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Controllable Construction of Vinyl Sulfones and β-Keto Selenosulfones via Selective Oxidative Sulfonylation of Alkenes

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Chinese Journal of Chemistry 2024年第12期42卷 1367-1372页

作者： Xiang Liu Yuan Zhang Yi Zheng Changfeng Huang Hua Cao School of Chemistry and Chemical Engineering Guangdong Pharmaceutical UniversityZhongshanGuangdong 528458China

Comprehensive Summary The selective oxidative sulfonylation of alkenes with selenium sulfonate depended on the reaction conditions.The electrochemical C—H sulfonylation proceeded smoothly to afford(E)-vinyl sulfones with good selectivity in an undivided cell without external oxidant.While aerobic trifunctionalization of alkenes occurred in the presence of KI in the air,which providesβ-keto selenosulfones via the formation of C—O,C—S,and C—Se bonds in one-pot.Following control experiments,a plausible mechanism is proposed to rationalize the experimental results.

关键词： Synthetic methods Alkenes Difunctionalization selenylation Sulfonylation

Visible-Light-Promoted Palladium-Catalyzed Cross-Coupling of lodocarboranes with Disulfides and Phenylselenyl Chloride

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Chinese Journal of Chemistry 2024年第2期42卷 129-134页

作者： Shimeng Li Yizhen Liu Zuowei Xie Shenzhen Grubbs Institute and Department of Chemistry Southern University of Science and TechnologyShenzhenGuangdong 518055China

This work describes a general method for the synthesis of a series of sulfenylated and selenylated carboranes at room temperature using readily available iodocarboranes as starting materials via boron-centered carboranyl radicals.Such hypervalent boron radicals are generated by a visible-light-promoted Pd(O)/Pd(I)pathway.They are useful intermediates and can be trapped by disulfides and phenylselenyl chloride for the convenient construction of B-S/Sebonds.

关键词： Carborane Sulfenylation selenylation B-I activation Radical Photocatalysis Boron Selectivity

selenylation Modification of Degraded Polysaccharide from Enteromorpha prolifera and Its Biological Activities

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Journal of Ocean University of China 2018年第2期17卷 445-450页

作者： LV Haitao DUAN Ke SHAN Hu College of Chemistry and Pharmaceutical Sciences Qingdao Agricultural University College of Animal Science and Technology Qingdao Agricultural University

Polysaccharide extracted from Enteromorpha prolifera possessed excellent biological activities,but its molecular weight was greatly high which influenced the activity.Organic Se had higher biological activities and was safer than inorganic Se species.In the present study,Enteromorpha polysaccharide was degraded to low molecular weight by free-radical degradation method of H_2O_2 and ascorbic acid.By single factor and orthogonal experiments,the optimal degradation conditions were reaction time of 2 h,reaction temperature of 50℃,H_2O_2/ascorbic acid(n/n=1:1)concentration of 15 mmol L^(-1),and solid-liquid ratio of 1:50(g mL^(-1)).Then,the degraded polysaccharide was chemically modified to obtain its selenide derivatives by nitric acid-sodium selenite method.The selenium content was 1137.29μg g^(-1),while the content of sulfate radical had no change.IR spectra indicated that the selenite ester group was formed.Degraded polysaccharide selenide was characterized and evaluated for antioxidant,antifungal and antibacterial activities.The results showed that degraded polysaccharide selenide had strong capacity of scavenging DPPH and·OH free radical.It had significant antibacterial properties for Escherichia coli,Bacillus subtilis and Salmonella spp.,and it also had significant antifungal properties for Apple anthrax.The result ascertained degradation and selenylation modification did not change the main structure of polysaccharides.It was possible that free-radical degradation was an effective way for enhancing antioxidant activity to decrease molecular weight of polysaccharides.

关键词： Enteromorpha prolifera polysaccharide free-radical degradation selenylation modification biological activity

Regioselective electrochemical radical cascade cyclization of internal alkynes to selenated and trifluoromethylated dihydropyran

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Science China Chemistry 2023年第11期66卷 3178-3185页

作者： Mingming Yu Tiantian Huang Lin Zhang Muhammad Shabbir Yuhan Gao Yi-Hung Chen Hong Yi Aiwen Lei The Institute for Advanced Studies(IAS) Wuhan UniversityWuhan 430072China National Research Center for Carbohydrate Synthesis Jiangxi Normal UniversityNanchang 330022China

Dihydropyran(DHP)compounds are not only found in natural products and bioactive molecules,but also serve as important precursors in organic synthesis.Nonetheless,traditional methods for the construction of such compounds are usually limited to disubstituted DHPs.To address this synthetic challenge,reported here is an efficient electrochemical strategy toward the selenated and trifluoromethylated DHP compounds.The reaction proceeded smoothly under mild electrolysis conditions.The broad substrate scope(>50 examples)and scalable synthesis demonstrated the complexity-building potential of the strategy.Initial mechanistic studies reveal that cyclization may involve a radical process.This protocol may promote the further development of diversified synthesis of multi-substituted dihydropyran.

关键词： electrochemical organic synthesis dihydropyran cascade cyclization selenylation trifluoromethylation

Practical and sustainable approach for clean preparation of 5-organylselanyl uracils

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Chinese Chemical Letters 2021年第1期32卷 475-479页

作者： Jin-Yang Chen Chun-Tao Zhong Qing-Wen Gui Yuan-Ming Zhou Yang-Yang Fang Kai-Jian Liu Ying-Wu Lin Zhong Cao Wei-Min He College of Chemistry and Chemical Engineering Yangtze Normal UniversityChongqing 408000China Department of Chemistry Hunan University of Science and EngineeringYongzhou 425100China Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation Changsha University of Science and TechnologyChangsha 410114China School of Chemistry and Chemical Engineering University of South ChinaHengyang 421001China

An eco-friendly,sustainable and practical method for the efficient preparation of 5-organylselanyl uracils through the electrochemical selenylation of uracils and dio rganyl diselenides at room temperature under oxida... 详细信息

关键词： selenylation Electrochemistry Diorganyl diselenides Atom-economy Recyclability