Default Latest Most Read Please wait a minute... Reviews Recent Advances of Phosphorus-Centered Radical Promoted Difunctionalization of Unsaturated Carbon-Carbon Bonds Gao Yuzhen, Tang Guo, Zhao Yufen Chin. J. Org. Chem. 2018, 38 (1): 62-74. DOI: 10.6023/cjoc201708023 Published: 08 September 2017 Abstract (1512) PDF (839KB)(2426) Knowledge map The scientists have been working on developing more efficient and green ways to synthesize organophosphorus compounds as they have broad utilities such as reagents for chemical reactions, photovoltaic materials, flame retardants, biologically active molecules and so on. The difunctionalization reactions between P-center radicals and unsaturated compounds provide powerful methods for the synthesis of organophosphorus compounds in least and concise steps. This review will summarize the recent development in this area on the basis of different types of P-centered radical initiators. Reference | Related Articles | Metrics Cited: CSCD(1) Articles Copper-Catalyzed Decarboxylative Coupling of Alkenyl Acids with P(O)H Compounds at Room Temperature Qiao Huijie, Sun Suyan, Kang Jianxun, Yang Fan, Wu Yusheng, Wu Yangjie Chin. J. Org. Chem. 2018, 38 (1): 86-94. DOI: 10.6023/cjoc201708049 Published: 26 September 2017 Abstract (595) PDF (524KB)(830) Knowledge map A simple and mild protocol for the copper-catalyzed decarboxylative coupling of alkenyl acids with P(O)H compounds was developed, thus providing a facile route to the vinylphosphorus compounds. Moreover, the reaction could also afford β-ketophosphorus compounds as the major products in air using oxygen as an oxidant. In addition, the remarkable features of these two types of reactions include excellent reaction chemoselectivity, good functional group tolerance and mild reaction conditions (e.g., cheap oxidant, ligand-free condition and room temperature). Reference | Supporting Info. | Related Articles | Metrics Articles I2/CuI-Mediated Oxidative Cyclization of Enamides to Polysubstituted Oxazoles Yu Wenquan, Chang Junbiao Chin. J. Org. