Article
Chemistry, Organic
Tong Li, Chaoxing Cui, Yuxia Zhang, Xixi Song, Zechao Wang, Junbiao Chang
Summary: A new method for the oxidative aromatization of spiro[2.5]octa-4,7-dien-6-ones using 2-iodoxybenzoic acid (IBX)-dimethyl sulfoxide (IBX-DM-50) as the promoter has been developed. This method allows for the transformation of various substrates with different substituents into aromatization products with high efficiency. It features environmentally friendly reagents, broad substrate scope, broad functional-group tolerance, and mild reaction conditions.
Article
Environmental Sciences
Kyeongnam Kim, Sung-Eun Lee
Summary: The study investigated the combined acute toxicity of 0.1% and 0.5% DMSO with vanadium on zebrafish embryos, showing that the combination of both had a synergistic effect delaying the development of zebrafish embryos and causing pericardial edema.
Article
Chemistry, Physical
Heghine H. Ghazoyan, Zara L. Grigoryan, Shiraz A. Markarian, Vitaly V. Chaban
Summary: Ternary mixtures with functional groups have peculiar solvation properties for fine-tuning the physicochemical properties of solvents. The enrichment of available solvents relies on understanding the mutual affinities and structural features of the components. DMSO content in PN/DMSO/water mixtures plays a significant role in preparing homogeneous mixtures with desired PN molar fractions, and the partially amphiphilic nature of DMSO facilitates the successful interface between PN and water.
JOURNAL OF MOLECULAR LIQUIDS
(2023)
Article
Chemistry, Applied
Yoshikuni Deguchi, Masafumi Kono, Yuto Koizumi, Yukino Watanabe, Michiya Fujita, Yu-ichiro Izato, Atsumi Miyake
Summary: Understanding the decomposition mechanism of DMSO has been the focus of research, revealing new chemical bonds and the reduction of sulfur atoms. Kinetic studies suggest that the main decomposition of DMSO may occur via a radical pathway.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Organic
Nagaraju Vodnala, Sanjay Singh, Chinmoy Kumar Hazra
Summary: This study presents a mild and efficient method for synthesizing symmetrical and unsymmetrical diarylmethanes. The use of DMSO as a carbon source and solvent, along with the incorporation of the -CD2 moiety, allows for the synthesis of a wide range of functionalized diarylmethanes. This protocol has been successfully applied to the synthesis of an anti-breast cancer agent and an anticoagulant agent.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Hao Wang, Zeyu Xi, Shuai Huang, Rui Ding, Yang Gao, Yongguo Liu, Baoguo Sun, Hongyu Tian, Sen Liang
Summary: The convenient preparation method involves the reaction of phenols with nitriles and DMSO in the presence of a catalytic amount of (COCl)2 to yield N-acylbenzoxazines in moderate-to-good yields in CH3CN or chloroform. DMSO acts as a source of HCHO generated from the decomposition of a methoxydimethylsulfonium salt, with a proposed regeneration cycle initiated by a catalytic amount of (COCl)2.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Cardiac & Cardiovascular Systems
Choon Kiat Lim, Motakis Efthymios, Wilson Tan, Matias Ilmari Autio, Zenia Tiang, Peter Yiqing Li, Roger Sik Yin Foo
Summary: The study found that DMSO can significantly enhance direct cardiac reprogramming, potentially being used for treating myocardial infarction. Experimental results indicate that DMSO enhances cardiac reprogramming by inhibiting the CBP/p300 bromodomain.
JOURNAL OF MOLECULAR AND CELLULAR CARDIOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Yichen Sun, Zhibin Hu, Jing Peng, Qixue Qin, Ning Jiao
Summary: The Baeyer-Villiger oxidation is a valuable reaction for converting ketones into esters or lactones. In this study, a novel and efficient approach utilizing I-2 as a catalyst for the oxidative rearrangement of cyclobutenones was presented, resulting in the synthesis of furan-2(5H)-one. Dimethyl sulfoxide (DMSO) was used as a greener oxidant and source of oxygen. The reaction proceeded smoothly with catalytic amounts of iodine, yielding lactones in good yields. Compared to conventional Baeyer-Villiger oxidation reactions, the use of DMSO offers a safer and more versatile alternative.
Review
Biochemistry & Molecular Biology
Hai-Lei Cui
Summary: DMSO, as a low-toxicity, inexpensive and easily accessible solvent, has been extensively used as a versatile reagent for the synthesis of functionalized molecules. The past decade has witnessed impressive achievements in the direct synthesis and modification of heterocyclic compounds using DMSO as a reagent.
Article
Engineering, Chemical
Fei Yan, Xiaohan Guo, Qingying Ye, Ping Li, Juanjuan Qi, Lidong Wang
Summary: In this study, supported molybdenum oxide catalysts were prepared and characterized for the efficient oxidation of DMSO in wastewater using green oxidant, H2O2. The degradation product of DMSO, DMSO2, is environmentally friendly and biodegradable, making it suitable for further removal by biological processes. The results demonstrate the potential of this catalyst for treating industrial wastewater containing DMSO.
