Article
Chemistry, Organic
Fu-Sheng He, Lingjing Su, Feiyan Yu, Zhimei Tang, Jie Wu
Summary: An iron-catalyzed method for dearomative spirocyclization of biaryl ynones using sodium metabisulfite and cycloketone oxime esters has been developed. This approach allows for the rapid synthesis of sulfonated spiro[5,5]trienones with a wide substrate scope and good functional group tolerance. Mechanistic studies reveal the generation of cyanoalkyl and cyanoalkylsulfonyl radicals during the reaction process.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jin-Wei Yuan, Lu Shen, Meng-Yao Ma, Shi Feng, Wan Yang, Liang-Ru Yang, Yong-Mei Xiao, Shou-Ren Zhang, Ling-Bo Qu
Summary: A visible-light-catalyzed difluoroacetylated spirocyclization reaction of N-arylpropiolamides with ethyl bromodifluoroacetate as a CF2CO2Et radical precursor is described. This approach enables the formation of two carbon-carbon bonds and one carbon-oxygen bond in a single reaction through a sequence of C-H oxidative coupling, ipso-cyclization, and dearomatization processes, providing a straightforward route to synthesize CF2CO2Et-containing spiro[4.5]trienones in moderate to good yields.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Applied
Wen-Chao Yang, Liu-Yu Shen, Jun-Nan Li, Jian-Guo Feng, Pinhua Li
Summary: A K2S2O8-promoted nitration/spirocyclization reaction of biaryl ynones using inexpensive NaNO2 as the nitro source has been reported. This cascade reaction involves the nitration of alkynes followed by 6-exo-trig spirocyclization and dearomatization, resulting in the formation of NO2-containing spiro[5.5]trienones in yields of 63-85%. Furthermore, the reaction provides a practical method for the synthesis of nitrated indenones and thioflavones with yields of 58-85%.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Jun-Nan Li, Zi-Jie Li, Liu-Yu Shen, Pinhua Li, Yicheng Zhang, Wen-Chao Yang
Summary: A selective polychloromethylation and halogenation reaction of alkynes was disclosed using a radical addition/spirocyclization cascade sequence. By utilizing polyhaloalkanes as precursors for polyhalomethyl and halogen radicals, a series of valuable spiro[5,5]trienones containing halogen-, CHCl2-, or CCl3-groups were synthesized in good yields under simple and mild conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Applied
Fei Chen, Yang Zheng, Hao Yang, Qing-Yun Yang, Lu-Yan Wu, Nengneng Zhou
Summary: In this study, an iron-catalyzed cascade reaction was developed for the synthesis of silylated spiro[5.5]trienones using silane as the precursor of silyl radical. The approach involved 1,10-phenanthroline as the ligand and tert-butyl hydroperoxide (TBHP) as the oxidant, leading to the formation of silylated compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Ke Yu, Xianqiang Kong, Jiajun Yang, Guodong Li, Bo Xu, Qianjin Chen
Summary: A green method for synthesizing spiro[4.5]trienones through electrochemical oxidative halocyclization with N-aryl alkynamides was developed without the need for metal catalysts or external oxidants. Using LiCl, LiBr, and LiI as halogen sources, a variety of dearomative halo-spirocyclization products were obtained in good to excellent yields with a broad scope and functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Liu-Yu Shen, Yu Sun, Yu-Qi Wang, Bing Li, Wen-Chao Yang, Peng Dai
Summary: A direct and efficient strategy for the trifluoromethylthiolation and dearomatization of biaryl ynones with stable and readily available AgSCF3 has been developed. The reaction occurs smoothly in the presence of K2S2O8 via a 6-exo-trig radical cyclization, providing a variety of SCF3-containing spiro [5,5] trienones in good yields.
Article
Chemistry, Organic
Wen-Chao Yang, Ming-Ming Zhang, Yu Sun, Cai-Yun Chen, Lei Wang
Summary: A novel and efficient strategy has been developed for trifluoromethylthiolation and dearomatization of activated alkynes using stable and readily available AgSCF3. The unprecedented electrochemical generation of the SCF3 radical enables the synthesis of SCF3-containing spiro[5,5]trienones in good yields via a 6-exo-trig radical cyclization.
