Article
Chemistry, Multidisciplinary
Shivam A. A. Meena, Poonam Sharma, Akhilesh K. K. Verma
Summary: A transition-metal-free one-pot synthesis of di-functionalized succinimides has been developed, which involves a radical cascade seleno/thiosulfonation of aza-1,6-enynes in an atom economical manner. This method allows the synthesis of highly decorated succinimides with excellent stereoselectivity under mild reaction conditions. The proposed radical pathway is well supported by control experiments. The reaction demonstrates advantageous features including operational simplicity, atom economy, and broad substrate scope.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Organic
Zhenzhi Cai, Sven Trienes, Kairui Liu, Lutz Ackermann, Yan Zhang
Summary: During the past decade, photo- and electrochemical reactions via single-electron-transfer (SET) triggered radical pathways have been widely used to efficiently form chemical bonds. In particular, radical cyclization reactions of 1,n-enynes have been explored for the synthesis of bioactive compounds. This minireview summarizes recent progress in radical cascade cyclizations of 1,n-enynes (n = 5, 6, and 7) under photo/electrochemical conditions until September 2023, providing a categorized overview and understanding for readers.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Lin-Ping Hu, De-Run Zhang, Xiao-Hong Huang, Feng-Lin Liu, Xia Li, Ming-Yu Teng, Guo-Li Huang
Summary: The method involves the aryl sulfonyl radical-triggered cascade cyclization of phenyl-linked 1,6-enynes to synthesize biologically important indenes containing alkenyl C-X bonds and 10a,11-dihydro-10H-benzo[b]fluorines. Three new chemical bonds, including C-S, C-C, and C-X bonds, and three C-C bonds are formed in one step. The metal-free, mild reaction conditions, broad substrate scope, and good functional group tolerance make the method attractive and valuable.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
You-lu Pan, Xiao-meng Gong, Rong-rong Hao, Shen-xin Zeng, Zheng-rong Shen, Wen-hai Huang
Summary: A facile CuBr2 induced radical relay addition/cyclization reaction has been developed for the synthesis of a broad range of sulfonated compounds. Some of the synthesized compounds exhibited bioactivity against cancer cell lines. This protocol offers advantages of low-cost, base-free, simple operation, and broad functional group tolerance.
Article
Biochemistry & Molecular Biology
Hongqiang Dong, Chunli Chen, Jinlei Zhao, Yigang Ji, Wenchao Yang
Summary: The focus of this investigation is a novel approach to synthesize sulfonylated heterocycles, which addresses the limitations of conventional methods by using an affordable sulfonylating agent and operating under metal-free and photocatalyst-free conditions.
Article
Chemistry, Multidisciplinary
Xuan Huang, Huichao You, Fang Fang, Fan Wang, Zhong-Quan Liu
Summary: This study demonstrated an efficient and selective radical nitration of olefins with NaNO2, leading to the synthesis of various (E)-nitroolefins in high yields.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Han Wang, Yongbin Xie, Yicheng Zhou, Nannan Cen, Wenbo Chen
Summary: A new electrochemical strategy for trifluoromethylation/cyclization using TfNHNHBoc as a CF3 source has been developed. This approach involves the direct electrolysis of TfNHNHBoc under external oxidant-free and catalyst-free conditions, leading to the formation of various trifluoromethylated oxindoles with good functional group compatibility and broad substrate scope.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Zhi-Wei Zhao, Yu-Song Ran, Yu-Jian Hou, Xin Chen, Xue-Ling Ding, Cui Zhang, Ya-Min Li
Summary: Free radical carbochloromethylation reactions of ortho-cyanoarylacrylamides and N-(arylsulfonyl)acrylamides have been developed using simple alkyl chlorides as the chloromethyl source. These transformations exhibit wide functional group compatibility and provide efficient methods for constructing polychloromethyl-substituted quinoline-2,4-diones and alpha-aryl-beta-polychloromethylated amides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mingming Yu, Tiantian Huang, Lin Zhang, Muhammad Shabbir, Yuhan Gao, Yi-Hung Chen, Hong Yi, Aiwen Lei
Summary: An efficient electrochemical strategy for the synthesis of selenated and trifluoromethylated dihydropyran compounds is reported in this study. The reaction proceeds smoothly under mild electrolysis conditions and exhibits a broad substrate scope and scalable synthesis potential.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Organic
Changjun Zhang, Zhichen Yu, Yuxin Ding, Yuan Shi, Yuanyuan Xie
Summary: This study describes an eco-friendly approach for electrochemistry-mediated radical cascade cyclization of N-methacryloyl-2-phenylbenzoimidazoles using CF3SO2Na as the CF3 radical source. The reaction exhibits mild reaction conditions, readily available substrates, and moderate to good yields through the construction of two C-C bonds in one step.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Organic
Jianhua Liao, Xiao Yang, Lu Ouyang, Yinlong Lai, Jiuzhong Huang, Renshi Luo
Summary: Cascade radical cyclization is an attractive synthetic method with high atom- and step-economy for constructing carbo- and heterocycles, playing key role in chemical and life science industries. The latest achievements in the development of cascade radical cyclization methodologies in this growing research field are highlighted, including various bond couplings and representative examples discussed for future research tools.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Shangyuan Wang, Jiangjie Zhang, Jian-Shu Wang, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed cascade radical cyclization and carbonylation reaction of 1,7-enynes with perfluoroalkyl iodides and alcohols has been developed. The use of benzene-1,3,5-triyl triformate (TFBen) as the CO source enables the construction of 3,4-dihydroquinolin-2(1H)-one skeletons with the incorporation of both perfluoroalkyl and carbonyl units. This method provides a facile and efficient approach for the synthesis of various 3,4-dihydroquinolin-2(1H)-one derivatives with moderate to high yields and excellent E/Z selectivity.