SEPARATION AND PURIFICATION TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Jun Dong, Duo Fu, Dongning Sheng, Jiayi Wang, Jiaxi Xu
Summary: The study demonstrates that N-arylethynylsulfonamides can be efficiently oxidized into N-sulfonyl-2-aryloxoacetamides directly with dimethyl sulfoxide (DMSO) serving as both an oxidant and solvent, in the presence of microwave assistance. The reaction mechanism involves nucleophilic attack by DMSO on the ethylic triple bond, leading to the formation of zwitterionic anionic N-sulfonyliminiums that trigger the oxidation reaction. This method provides a straightforward and efficient strategy for the transformation of various N-arylethynylsulfonamides without the need for other electrophilic activators or oxidants.
Review
Chemistry, Organic
Su-Qian Cai, Ke-Feng Zhang, Xiao-Hua Cai
Summary: Dimethyl sulfoxide (DMSO) is a common and cheap polar solvent with low toxicity that has wide applications in organic synthesis. It serves as an efficient reactant and can introduce various functional groups into organic molecules, while also acting as a mild oxidant. Significant advancements have been made in the field of synthetic chemistry using DMSO as a synthon.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Pushpendra Yadav, Annapurna Awasthi, Sabapathi Gokulnath, Dharmendra Kumar Tiwari
Summary: An acid-mediated and DMSO participant one-pot tandem synthesis of 3-substituted-1-aryl-1H-pyrazolo-[3,4-b]quinoline has been achieved from readily available anilines and pyrazolones. This environmentally benign approach enables regioselective construction of valuable heterocycles without the need for transition metals and oxidants. A variety of substituted aryl amines and pyrazolines can be successfully employed in this reaction, accessing a range of pyrazolo[4,3-c]quinolones through a novel cascade mechanism. Additionally, the application and mechanistic studies of this methodology have been demonstrated.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Manuel Gallardo-Villagran, Lucie Paulus, David Yannick Leger, Bruno Therrien, Bertrand Liagre
Summary: This study investigated the effect of DMSO on synoviocytes in RA patients. The results showed that high concentrations of DMSO induced cell death, and even low concentrations of DMSO had a toxic effect on the cells. Therefore, to minimize the impact of DMSO on RA synoviocytes, it is recommended to keep the concentration below 0.05%.
Article
Chemistry, Organic
Suvam Bhattacharjee, Sudip Laru, Payel Ghosh, Alakananda Hajra
Summary: A facile, efficient, and transition-metal-free chemo-divergent C-3 functionalization of 2H-indazoles was developed under aerobic conditions using carboxylic acid and DMSO as the combined source of the carboxylic acid ester group and formylating agent. A series of formylated indazoles and carboxylic acid esters of indazole derivatives were produced in moderate to excellent yields, with mechanistic studies suggesting that the reactions probably proceed through a radical pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Siqi Wang, Jian-Shu Wang, Jun Ying, Xiao-Feng Wu
Summary: A novel Pd-catalyzed carbonylative cyclization reaction of alkene-tethered indoles with phenols or aryl-boronic acids is reported, providing a facile access to indolo[2,1-a]isoquinoline scaffolds. This method utilizes benzene-1,3,5-triyl triformate (TFBen) as a CO surrogate for incorporating a carbonyl group into the indolo[2,1-a]isoquinoline framework, affording various carbonyl-containing indolo[2,1-a]isoquinoline derivatives in good yields.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Ren-Rui Xu, Xiuyu Fang, Xinxin Qi, Xiao-Feng Wu
Summary: A general and straightforward strategy for the synthesis of thioester-substituted oxindoles via a palladium-catalyzed thiocarbonylative cyclization process has been developed. Thioester-substituted oxindoles were obtained in moderate to high yields using sulfonyl chlorides as the sulfur source. Both aryl and alkyl sulfonyl chlorides were well tolerated, and Mo(CO)(6) played a dual role as both a CO source and a reductant in this approach.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zuguang Yang, Jianhua Tang, Chen Li, Zhengkai Chen, Xiao-Feng Wu
Summary: A rhodium(iii)-catalyzed regioselective C2-alkenylation of indoles has been developed for the construction of alpha-CF3 substituted enamines. CF3-imidoyl sulfoxonium ylides (TFISYs) were used as alkenylating agents for the first time, allowing the assembly of a wide array of indolyl- and trifluoromethyl-decorated enamine derivatives in moderate to good yields.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Inorganic & Nuclear
Jian-Xing Xu, Yang Yuan, Xiao-Feng Wu
Summary: In this review, we summarized and discussed the major achievements in transitional metal-catalyzed carbonylative transformations of ethylene. Ethylene hydroformylation, hydroesterification, hydrocarboxylation, hydroaminocarbonylation, dicarbonylation, and multicomponent carbonylation reactions can produce various bulk compounds and fine chemicals, including propanol, alkyl propanoates, succinic diesters, and multifunctionalized C3 compounds.
