Article
Chemistry, Organic
Gaochen Xu, Huan Yan, Sai Zhang, Qinghuan Wu, Jindian Duan, Kai Guo
Summary: A new method using FeCl2 as catalyst for [4+2] annulation of alpha,beta-unsaturated ketoxime acetates with N-acetyl enamides in batch and flow processes is reported. This strategy features a low-cost catalytic system, use of electron-rich olefins, operational simplicity, and broad substrate scope, providing a facile and efficient access to substituted pyridines in moderate to good yields.
Article
Chemistry, Applied
Qinghuan Wu, Gaochen Xu, Yuguang Li, Lei Shen, Zheng Fang, Jindian Duan, Kai Guo
Summary: A Cu(I)-catalyzed [4+2] oxidative annulation reaction between alpha,beta-unsaturated ketoxime acetates and cyclopropanols has been developed for the efficient synthesis of 2,4,5-trisubstituted pyridines in good to moderate yields (28-76%). This method utilizes cyclopropanols as C2 synthons and demonstrates excellent functional group compatibility and scalability. Mechanistic studies support a plausible reaction pathway.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Smruti Ranjan Mohanty, Bedadyuti Vedvyas Pati, Shyam Kumar Banjare, Gopal Krushna Das Adhikari, Ponneri Chandrababu Ravikumar
Summary: A redox neutral Co(III)-catalyzed annulation of alpha,beta-unsaturated oxime ether with alkyne has been reported, resulting in the synthesis of multisubstituted pyridines in good yields without the use of any heavy metal oxidants. The developed methodology tolerates a variety of functional groups and has been successfully applied to the late-stage modification of the bioactive molecule dehydropregnenolone.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhen-Hua Wang, Ping Yang, Yan-Ping Zhang, Yong You, Jian-Qiang Zhao, Ming-Qiang Zhou, Wei-Cheng Yuan
Summary: A Cu(I)-catalyzed ring-opening (3+2) annulation of cyclopropenones with ketoxime acetates has been developed, leading to highly functional 1,2-dihydro-pyrrol-3-one derivatives in good isolated yields. The scalability of the reaction has been demonstrated, and a tentative mechanism for the (3+2) annulation has been proposed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Amitava Rakshit, Hirendra Nath Dhara, Ashish Kumar Sahoo, Tipu Alam, Bhisma K. Patel
Summary: A Pd(II)-catalyzed synthesis of furopyridines has been developed via an unusual N-H/C annulation from beta-ketodinitriles and alkynes. The important features of this method include the participation of both nitrile groups and the concurrent construction of furan and pyridine rings through the formation of multiple bonds. The synthetic applicability is demonstrated through subsequent alterations.
Article
Chemistry, Organic
Xing-Mei Hu, Jing Yang, Jia-Ming Yang, Bi-Na Shao, Rong Huang, Sheng-Jiao Yan
Summary: Here, a novel method is presented for the synthesis of highly functionalized 2,4-diarylpyridines. This method involves a one-pot cascade reaction utilizing alpha,beta-unsaturated ketoxime acetates and enaminones as substrates, encompassing a SET, Michael reaction, oxidation of allyl group carbon, and loss of one proton and one PhNH2. The cascade reaction generates a series of functionalized pyridines, including functionalized asymmetrical 2,4-diarylpyridines. This method provides an efficient alternative to the tedious multi-step syntheses traditionally employed and is suitable for combinatorial and parallel syntheses of pyridine derivatives in a one-pot reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Bodala Varaprasad, Karasala Bharat Kumar, Vidavalur Siddaiah, Pulipaka Shyamala, Lekkala Chinnari
Summary: An efficient and concise method for the synthesis of 2,4,6-triphenyl pyridines was developed using copper-catalyzed oxidative decarboxylative coupling, tolerating various functional groups and providing good to excellent yields.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Fanglian Zhang, Jiameng Liu, Wenjun Luo, Yuping Zhu, Yi Xiao, Shuxian Ma, Feixian Luo, Zhengwang Chen
Summary: An environmentally friendly and transition metal-free method for the annulation of alpha-bromocinnamaldehydes was developed, resulting in the synthesis of 3-formyl-imidazo[1,2-alpha]pyridines and pyrimidines with moderate to excellent yields. This method is characterized by the use of readily available starting materials, transition metal-free conditions, good functional group tolerance, and operational simplicity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Rajitha Lakshmi Podugu, Varaprasad Bodala, Kumari Yettula, Bharat Kumar Karasala, Siddaiah Vidavalur