Article
Chemistry, Applied
Chada Raji Reddy, Roshan Chandrakant Kajare, Nagender Punna
Summary: Herein, we report the synthesis of functionalized dihydro-benzo[b]fluorenones through a manganese-mediated cascade radical cyclization method. The method features high atom- and step-economy, and allows for the construction of three new C-C bonds with high yields under mild reaction conditions, demonstrating the synthetic efficacy of the developed method.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Chunxiang Pan, Gaowei Wang, Hengyuan Zhao, Jianxiao Ni, Ruifeng Fan, Yongyun Zhou, Yuanbin Zhu, Shiyuan Wu, Baomin Fan
Summary: An efficient stereoselective cobalt-catalyzed hydrovinylative cyclization of 1,6-enynes with chalcones to obtain functionalized pyrrolidines has been developed. The products were furnished in good yields with up to 93% ee. A plausible mechanism through which the transformation was initiated by cyclization of 1,6-enynes is proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Wan-Qiang Yuan, Yu-Tao Liu, Yu-Qing Ni, Yong-Ze Liu, Fei Pan
Summary: An efficient and transition-metal-free photocatalytic trifluoromethylation-gem-difluoroallylation reaction of unactivated alkenes has been developed. This protocol utilizes manageable Langlois' reagent as the CF3 radical source and alpha-trifluoromethyl alkene as the gem-difluoroalkenyl source in the presence of Fukuzumi acridinium salts as a photocatalyst. The reaction proceeds under mild conditions and provides diverse trifluoromethyl-substituted gem-difluoroalkenes in moderate to good yields.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Organic
Wu Jintao, Liu Zhongquan
Summary: This article summarizes the research progress on effective functionalization of inert C(sp(3))-C(sp(3)) bond from the perspective of free-radical chemistry, and demonstrates the progresses and corresponding mechanisms for free-radical promoted selective cleavage of saturated C-C bonds in alcohols and ethers, amines, aryl alkanes and simple alkancz according to the initiating manners such as thermochemistry, photochemistry and electrochemistry.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Engineering, Electrical & Electronic
Fan Wei, Guanghua Xu, Qingqiang Wu, Jiachen Kuang, Peiyuan Tian, Penglin Qin, Zejiang Li
Summary: The article compares the hardware parameters of different Kinect third-generation products, calibrates the RGB camera and IR camera of Azure Kinect, evaluates the shooting accuracy of the depth camera, and provides parameter optimization suggestions.
IEEE SENSORS JOURNAL
(2022)
Article
Chemistry, Applied
Zhihui Sun, Ruixue Ji, Jintao Wu, Jianyou Zhao, Fang Fang, Fan Wang, Chao Jiang, Zhong-Quan Liu
Summary: We present a modified Clemmensen reduction in which aliphatic and aromatic aldehydes and ketones undergo deoxygenative hydrogenation and deuterization to form hydrocarbons and deuterocarbons when reacted with aqueous H(D)Cl in an undivided cell. This method has several notable features: 1) H+/D+ as the sources of H/D; 2) mild reaction conditions (room temperature, open flask, CH3CN and water as cosolvent); 3) easily scaled-up to 100 grams. A series of D-labeled drugs were successfully synthesized using this approach.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Zhihong Qiu, Xianting Huang, Jintao Wu, Zhong-Quan Liu
Summary: An electrochemical methodology for the reductive alkylation, allylation, and propargylation of quinoxalin-2(1H)-ones with haloalkanes was reported herein. Using an undivided cell and constant current, a wide range of 3-alkylated-3,4-dihydroquinoxalin-2(1H)-one and its derivatives could be obtained in yields of 25-87%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Shiliu Chen, Qinqin Yan, Jie Fan, Changyou Guo, Lijun Li, Zhong-Quan Liu, Zejiang Li
Summary: A photo-promoted mild tandem 6-exo-trig spirocyclization method has been developed to synthesize thiocyanate-containing spiro[5,5]trienones with high yields and regioselectivity. Additionally, other thiocyanate-substituted cycles can also be produced under similar conditions. The merits and reaction mechanism of this radical system were investigated through scaled-up operations, functional group transformations, intermediate capture study, and on/off light experiments.