Article
Chemistry, Organic
Zhichao Chen, Xinran Zheng, Shu-Feng Zhou, Xiuling Cui
Summary: This study explores a visible-light induced dearomative cascade cyclization of biaryl ynones with diselenides under photocatalyst and external additive-free conditions, yielding a series of selenated spiro[5.5]trienones in moderate to good yields. It is found that the Se-Se bond in diselenides can be cleaved to generate arylselenyl radicals under visible light irradiation without the need for a photocatalyst. The developed protocol provides a facile and green method for the synthesis of spiro[5.5]trienones.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Dong Xia, Xin-Fang Duan
Summary: The study presents an unprecedented dearomatization of biaryl ynones with aldehydes via double C-H functionalization, where regiospecific remote unactivated para-C-H functionalization efficiently furnishes acylated spiro[5.5]trienones, demonstrating high efficiency and economy.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Pu Chen, Jian-Hong Fan, Wen-Qin Yu, Bi-Quan Xiong, Yu Liu, Ke-Wen Tang, Jun Xie
Summary: A method for the preparation of 3-alkylated spiro[4.5]trienones via alkylation/ipso-cyclization reaction of activated alkynes with 4-alkyl-DHPs under transition-metal-free conditions is proposed. The mechanism studies indicate that the alkylation/ipso-cyclization reaction involves radical processes. This ipso-cyclization procedure offers a series of advantages, including accessibility, mild conditions, high efficiency, greater safety, and environmental friendliness.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kangdong Mo, Xiaocong Zhou, Ju Wu, Yufen Zhao
Summary: A robust dearomative denitration method has been developed through a radical ipso-cyclization process, leading to the synthesis of valuable phosphonated or trifluoromethylated azaspiro[4.5]trienones with good functional group tolerance. This approach represents a convenient and powerful way to activate nitroarenes in a radical manner.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Chada Raji Reddy, Dattahari H. Kolgave, Uprety Ajaykumar, Remya Ramesh
Summary: A copper-catalyzed ipso-annulation reaction of N-(p-methoxyaryl)propiolamides with 1,3-diketones has been developed, enabling the synthesis of diketoalkylated spiro[4.5]trienones and spiro[5.5]trienones.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Man Yang, Jiawei Hua, Hao Wang, Tao Ma, Chengkou Liu, Wei He, Ning Zhu, Yujing Hu, Zheng Fang, Kai Guo
Summary: A metal-and oxidant-free pathway for the synthesis of azaspiro[4.5]decane-6,9-dione via photomediated iodinated spirocyclization has been developed. The reaction proceeds through a radical addition/ipso-cyclization/dearomatization process at room temperature, leading to the formation of C-C and C-I bonds. This green and convenient approach can be applied to the synthesis of various iodinated spirocyclization products in moderate to good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Man Yang, Jiawei Hua, Hao Wang, Tao Ma, Chengkou Liu, Wei He, Ning Zhu, Yujing Hu, Zheng Fang, Kai Guo
Summary: A metal- and oxidant-free reaction route has been developed for the synthesis of azaspiro[4.5]deca-6,9-diene-3,8-dione via photomediated spirocyclization of N-(4-methoxybenzyl) propiolamide. The reaction involves radical addition/ipsocyclization/dearomatization processes and successfully forms C-C and C-I bonds. This green and convenient approach can be widely used to produce a variety of iodinated spirocyclization products in moderate to good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Analytical
Xiurong Zhai, Shuai Li, Yukun Wang, Siyu Cao, Wen Sun, Mingzhu Liu, Guojiang Mao, Bingqiang Cao, Hua Wang
Summary: A magnet-renewable electroanalytical strategy has been developed for monitoring hydrogen sulfide (H2S) in aquaculture freshwater systems using magnetic Fe3O4-loaded silver metal-organic framework (Fe3O4@Ag-MOF). The method exhibits sensitive and stable signals with rational signal decline in the presence of H2S. The electrodes can be easily renewed for immobilization of Fe3O4@Ag-MOF probes, facilitating detection in aquaculture freshwater samples.