Summary: An efficient and facile strategy for the synthesis of symmetrical pyridines has been developed, which provides good to excellent yields. In this strategy, ketoxime acetates and DMFDMA are reacted in the presence of FeCl3 catalyst at 120 degrees C for 6 hours under argon atmosphere. DMFDMA acts as an effective C1 synthon in this protocol. The advantages of this protocol include the use of inexpensive catalysts, no need for additional ligands and additives, and excellent functional group tolerance.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Multidisciplinary
Huan Yan, Gaochen Xu, Meng Gu, Sai Zhang, Qinghuan Wu, Jingjing Meng, Ning Zhu, Zheng Fang, Jindian Duan, Kai Guo
Summary: A novel synthesis method for trifluoromethyl-containing 2H-1,3-oxazines was developed by catalytically oxidizing alpha,beta-unsaturated ketoxime acetates with ethyl trifluoropyruvate. This procedure provides an alternative route towards functionalized 2H-1,3-oxazines.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Dong Cheng, Xiangzhen Meng, Shuailu Wang, Xuan Zhao, Jingwen Chen
Summary: A facile method for the synthesis of substituted pyridines has been developed by NH4I-catalyzed cycloaddition of oxime acetates and alkyl pyruvate. The reaction proceeds through N-O bond cleavage and C-C bond formation, and shows mild conditions and high functional group compatibility.
Article
Chemistry, Organic
Yu-Song Ran, Bo Jiang, Yun-Tao Shen, Tai-Gang Fan, Wei Jiang, Cui Zhang, Ya-Min Li
Summary: A visible-light-promoted cascade cyclization reaction has been developed for the synthesis of tetrahydrobenzo[mn]cyclopenta[b]acridines using 3-ethynyl-[1,1'-biphenyl]-2-carbonitriles and unsaturated alpha-bromocarbonyls. This reaction involves the formation of three C(sp(3))-C(sp(2)) bonds, one C(sp(2))-N bond, and three cycles in a single step, through the addition of a C-centered radical to the carbon-carbon triple bond and subsequent radical cyclizations. The reaction conditions are mild, and the reaction shows a wide substrate scope and high efficiency in bond formation.
Article
Chemistry, Physical
Pu-Fan Qian, Tao Zhou, Jun-Yi Li, Yi-Bo Zhou, Bing-Feng Shi
Summary: Chiral benzothiadiazine-1-oxides are sulfur-stereogenic compounds with structural diversity that have gained significant attention in drug discovery. This study reports the synthesis of these chiral molecules through an asymmetric [4 + 3] annulation reaction of sulfoximines with alpha,beta-unsaturated ketones, catalyzed by an achiral Ru(II) complex and assisted by a chiral carboxylic acid (CCA). The method allows for the preparation of a wide range of chiral benzothiadiazepine-1-oxides with various functional groups in high yields and excellent enantioselectivity, expanding the chemical space of chiral sulfoximines. Importantly, the oxidative cleavage of the products yields chiral N-benzoyl sulfoximines with a C-S chiral axis.
Article
Chemistry, Multidisciplinary
Takahiro Yamada, Yoshimitsu Hashimoto, Kosaku Tanaka, Nobuyoshi Morita, Osamu Tamura
Summary: An efficient method for the synthesis of multi-substituted pyridines with complete regioselectivity has been developed using Pd-catalyzed C-H activation. Mechanistic studies suggest that the pyridine products are formed by electrophilic C-H alkenylation of α,β-unsaturated oxime followed by electrocyclization. This method is more efficient than previously reported Rh-catalyzed strategies.
Article
Chemistry, Organic
Ashwini K. Nakate, Sagar S. Thorat, Shailja Jain, Gamidi Rama Krishna, Kumar Vanka, Ravindar Kontham
Summary: An unprecedented Ag(i)-catalyzed [3 + 3]-annulation of alkynyl alcohols and alpha,beta-unsaturated ketones is reported for constructing chromanes, featuring facile reaction conditions, broad substrate scope, and good to excellent yields. Experimental findings, supported by isolation of reaction intermediate and DFT calculations, corroborate the proposed mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Hai-Peng Li, Zhi-Neng You, Yuan-Yang Liu, Gao-Wei Zheng, Heng Gong, Yiming Mo, Ning Zhu, Yun-Peng Bai, Jian-He Xu
Summary: The use of a continuous-flow microreactor (CFMR) has significantly improved the efficiency of NAD(+)-dependent chenodeoxycholic acid oxidation, allowing for the production of high value-added chemicals. Compared to traditional batch reactions, the production yield increased by 96-fold, the total turnover number of NAD(+) improved by 10-fold, and enzyme consumption decreased by 7-fold.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Review
Chemistry, Multidisciplinary
Zhao Jin, Huiyue Wang, Xin Hu, Yihuan Liu, Yujing Hu, Shuangfei Zhao, Ning Zhu, Zheng Fang, Kai Guo
Summary: This review focuses on the impact of microreactor structure on anionic polymerization and its applications in polymer synthesis, providing guidance for flow chemistry and anionic polymerization.
