Article
Chemistry, Organic
Danish Khan, Iram Parveen
Summary: A new family of phosphine-free Amino-chroman-4-one bidentate ligands were successfully synthesised and characterised, showing efficient catalytic activity in C-C bond formation. They demonstrated excellent performance in Suzuki-Miyaura and Mizoroki-Heck coupling reactions, with a broad range of substrates well tolerated under the optimized reaction conditions. Mass spectrometry was used to characterize the metal complex and intermediates formed in the catalytic cycle, supporting the reaction mechanism.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Elvis N. Nishida, Elder C. Leopoldino, Laize Zaramello, Higor A. Centurion, Renato Goncalves, Ricardo F. Affeldt, Carlos E. M. Campos, Bruno S. Souza
Summary: A novel Pd(II)-polymeric pre-catalyst was successfully prepared and demonstrated good activity in the Suzuki-Miyaura coupling reaction. The catalyst showed recyclability and its performance was affected by the concentration of the cross-coupling partners. The presence of oxygen was found to be crucial in preventing the formation of inactive Pd(0) aggregates.
Review
Chemistry, Physical
Marco Kruppa, Thomas J. J. Mueller
Summary: The Masuda borylation-Suzuki coupling (MBSC) sequence enables the direct formation of (hetero)biaryls from readily available (hetero)aryl halides under mild conditions, providing access to diverse symmetric and asymmetrically substituted scaffolds. This review summarizes the development and improvements of the MBSC sequence over the past two decades.
Article
Chemistry, Physical
Xiaowen Guo, Haihong Wu, Peng Wu, Mingyuan He, Yejun Guan
Summary: This study investigates the particle size effect of Pd catalysts on the reductive etherification of furfural. It is found that Pd nanoparticles larger than 3 nm are suitable for one-step reductive etherification. Based on this finding, a Pd/ZSM-5 bifunctional catalyst is prepared by introducing amino organosilane, which successfully achieves one-pot synthesis of ether via reductive etherification and direct etherification, while suppressing undesired side-reactions.
GREEN ENERGY & ENVIRONMENT
(2023)
Article
Chemistry, Organic
Mingzhong Cai, Gang Xie, Zhaotao Xu, Bin Huang
Summary: An efficient heterogeneous palladium-catalyzed Suzuki coupling reaction has been developed for the synthesis of aryl ketones from aromatic acids and arylboronic acids. The reaction proceeds smoothly in toluene at 110 degrees C using MCM-41-bound bidentate phosphine palladium complex as catalyst, providing moderate to excellent yields. The catalyst can be reused multiple times without significant decrease in its catalytic activity.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Sheng-Qi Qiu, Yu Chen, Xiang-Jun Peng, Shi-Jiang He, Jun Kee Cheng, Yong-Bin Wang, Shao-Hua Xiang, Jun Song, Peiyuan Yu, Junmin Zhang, Bin Tan
Summary: In this study, we achieved the arene-alkene Suzuki-Miyaura coupling reaction between hindered aryl halides and vinyl boronates by designing appropriate ligands and reaction parameters. The axially chiral acyclic aryl-alkenes obtained exhibited remarkable efficiency, enantioselectivity, and E/Z selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Eduam O. Boeira, Caroline B. Pla, Fabiano S. Rodembusch, Angelica Moro
Summary: In this study, the arylation of Troger's base was achieved through the Suzuki cross-coupling reaction using aqueous micellar catalysis. The developed reaction conditions allowed for the preparation of various Troger's base derivatives with low catalytic loading of Pd(OAc)(2) catalyst and under environmentally friendly aqueous conditions.