ANALYTICA CHIMICA ACTA
(2022)
Article
Chemistry, Analytical
Chunxian Zhang, Shuai Li, Zhiqiang Duan, Qin Li, Mengxuan Zhao, Yulong Chen, Xiurong Zhai, Guojiang Mao, Hua Wang
Summary: Water-soluble non-conjugated polymer dots were synthesized using hyperbranched polyethyleneimine and dihydroxybenzaldehyde for the first time. These polymer dots exhibited strong green fluorescence in aqueous media and could be quenched by MnO2 nanosheets and restored by thiocholine. A highly selective fluorimetric method for detecting organophosphorus pesticides was developed based on these characteristics.
ANALYTICA CHIMICA ACTA
(2022)
Article
Engineering, Environmental
Zongzhao Sun, Haozhe Dong, Qi Yuan, Yueyang Tan, Wu Wang, Yabin Jiang, Jianyong Wan, Jiangwei Wen, Jianjing Yang, Jiaqing He, Tao Cheng, Limin Huang
Summary: Self-supported hierarchical crystalline carbon nitride arrays (MA-rod array) with an omasum-like architecture were synthesized through molten salt-assisted pyrolysis. The MA-rod array showed excellent properties in photocatalytic hydrogen evolution and oxidative organic synthesis. It exhibited significantly higher hydrogen production rate and a high apparent quantum yield in photoredox catalysis compared to other photocatalysts.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Organic
Kelu Yan, Xiao Liu, Min Liu, Jiangwei Wen, Mingyue Du, Yingxue Fu, Wenxin Chen
Summary: The iridium-catalyzed oxidative coupling and cyclization of NH isoquinolones with olefins have been successfully achieved, resulting in the synthesis of various isoindolo[2,1-b]isoquinolin-5(7H)-one derivatives in moderate to good yields. Furthermore, several derivatization reactions, including functional group conversion and C-H/olefin coupling, were also performed. This study is of great importance for the further development of Cp*Ir(III) catalyzed coupling and cyclization reactions of NH substrates with olefins.
TETRAHEDRON LETTERS
(2022)
Article
Multidisciplinary Sciences
Cong Niu, Jianjing Yang, Kelu Yan, Jiafang Xie, Wei Jiang, Bingwen Li, Jiangwei Wen
Summary: A straightforward and practical strategy for pyridylation of inert N-heterocycles, enabled by ammonium cation and electrochemical, has been described. This protocol allows for the synthesis of various N-fused heterocycles and bidentate nitrogen ligand compounds without the need for exogenous metal and redox reagents. The reaction shows broad substrate scope, high functional group tolerance, and can be easily scaled up. Experimental and theoretical results support the proposed mechanism, and the resulting product can be used for fluorescence recognition of Fe2+ and Pd2+ with high sensitivity.
Article
Chemistry, Applied
Jianjing Yang, Xue Sun, Kelu Yan, Hongzhao Sun, Shuai Sun, Xiaoyu Jia, Fanjun Zhang, Jiangwei Wen
Summary: A metal- and exogenous-oxidant-free oxidation-induced oxyphosphorylation method for the synthesis of beta-ketophosphonates from alkenes and alkynes using water has been developed under electrochemical conditions. The protocol is compatible with a wide range of substrates and allows for gramscale synthesis of the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Analytical
Luping Feng, Lixiang Zhang, Su Chu, Sheng Zhang, Xi Chen, Yushuang Gong, Zhongling Du, Guojiang Mao, Hua Wang
Summary: A nanozyme with a 2D/1D heterostructure, SWCNTs@MoS2, was successfully fabricated and demonstrated improved peroxidase-like catalysis, along with selective detection of glutathione (GSH). A colorimetric method based on SWCNTs@MoS2 was proposed for quantitative analysis of GSH, showing potential for extensive applications in clinical laboratory settings. This study opens up possibilities for designing various nanozymes with enhanced catalytic activity.