REACTION CHEMISTRY & ENGINEERING
(2022)
Article
Engineering, Environmental
Kerui Chen, Wenjian Han, Xin Hu, Yihuan Liu, Yujing Hu, Shuangfei Zhao, Ning Zhu, Zheng Fang, Kai Guo
Summary: A microreactor-based enzymatic and metal-catalytic cascade reaction platform was developed for the synthesis of bottlebrush polymers. By using a continuous flow chemo-enzymatic strategy, well-defined bottlebrush polymers with fast kinetics and narrow molecular weight distribution were successfully prepared.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Polymer Science
Yi-Huan Liu, Xin Yuan, Jia-Qi Wu, Ming-Xuan Luo, Xin Hu, Ning Zhu, Kai Guo
Summary: The emerging chemical recyclable polymers provide a solution to plastic pollution, but their structures and properties are limited. In this study, a fully chemical recyclable copolymer P(GBL-co-((R)-M)) was reported, with tunable structures and properties achieved through controlling reaction conditions and catalyst. The copolymer shows potential for sustainable applications.
CHINESE JOURNAL OF POLYMER SCIENCE
(2022)
Article
Chemistry, Physical
Yifan Ding, Huan Wang, Yunyun Wang, Long Li, Jiahui Ding, Caiyan Yuan, Tao Xu, Haoran Xu, Hui Xie, Ning Zhu, Xin Hu, Huang Fang, Songwei Tan
Summary: This study developed a co-delivery system of luteolin and TGF-beta 1 gene for the treatment of intervertebral disc degeneration (IDD) using a polymer self-assembly technique. The results showed that this co-delivery system could inhibit inflammation, restore the balance of synthesis and catabolism, and delay the progression of IDD.
Article
Chemistry, Multidisciplinary
Shuzhan Wang, Tingting Shi, Zheng Fang, Chengkou Liu, Wei He, Ning Zhu, Yujing Hu, Xin Li, Kai Guo
Summary: A strategy integrating biotechnology and microtechnology was developed to enhance the optical purity of mandelic acids during kinetic resolution process. The study showed that the method achieved higher optical purity under optimal conditions and improved the kinetics properties.
JOURNAL OF FLOW CHEMISTRY
(2022)
Article
Electrochemistry
Jinze Du, Di Gao, Dong Zhang, Xinxin Lin, Chengkou Liu, Ning Zhu, Zhao Yang, Wei He, Zheng Fang, Kai Guo
Summary: This article presents a metal-catalyst-free and external-oxidant-free electrochemical oxidative radical C-H ortho-trifluoromethylation. The reaction specifically occurs at the ortho-position of anilides without directing groups. Various anilides show good tolerance and provide the desired products in moderate to good yields. Additionally, the gram-scale amplified product of benzanilide is obtained with a yield of 64%, demonstrating its potential for application.
Article
Engineering, Environmental
Xin Hu, Hui Zhang, Deqi Wu, Dongmei Yin, Ning Zhu, Kai Guo, Chunhua Lu
Summary: In this study, covalently bonded cross-linked inorganic-polymer nanocomposites were designed and prepared. By improving the dispersity of nanofillers in the matrix and forming a network structure, increased dielectric constant, suppressed dielectric loss, and elevated breakdown strength were achieved. The optimal sample exhibited an ultrahigh energy density, providing a potential alternative for the design of high-performance dielectric materials.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Engineering, Chemical
Shuangfei Zhao, Yingying Nie, Yimin Wei, Pengjie Yu, Wei He, Ning Zhu, Yuguang Li, Dong Ji, Kai Guo
Summary: The uniformity of mixing plays a crucial role in liquid-liquid two-phase chemical processes. This study proposes a specific surface area ratio to quantify the uniformity and designs a millimeter-scale mixer with a special baffle structure. By optimizing the baffle parameters, the specific surface area ratio and treatment capacity of the mixer are significantly improved.