COORDINATION CHEMISTRY REVIEWS
(2023)
Review
Chemistry, Inorganic & Nuclear
Qingqiang Tian, Xue Yin, Rongjing Sun, Xiao-Feng Wu, Yahui Li
Summary: This review summarizes the main contributions to carbonylative conversion under 1 atm of CO since 1983 and discusses the related literature, demonstrating the attractiveness of carbonylative reactions conducted at 1 atm of CO due to their avoidance of special equipment and risks associated with high-pressure reactions.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Chemistry, Organic
Siqi Wang, Shuwei Li, Liangcai Liu, Jun Ying, Xiao-Feng Wu
Summary: Amide-containing indolo-[2,1-a]isoquinoline scaffolds were synthesized by palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with nitro-arenes. Using Mo(CO)6 as the CO source and reductant, and nitroarenes as the nitrogen source, this reaction yielded various amide-containing indolo[2,1-a]isoquinoline derivatives in good yields. Additionally, the late-stage modifications of bioactive molecules using this protocol were demonstrated.
Article
Chemistry, Multidisciplinary
Zhi-Peng Bao, Youcan Zhang, Le-Cheng Wang, Xiao-Feng Wu
Summary: A novel palladium-catalyzed difluoroalkylative carbonylative cyclization of unactivated alkenes and ethylene gas has been developed for the synthesis of alpha-carbonyl difluoro-modified glutarimides. This method was also applied to the synthesis of GeMigliptin, a medicine approved for the treatment of type 2 diabetes mellitus.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Xing-Wei Gu, Hui-Qing Geng, Xiao-Feng Wu
Summary: An unprecedented and challenging defluorinative arylboration has been achieved using a copper catalyst. This method provides a flexible and facile approach to obtain a diverse range of products from polyfluoroarenes under mild reaction conditions. Furthermore, an enantioselective defluorinative arylboration was successfully realized by employing a chiral phosphine ligand, resulting in chiral products with unprecedented levels of enantioselectivity.
Article
Chemistry, Physical
Han-Jun Ai, Hui-Qing Geng, Xing-Wei Gu, Xiao-Feng Wu
Summary: In this article, a catalytic alkoxycarbonylation method for unactivated alkyl chlorides is reported, which utilizes a pincer manganese catalyst to overcome the difficulties in activating C(sp3)-Cl bonds. This method enables straightforward access to various esters. Mechanistic studies show that the alkyl chlorides are directly activated through oxidative addition reactions.
Editorial Material
Chemistry, Organic
Xiao-Feng Wu, Paul J. Dyson, Bruce A. Arndtsen
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Zuguang Yang, Pinyi Li, Zhengkai Chen, Xiao-Feng Wu
Summary: A rhodium(III)-catalyzed C-H activation/[4+1] annulation reaction has been developed for the synthesis of diverse trifluoroacetimidoyl-substituted 11H-isoindolo[2,1-a]indoles. The reaction cascade involves C-H imidoylmethylation, tautomerization, and AgOAc-mediated C-N bond formation.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Sihao Ling, Yu Zhang, Zhengkai Chen, Xiao-Feng Wu
Summary: A heating-induced desulfuration annulation reaction has been achieved to provide a pathway for the synthesis of biologically important 5-trifluoromethylpyrroles, by reacting pyridinium 1,4-zwitterionic thiolates and CF3-substituted imidoyl sulfoxonium ylides through an unusual ((3+3)-1) pathway under metal-free conditions, with the extrusion of 4-methoxypyridine, sulfur, and DMSO.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Organic
An Da-Lie, Bao Zhi-Peng, Wu Xiao-Feng
Summary: The synthesis and transformation of fluorine-containing organic molecules is an important frontier topic in fluorine chemistry that has profound impacts on life science and material science. Among these, the carbonylative transformation of fluorocarbon-containing substrates is a recently developed carbonylation reaction that still faces many challenges. This review summarizes the progress on carbonylation reactions of fluorocarbon-containing substrates based on transition metal palladium, nickel, and copper catalysis, and discusses representative reactions in detail to understand their mechanisms.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xing-Wei Gu, Yan-Hua Zhao, Xiao-Feng Wu
Summary: Here, a novel methodology using aryl sulfonium salts as aryne precursors for [3 + 2] cycloaddition reactions with azides is described. The reaction, employing readily available arenes as feedstock, exhibits excellent atom economy, environmental friendliness, and high functional group tolerance. Furthermore, the outstanding performance in gram-scale reaction, deuterium labeling, and derivatization reactions suggests potential opportunities for large-scale production and other applications.
Article
Chemistry, Applied
Xing-Wei Gu, Youcan Zhang, Fengqian Zhao, Han-Jun Ai, Xiao-Feng Wu
Summary: The combination of charge-transfer complex and light irradiation provides a promising solution for sustainable chemistry. In this study, a phosphine-catalyzed visible light-induced alkoxycarbonylation reaction was developed, demonstrating high functional group tolerance and excellent chemoselectivity. Additionally, a five-component perfluoroalkylative carbonylation reaction was achieved, allowing the synthesis of β-perfluoroalkyl acyloxy esters from unactivated olefins and perfluoroalkyl iodides.
CHINESE JOURNAL OF CATALYSIS
(2023)
