14799-03-2

Upstream product

• 98-86-2 acetophenone 
• 3185-99-7 Methyl p-tolyl sulfone 
• 98-59-9 p-toluenesulfonyl chloride 
• 98-83-9 isopropenylbenzene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 536-57-2 p-toluene sulfinic acid 
• 106-45-6 para-thiocresol 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 2028-84-4 p-methylbenzenediazonium chloride 

Downstream Products

• 1344012-82-3 C₃₃H₃₈O₂ 
• 1344012-80-1 1,1-bis(ethoxymethyl)-3-(2-phenylallylidene)cyclobutane 

Relevant academic research and scientific papers

Dioxygen-Triggered Oxosulfonylation/Sulfonylation of Terminal Olefins toward β-Keto Sulfones/Sulfones

A dioxygen-triggered oxosulfonylation/sulfonylation of unactivated olefins to achieve β-keto sulfones/sulfones has been developed. Interestingly, pluralistic mechanisms were found when different types of compounds were applied as substrates, and different products were achieved. The reaction is carried out with a high atomic efficiency in the absence of a metal and a catalyst at room temperature under an air atmosphere. Importantly, as a proof-of-concept, a bioactive molecule was synthesized on a gram-scale level using this method.

Biomimetic photocatalytic sulfonation of alkenes to access β-ketosulfones with single-atom iron site

Biomimetic photocatalysis as an important organic transformation strategy has received increasing attention, with the performances of biomimetic catalysts largely depending on their design. This protocol has been initially used to fabricate a biomimetic photocatalyst of single-atom iron site through coupling carbon nitride with hemin (CNH) for the visible light-promoted sulfonation of alkenes to produce β-ketosulfones with up to 94% yield. The experimental results show that the role of CN in CNH is concentrated on enhancing the separation ability of photogenerated electron pairs and holes to improve the photocatalytic activity and stability. Moreover, the as-prepared photocatalyst of single atom iron can be irradiated under near-infrared light with a satisfactory yield, and is also feasible for the sulfonation reactions of androstenones. Importantly, this biomimetic catalysis-based synthesis system has some merits, namely high catalysis efficiency, favorable recyclability, high turnover number, and excellent functional group tolerance, making it promising for extensive applications in organic transformations for the synthesis of β-ketosulfones to access various bioactive drugs.

A Naphthalimide-Based ND-O-EAc Photocatalyst for Sulfonation of Alkenes to Access β-Ketosulfones Under Visible Light

The development of facile, efficient, cost-effective, and visible light-driven photocatalysts for organic synthetic chemistry has received increasing attention. This protocol has initially synthesized a naphthalimide-based ND-O-EAc visible light photocatalyst for the sulfonation of alkenes to produce β-ketosulfones. Compared with the current photosynthetic strategies, the newly developed catalytic system has some merits, namely high efficiency, gram-scale preparation of low-cost photocatalyst, no metal contamination, wide substrate scope, and green terminal oxidant of air. Moreover, the prepared photocatalyst of ND-O-EAc is feasible for the sulfonation reactions of androstenones. Importantly, such a photocatalysis strategy can easily realize the scale-up synthesis for β-ketosulfone drugs under the mild conditions up to 90 % yield.

Preparation method of oxalyl sulfonyl hydrazide and application of oxalyl sulfonyl hydrazide in olefin sulfonation reaction

The invention belongs to the technical field of organic chemical synthesis and particularly relates to a preparation method of oxalyl sulfonyl hydrazide and application of the oxalyl sulfonyl hydrazide in olefin sulfonation reaction. The preparation metho

Method for preparing beta-keto sulfone or beta-hydroxy sulfone from reaction of substituted olefin and sulfonyl hydrazine derivative

The invention belongs to the technical field of organic chemical synthesis and specifically relates to a method for preparing beta-keto sulfone or beta-hydroxy sulfone from reaction of substituted olefin and sulfonyl hydrazine derivative. The method comprises the following steps: taking substituted olefin and sulfonyl hydrazine derivative as raw materials, taking air as an oxidizing agent and performing oxidizing addition reaction under the existence of photosensitizer and alkali and under the condition of visible light irradiation, thereby generating beta-keto sulfone or beta-hydroxy sulfone.The method provided by the invention is low in cost of raw materials, simple in process, green and safe, efficient and environment-friendly, and suitable for industrial production.

Visible-light promoted aerobic difunctionalization of alkenes with sulfonyl hydrazides for the synthesis of β-keto/hydroxyl sulfones

A practical method has been developed for the conversion of alkenes to β-keto/hydroxyl sulfones by their reaction with sulfonyl hydrazides under metal-free conditions. This reaction proceeds through the oxidative addition of alkenes by sulfonyl radicals that are generated by visible-light induced oxidation of sulfonyl hydrazides. Notaly the reaction uses O2 as the terminal oxidant, instead of metal catalysts or oxidants like TBHP, leading to H2O and N2 as the clean by-products. The key features of this reaction include readily available reagents, mild reaction conditions and broad substrate scope.

PQS-enabled visible-light iridium photoredox catalysis in water at room temperature

An amphoteric PQS-attached photocatalyst has been prepared that undergoes self-aggregation in water into nanomicelles. This covalently bound species enables Ir-based photoredox catalysis to be conducted in the absence of additives or co-solvents. Representative reactions are described using this new catalytic system, which require no additional investment of external energy in the form of heating or cooling. The entire aqueous reaction mixture readily undergoes in-flask recycling and thus, represents a sustainable precious metal technology.

One-pot synthesis of β-hydroxysulfones and its application in the preparation of anticancer drug bicalutamide

An efficient one-pot multistep strategy has been developed, comprising auto-oxidative difunctionalization of alkenes, oxidation of sulfides, and a further reduction of peroxides for the synthesis of complex β-hydroxysulfone derivatives from phenthiols and alkenes. This method has several advantageous characteristics, including readily available substrates, low-cost and environmental benign reagents, nontoxic and renewable solvents, and mild reaction conditions. The application of this transformation to the multigram-scale preparation of the anticancer drug bicalutamide is accomplished.

Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study

A variety of vinyl sulfones were prepared from alkenes and sulfonyl hydrazides via electrochemical oxidative sulfonylation. The reaction proceeds in an experimentally convenient undivided electrochemical cell equipped with graphite and iron electrodes employing KI as a redox catalyst and a supporting electrolyte. Applying extremely high current density up to 270 mA/cm2 permits rapid synthesis in a compact reactor and with small surface area electrodes. A possible reaction mechanism was proposed with the use of cyclic voltammetry. It is the combination of anodic and cathodic processes in this reaction that makes it possible to obtain products under mild conditions with yields from moderate to high.

Iodine-Triggered Aerobic Oxysulfonylation of Styrenes

An iodine-triggered dioxygen activation in oxysulfonylation reactions of unactivated olefins using sulfonyl hydrazides and iodine as catalyst is reported here. In one pot, near quantitative syntheses of β-hydroxysulfones were achieved at 70 °C, within 7 h, in acetonitrile and under aerobic conditions. A plausible mechanism is established by radical trapping and 18O labelling experiments for the operationally simple, efficient and economically viable transformation. The direct activation of aerial oxygen under metal-free and mild conditions is proposed for the oxysulfonylation of olefins. (Figure presented.).