ANALYTICA CHIMICA ACTA
(2022)
Article
Chemistry, Organic
Jing Ma, Jianjing Yang, Kelu Yan, Bingwen Li, Boju Luo, Meirou Jing, Yumeng Zhou, Ziling Wu, Laijin Tian, Jiangwei Wen
Summary: This study successfully achieved the site-selective hydropyridylation of ynones by manipulating electron transfer. Mechanistic investigations revealed the importance of solvation and protonation reagents, and identified the rate determining step of ynones hydrogenation on the cathode surface.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Analytical
Chenchen Xu, Qingqing Liu, Su Chu, Pan Li, Fengxiang Wang, Yanmei Si, Guojiang Mao, Choufei Wu, Hua Wang
Summary: A microdots array-based fluoremetric method with superwettability profile was developed for simultaneous and separate detection of Fe3+ and Cu2+ ions in red wine samples. The fluoremetric microdots array platform was obtained by designing a wettable micropores array and immobilizing fluorescent probes in it. The platform enabled the accumulation of targeting ions without tedious preprocessing and reduced cross-contamination. The feasibility of simultaneous and separate detection of Fe3+ and Cu2+ ions in red wine samples was demonstrated.
ANALYTICA CHIMICA ACTA
(2023)
Article
Chemistry, Multidisciplinary
Jiangwei Wen, Ting Zeng, Kelu Yan, Lulu Zhao, Shuyun Zhu, Jianjing Yang
Summary: A novel, straightforward, and scalable base-mediated one-pot three-component desulphurization cross-coupling strategy is reported for the synthesis of 4-cyanoimidazole derivatives. Over 35 examples are provided and achieved yields exceeding 85%. Notably, the majority of these readily available compounds can be isolated through simple filtration, thereby circumventing the need for laborious column chromatography.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Ting Zeng, Jianjing Yang, Kelu Yan, Wei Wei, Jiangwei Wen
Summary: This study developed a consecutively paired electrolytic-mediated controllable radical cross-coupling method for thiophenols with dichloromethane to deliver dithioacetals, sulfides, and sulfoxides in the absence of electrochemical mediator conditions. It features a wide substrate scope, simple operation, gram-scale synthesis, and eco-friendly characteristics.
GREEN SYNTHESIS AND CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Xiaoyu Wang, Kelu Yan, Jiangwei Wen, Qiuyun Li, Ke Ma, Wenlu Zhang, Wanhua Sun, Jianjing Yang
Summary: A DBU-promoted three-component cascade annulation has been proposed for the synthesis of tetrasubstituted selenophenes. This method offers advantages such as readily available and inexpensive substrates, metal catalyst-free reaction conditions, and high atom economy.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Bingwen Li, Hongyun Qin, Kelu Yan, Jing Ma, Jianjing Yang, Jiangwei Wen
Summary: A metal-free method for the synthesis of symmetrical and unsymmetrical 3,3'-DIMs through electrolytic C-H alkylation of indoles has been reported. The method utilizes N-hydroxyphthalimide as a catalyst and water as the solvent, without any metal contamination.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Ting Zeng, Jianjing Yang, Kelu Yan, Shibo Wang, Shuyun Zhu, Xian-En Zhao, Dandan Li, Jiangwei Wen
Summary: A metal-free, operationally simple, and scalable electrooxidation method was reported for the selective cleavage of C-N bonds of tertiary amines, providing access to asymmetric thiourea, selenourea, and 2-aminated benzoselenazole derivatives. Over 50 examples were reported with yields greater than 96%. The readily accessible compounds 10c and 24c showed promising anticancer activity against mouse breast cancer and human lung adenocarcinoma cancer cell lines (A549), highlighting the importance of this methodology.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Analytical
Yuchun Qiao, Yu Fang, Jizhen Shang, Xiaoting Zhao, Shuai Li, Guojiang Mao, Hua Wang
Summary: In this study, a fluorescent test strip with suppressed CRE of silver nanocluster probes coated by gelatin was successfully fabricated using vacuum-aided fast lyophilization, enabling uniform and stable probe deposition as well as sensitive quantitative analysis.