Article
Nanoscience & Nanotechnology
Chidharth Krishnaraj, Himanshu Sekhar Jena, Kuber Singh Rawat, Johannes Schmidt, Karen Leus, Veronique Van Speybroeck, Pascal Van Der Voort
Summary: This study synthesized and compared the performance of 2D imine COFs as catalysts, finding that Pd@TTA-DFB COF exhibited fast reactivity but low stability, Pd@TTA-DFP COF had the highest stability but slowest reactivity, and Pd@TTA-TBD COF showed the best overall performance. Experimental and computational results indicated that the reduction from Pd(II) to Pd(0) is a key step in determining the catalytic activity of COFs.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Engineering, Environmental
Siqi Ji, Xiaowen Lu, Mingyang Zhang, Leipeng Leng, Hongxue Liu, Kuibo Yin, Chang Xu, Cheng He, J. Hugh Horton, Jiangwei Zhang, Zhijun Li
Summary: A catalyst with atomic palladium atoms supported over UiO-66-NH2 demonstrates extraordinary catalytic performance in terms of activity, selectivity, and yield. The high catalytic activity is attributed to optimized electronic metal-support interactions and positive valence state of the palladium atoms.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Applied
Feng Ma, Xian-Tao Wu, Le-Wei Miao, Fuxing Sun, Yi-Jun Jiang, Peng Chen
Summary: A general, efficient, and regioselective protocol for the synthesis of trifluoromethylated bis(carbazolyl)methanes has been developed. This metal-free transformation proceeds smoothly under air atmosphere and has a broad scope for both reaction partners. This method can also be extended to the synthesis of difluoromethylated and chlorodifluoromethylated bis(carbazolyl)methanes.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Lukas Hoff, Gleb A. Chesnokov, Anthony Linden, Karl Gademann
Summary: This study presents a thorough mechanistic investigation of the Pd-catalyzed and Ag-mediated cross-coupling reaction between monosubstituted tetrazine and boronic acids. Through kinetic analyses, isolation of intermediates, and computational methods, insights into the mechanism were obtained. The study also demonstrated the experimental confirmation of a highly electron-deficient ligand and the impact of mechanistic understanding on the generality of the reaction scope through a data-driven workflow.
Article
Chemistry, Organic
Santanu Ghora, Chinnabattigalla Sreenivasulu, Gedu Satyanarayana
Summary: An efficient one-pot domino synthesis method for quinolines is described, utilizing palladium catalysis to couple iodoanilines with allylic alcohols. The synthesis process involves intermolecular Heck coupling, intramolecular condensation, and dehydrogenation sequence, all conducted in water as a green solvent. This method demonstrates broad substrate scope and can also be applied for the synthesis of deuterated quinolines through a deuterium-exchange process.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Yuichiro Kawamoto, Toyoharu Kobayashi, Hisanaka Ito
Summary: Stachyodin A, with a unique spirotetrahydrofuran ring system, was isolated from the roots of Indigofera stachyodes in 2018. The first total synthesis of racemic stachyodin A was accomplished in 14 steps.
Article
Chemistry, Organic
Yogesh Thopate, Richa Singh, Sumit K. Rastogi, Arun K. Sinha
Summary: In this study, a multicomponent 5 step reaction was developed to synthesize stilbene/biaryl-quinolone hybrid molecules. The combination of Gould-Jacobs reaction and Heck reaction, along with the use of diphenyl ether as a reaction solvent, allowed for the convergence of five steps into one pot. This method not only generated C-C and C-N bonds, but also cleaved C-O and C-C bonds, demonstrating its potential in the synthesis of hybrid molecules.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Weixu Lu, Xiaoqiang Yu, Ming Bao
Summary: In this paper, a group of copper-based ternary deep eutectic solvents (Cu-DESs) were synthesized and applied in Glaser-type homo- and cross-coupling of terminal alkynes. These reactions occurred under exogenous-ligand-free, base-free, and additive-free conditions, providing satisfactory to excellent yields (up to 99%) under mild conditions. The Cu-DESs can be recycled eight times, with water being the only by-product, complying fully with the principles of green chemistry.