INTERNATIONAL JOURNAL OF CHEMICAL REACTOR ENGINEERING
(2023)
Article
Engineering, Chemical
Yingying Nie, Shuangfei Zhao, Pengjie Yu, Yimin Wei, Runze Hu, Wei He, Ning Zhu, Yuguang Li, Dong Ji, Kai Guo
Summary: Due to scale effects, directly enlarging the size of the micromixer is an easy way to reduce the efficiency of mass and heat transfer in the continuous flow chemical process. A scale-up microfluidic mixer with a porous structure was designed to improve the mass and heat transfer efficiency. The effects of rotation angle, porosity, and baffle spacing were studied to optimize the mixer structure. Compared with the 1 mm mixer without structure, the scale-up mixer has a higher mixing efficiency and an 80% reduction in energy consumption at Re >= 700. The heat transfer efficiency of the mixer during fluid heating was evaluated using a Nusselt number. The results show that the porous baffle promotes the generation of secondary flow and enhances the heat transfer effect, making its Nu increase by three times compared with the unstructured mixer. The scale-up microfluidic mixer with a porous structure effectively improves the mass and heat transfer performance. This study can provide a reference for the design or development of a novel scale-up mixer.
CANADIAN JOURNAL OF CHEMICAL ENGINEERING
(2023)
Article
Chemistry, Applied
Huan Liang, Dongmei Yin, Lina Shi, Yihuan Liu, Xin Hu, Ning Zhu, Kai Guo
Summary: Functionalized cellulose has gained research interests for its potential in highly functional and environmentally friendly materials. Surface modification of cellulose via photo-induced click reaction integrates the advantages of photochemistry, click reaction, and surface modification. In this review, recent progress in cellulose surface modification using photo-induced click reactions is summarized. Different click reactions, such as thiol-X and cycloaddition reactions, are compared and their applications in cellulose modification are discussed. The challenges and outlook of photo-induced click reaction in cellulose surface modification are also addressed.
CARBOHYDRATE POLYMERS
(2023)
Article
Engineering, Environmental
Jiming Yang, Shulin Wang, Fudong Bai, Xingmei Lu, Wei He, Zheng Fang, Ning Zhu, Kai Guo
Summary: Pretreatment of lignocellulose with a binary system consisting of 1-n-butyl-3-methylimidazole chloride (BMIMCl) and arginine (Arg) at temperatures higher than the glass transition temperature of lignin (Tg-lignin) can effectively reduce cellulose crystallinity and lignin content, improving enzymatic hydrolysis efficiency and reducing enzyme dosage.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Thermodynamics
Pengjie Yu, Shuangfei Zhao, Yingying Nie, Yimin Wei, Runze Hu, Wei He, Ning Zhu, Yuguang Li, Dong Ji, Kai Guo
Summary: This study designed and optimized a novel mixer with triangular-notched rectangular baffles structure, and characterized its performance by combining heat and mass transfer computational fluid dynamics (CFD) method. The results showed that the optimized mixer had a significant increase in mixing efficiency and heat transfer compared to the mixer without baffles structure. Furthermore, the scale-up strategy for continuous flow chemical process enhancement was provided by enlarging the size of the mixer with triangular-notched rectangular baffles structures.
NUMERICAL HEAT TRANSFER PART A-APPLICATIONS
(2023)
Article
Polymer Science
Yihuan Liu, Guoqing Zuo, Han Gao, Zhao Wu, Wei Huang, Canliang Ma, Jie Yin, Xin Hu, Ning Zhu, Kai Guo
Summary: Poly(epsilon-caprolactone-co-epsilon-caprolactam) was successfully synthesized through ring-opening copolymerization and its thermal and mechanical properties were investigated. The results showed that the thermal properties of the polymer varied with the ester content, and the mechanical properties decreased with increasing epsilon-caprolactone incorporation.
POLYMER INTERNATIONAL
(2023)
Article
Chemistry, Multidisciplinary
Wei Lu, Ruijia Wang, Muqing Si, Yi Zhang, Shuangshuang Wu, Ning Zhu, Wenqin Wang, Tao Chen
Summary: In this study, robust fluorescent polymeric hydrogel actuators with spatially anisotropic structures were constructed using an interfacial supramolecular assembly (ISA) approach, enabling control over synergistic shape/color-changing behaviors. The proposed ISA approach is universal and expected to open new avenues for developing bioinspired intelligent soft actuators/robotics with selective spatial shape/color-changing behaviors.