intramolecular cyclic sulfones were systematically obtained from five- to twelve-membered rings. Naturally occurring aliphatic systems, such as steroids, saccharides, and amino acids, were highly compatible with the SO2-insertion reductive cross-coupling. Four clinically applied drug molecules, which include multiple heteroatoms and functional groups with active hydrogens, were successfully prepared via a late-stage SO2 insertion. Mechanistic studies show that alkyl radicals and sulfonyl radicals were both involved as intermediates in this transformation.

Aryl alkyl sulfone compound and reducing coupling method for constructing sulfone compounds

The invention discloses an aryl alkyl sulfone compound shown as a formula (1) and a synthetic method thereof. The aryl alkyl sulfone compound is prepared by taking an aromatic iodide, an inorganic sulfur reagent and an alkyl bromide as reaction raw materials to carry out reacting in a solvent under action of alkali, a catalyst, a ligand, a reducing agent and an additive. According to the invention, an inorganic sulfur reagent is used as a sulfur source to construct the aryl alkyl sulfone compound in one step under catalysis and reduction conditions, so that the defect in synthesizing the arylalkyl sulfone compound by conventional oxidation of thioether is avoided. The aryl alkyl sulfone compound developed by the invention can be used for synthesizing aryl alkyl sulfone medicines.

A practical synthesis of aryl sulfones via cross-coupling of sulfonyl hydrazides with aryltriazenes using copper/ionic liquid combination

A new and efficient approach adopting copper-catalyzed cross-coupling of sulfonyl hydrazides with aryltriazenes has been developed to synthesize aryl sulfones using Br?nsted acidic ionic liquid as promoter under ambient conditions. The process employs stable and easy to handle reacting partners, and is endowed with broad substrate scope.

Efficient synthesis of aliphatic sulfones by Mg mediated coupling reactions of sulfonyl chlorides and aliphatic halides

Sulfonyl chlorides were reduced to anhydrous sulfinate salts with magnesium under sonication. These sulfinates were alkylated to sulfones with alkyl chlorides in the presence of catalytic sodium iodide under sonication. A variety of aliphatic sulfones was efficiently prepared by this one-pot two-step procedure.

Revisiting nucleophilic substitution reactions: Microwave-assisted synthesis of azides, thiocyanates, and sulfones in an aqueous medium

A practical, rapid, and efficient microwave (MW) promoted synthesis of various azides, thiocyanates, and sulfones is described in an aqueous medium. This general and expeditious MW-enhanced nucleophilic substitution approach uses easily accessible starting materials such as halides or tosylates in reaction with alkali azides, thiocyanates, or sulfinates in the absence of any phase-transfer catalyst, and a variety of reactive functional groups are tolerated.

Organic reactions in ionic liquids: A new method for the synthesis of alkyl aryl sulfones by alkylation of sodium arenesulfinates with unactivated alkyl chlorides

A new method is reported for the synthesis of alkyl aryl sulfones by alkylation of sodium arenesulfinates with unactivated alkyl chlorides using ionic liquid based on 1-butyl-3-methylimidazolium tetrafluoroborate (BmimBF 4) mixed with water (2:1) as reaction media. The ionic liquid can be reused and the procedure gives the sulfones in moderate yields.

1-Benzyloxy-3-(p-tolylsulfonyl)alkenes as enal β-anion equivalents. Synthesis of 2,3-disubstituted furans

An efficient three-step method is described for the synthesis of 2,3-disubstituted furans from (p-tolylsulfonyl)alkanes 6 and 2-benzyloxyethanal.

A Novel Synthesis of Alkyl Aryl Sulfones via the Telluride Ion-Assisted Coupling of Arenesulfonyl Chlorides with Alkyl Halides

Arenesulfonyl chlorides undergo a facile one-pot coupling reaction with primary alkyl iodides and benzyl halides through the telluride ion-induced polarity reversal, giving the corresponding alkyl aryl sulfones in acceptable yields.

SIMPLE AND CONVENIENT METHOD FOR THE SYNTHESIS OF SULFONES USING POLYETHYLENE GLYCOLS OR THEIR DIALKYL ETHERS AS SOLVENTS OR CATALYSTS.

Various alkyl p-tolyl sulfones were prepared in good yields under mild conditions in the presence of polyethyene glycols or their dialkyl ethers as solvents or catalysts.