Article
Chemistry, Organic
Fayun Chen, Li-Xia Quan, Anxi Zhou, Congbin Ji, Yanhong Li, Xianhong Zhu, Liu-Liang Mao, Jie-Ping Wan
Summary: An efficient and facile strategy was developed for the synthesis of 6-(sulfonylmethyl)phenanthridines and its derivatives through tandem sulfonylation cyclization of vinyl azides. The reaction utilizes accessible and cheap K2S2O5 as the sulfur dioxide source and achieves moderate to excellent yields with easy operation and gram-scale synthesis, as well as good functional-group tolerance.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Huan Gao, Liyun Zhou, Jie-Ping Wan, Yunyun Liu
Summary: Rongalite has been used as a cheap and efficient carbonsynthonfor the synthesis of divergent N-heteroaromatics, including differentpyridines and quinolines. The selective synthesis of different productscan be achieved by employing enaminones or enaminones/anilines asreaction partners. Rongalite displays an evident advantage in providing products with considerably higher product yields under milder conditions compared with the reaction using conventional aldehyde synthons. The GC-MS analysis of the reaction process has been performed to probe the possible reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shanghui Tian, Yunyun Liu, Changfeng Wan, Jie-Ping Wan, Guifeng Hao
Summary: A simple and efficient method for synthesizing cinnolines is developed by reacting readily available enaminones and aryl diazonium tetrafluoroboronates. The reactions produce diversified cinnolines without the need for catalysts or additives by heating in dimethyl sulfoxide. Furthermore, the investigation of their anti-inflammatory activity reveals promising candidates, p-chlorobenzoyl (3f) and p-nitrobenzoyl (3j) cinnolines.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Demao Chen, Liyun Zhou, Chengping Wen, Jie-Ping Wan
Summary: By using readily available enaminones, aryl hydrazine hydrochlorides, and alkynes, a chemo-selective three-component synthesis of atropisomeric N-(o-alkenylaryl)pyrazoles was efficiently achieved with rhodium catalysis. Unlike the Satoh-Miura reaction, which uses pre-prepared N-phenyl pyrazoles and alkynes as substrates for alkyne-based C-H benzannulation, this three-component protocol demonstrates unprecedented selectivity of C-H alkenylation by blocking the second round metal alkenylation with the key protonation step in the presence of acids.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yan Lin, Jie-Ping Wan, Yunyun Liu
Summary: This article describes a facile cascade reaction for the site-selective synthesis of 2-cyanochromones. By using simple o-hydroxyphenyl enaminones and potassium ferrocyanide trihydrate (K4[Fe(CN)6]3·3H2O) as starting materials, and I2/AlCl3 as promoters, the products are obtained through tandem chromone ring formation and C-H cyanation. The unconventional site selectivity is attributed to the in situ formation of 3-iodochromone and a formal 1,2-hydrogen atom transfer (HAT) process. Additionally, the synthesis of 2-cyanoquinolin-4-one has been achieved by employing the corresponding 2-aminophenyl enaminone as the substrate.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Demao Chen, Changfeng Wan, Yunyun Liu, Jie-Ping Wan
Summary: A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been developed via the reactions of enaminones, hydrazine hydrochloride, and internal alkynes using Rh catalysis. The cascade reactions demonstrate the remarkable high-order bond functionalization, involving the transformation of aryl C-H, ketone C=O, and alkenyl C-N bonds in the enaminones. This study highlights the individual advantage of enaminones in the design of novel and efficient synthetic methods.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Changfeng Hu, Jingyi Song, Wumeng Jin, Wenqiang Wang, Hongjin Bai, Cuiyun Wu, Lirong Shen
Summary: Walnut oil, rich in polyunsaturated fatty acids, has many health benefits. The synthesis and accumulation of walnut oil in the embryo development process may be influenced by a special mechanism for triacylglycerol biosynthesis. Shotgun lipidomics analysis revealed that triacylglycerol synthesis in walnut kernels occurred before 84 days after flowering and was enhanced between 84 and 98 days. Acyl editing through phosphatidylcholine played a role in the flux of fatty acids for triacylglycerol synthesis. Therefore, triacylglycerol biosynthesis in walnut kernels is directly linked to lipid metabolism.