Article
Chemistry, Organic
Yunfei Tian, Luping Zheng, Zhiqiang Wang, Zejiang Li, Weijun Fu
Summary: A new strategy of electrochemical oxidative difluoroethylation using sodium difluoroethylsulfinate (DFES-Na) has been reported for generating difluoroethyl radical. This method provides a quick access to valuable difluoroethylated azaheterocycles including oxindoles and isoquinoline-1,3-diones via radical tandem difluoroethylation/cyclization with moderate to good yields. The electrochemical cyclopropyldifluoromethylation of N-arylacrylamides also showed good results using this strategy. Furthermore, radical capture and cyclic voltammetry (CV) experiments were conducted to determine the proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Yunfei Tian, Luping Zheng, Yuting Yang, Jiayi Liu, Zihan Jing, Zejiang Li, Weijun Fu
Summary: An electrochemical oxydifluoroethylation of alkenes using the anodic oxidative generation of MeCF2 radical has been achieved, resulting in the synthesis of diversified difluoroethylated benzoxazines and lactones in yields of 35-87%. The method was also extended to the synthesis of cyclopropyldifluoromethylated benzoxazines. Mechanistic studies revealed that the reaction proceeded via a radical process involving tandem C-CF2R and C-O bond formation.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Yang Li, Lijun Li, Changyou Guo, Qinqin Yan, Hongxun Zhou, Ying Wang, Zhong-Quan Liu, Zejiang Li
Summary: A metal/peroxide-free cascade reaction involving the 6exo-trig spirocyclization of tert-butyl nitrite with biaryl ynones has been successfully accomplished, leading to various NO2-modified spiro[5,5]trienones with high regioselectivity and yields. Scaled-up experiments, reduction/epoxidation operations, and mechanistic studies were conducted to confirm the advantages and spirocyclization process of this radical system. The structure of the spirocycles was ultimately confirmed by single-crystal X-ray diffraction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Yunfei Tian, Luping Zheng, Ying Chen, Yufei Li, Mengna Wang, Weijun Fu, Zejiang Li
Summary: The direct oxidative alkenylation of indoles using ferrous salts under mild conditions provides an effective one-step synthesis of 3-alkylideneindolin-2-one. This reaction system is characterized by simple and readily available materials, mild conditions, and easy accessibility. Control experiments indicate the involvement of a radical pathway in the reaction. Furthermore, the method shows good performance in gram-scale experiments, highlighting its broad potential in synthetic chemistry.
Article
Chemistry, Organic
Changyou Guo, Lijun Li, Qinqin Yan, Hongxun Zhou, Zhong-Quan Liu, Zejiang Li
Summary: A photopromoted cyanomethylation/cyclization reaction of aryl acetylenes/ethylenes with bromoacetonitrile was developed, providing an efficient and mild protocol for the synthesis of cyanomethylated 7- or 5-membered N-heterocycles in good yields. Trichloroacetonitrile was also compatible with this radical pathway. The tandem system exhibited excellent performance in various aspects, including single-crystal X-ray diffraction measurements, scaled-up operations, functional group transformations, light on/off experiments, and radial inhibition studies.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Engineering, Biomedical
Qingqiang Wu, Penglin Qin, Jiachen Kuang, Fan Wei, Zejiang Li, Ruping Bian, Chengcheng Han, Guanghua Xu
Summary: Early diagnosis of infant cerebral palsy (CP) is crucial for the health of infants. This paper presents a novel training-free method for quantifying infant spontaneous movements to predict CP.
IEEE TRANSACTIONS ON NEURAL SYSTEMS AND REHABILITATION ENGINEERING
(2023)
Article
Chemistry, Organic
Yunfei Tian, Luping Zheng, Zhiqiang Wang, Zejiang Li, Weijun Fu
Summary: A new strategy for electrochemical oxidative difluoroethylation using sodium difluoroethylsulfinate (DFES-Na) has been reported, which successfully generates difluoroethyl radical for the first time. This method allows the quick synthesis of valuable difluoroethylated azaheterocycles, including oxindoles and isoquinoline-1,3-diones, in moderate to good yields. The electrochemical cyclopropyldifluoromethylation of N-arylacrylamides also shows good results using this strategy. Furthermore, radical capture and cyclic voltammetry (CV) experiments were carried out to confirm the proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xuan Huang, Huichao You, Fang Fang, Fan Wang, Zhong-Quan Liu
Summary: This study demonstrated an efficient and selective radical nitration of olefins with NaNO2, leading to the synthesis of various (E)-nitroolefins in high yields.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Shiliu Chen, Qinqin Yan, Jie Fan, Yongjun Gao, Xiulong Yang, Lijun Li, Zhongquan Liu, Zejiang Li
Summary: Photoinduced radical cascade cyclization of aryl acetylenes with NH4SCN provides a simple and mild protocol for the synthesis of SCN-containing dibenzazepines or dioxodibenzothiazepines. Various scaled-up operations, functional group transformations, radical capture studies, and on/off light experiments were performed to test the merits of the desired products and the reaction process.
Review
Chemistry, Organic
Xiaojie Shang, Zhong-Quan Liu
Summary: This review summarizes the advances in utilizing organoboronic acids as carbon-centered radical precursors for constructing diverse C-C bonds. The content is divided into four parts based on the different categories of coupling partners with organoboronic acids. The reaction conditions and mechanisms are demonstrated in each part.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