Article
Engineering, Environmental
Mingying Liu, Ju Mu, Miao Wang, Changfeng Hu, Jinjun Ji, Chengping Wen, Dayi Zhang
Summary: Microplastics (MPs) accumulation and its impacts on lipid metabolism in mouse liver were investigated in this study using lipidomics and Raman spectroscopy. The results showed that polypropylene-MPs induced lipid droplet accumulation in the liver and significantly altered lipid metabolic profiles, including triglycerides, fatty acids, free fatty acids, and lysophosphatidylcholine. The presence of polypropylene-MPs also affected membrane properties and cellular lipid storage and oxidation regulation. The findings provide insights into the toxicities and risks of polypropylene-MPs to mammals.
JOURNAL OF HAZARDOUS MATERIALS
(2023)
Article
Chemistry, Organic
Xiao Xiao, Puren Han, Jie-Ping Wan, Jianchao Liu
Summary: An efficient and general method for the synthesis of indolyl-C-glycosides has been developed. The method exhibits excellent stereoselectivity, a wide range of substrate applicability, and mild reaction conditions. It has also been successfully applied to large-scale reactions and diversified synthetic transformations.
Article
Chemistry, Multidisciplinary
Zukang Zhong, Lihua Liao, Yunyun Liu, Ming Zhang, Jie-Ping Wan
Summary: The annulation reactions of enaminones with quinonediimides/quinoneimides for selective synthesis of indoles and 2-aminobenzofurans have been realized. Indoles were obtained via HNMe2-elimination-based aromatization with Zn(ii) catalysis, while 2-aminobenzofurans were produced via dehydrogenative aromatization with Fe(iii) catalysis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Dingsheng Cao, Chaoli Wang, Jie-Ping Wan, Chengping Wen, Yunyun Liu
Summary: This paper describes the trifunctionalization of tertiary enaminones, specifically the selective gem- and vicinal diphosphorylation, enabling the synthesis of tunable alpha,alpha- and alpha,beta-diphosphoryl ketones. Additionally, the phosphorylation of the C-N bond with improved substrate tolerance has been achieved.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Demao Chen, Liyun Zhou, Yunyun Liu, Jie-Ping Wan
Summary: The direct three-component reactions of enaminones, aryl hydrazine hydrochlorides, and internal alkynes via Rh(iii) catalysis have enabled the synthesis of N-naphthyl pyrazoles. The use of simple substrates in these synthetic reactions results in the simultaneous construction of dual cyclic moieties, including a pyrazole ring and a phenyl ring, through the sequential formation of two C-N and three C-C bonds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Baoli Zhao, Xiaoting Yin, Haifeng Li, Kai Cheng, Jie-Ping Wan
Summary: A metal-free dioxygenative reaction of aryl diazonium salts with aryl alkynes for vicinal diketone synthesis has been developed. The major advantages of this synthetic method are aerobic oxygenation and organic dye-based photocatalysis. A photoredox mechanism involving free radical dioxygenation is proposed based on rational control experiments.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Organic
Jianchao Liu, Jie-Ping Wan, Yunyun Liu
Summary: This review highlights the recent progress in the development of electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens. It covers various reactions such as oxychalcogenation, carbochalcogenation, aminochalcogenation, halochalcogenation, and dichalcogenation. These studies are of great significance in the field of organic synthesis chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Jingfeng Ye, Yunyun Liu, Jin Luo, Jie-Ping Wan
Summary: The synthesis of polyfunctionalized alkenes has been achieved through the transformation of enaminones, disulfides, and alcohols without the use of transition metals. Furthermore, the application of the alkene products in the synthesis of various sulfenyl heteroaryls has been demonstrated.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
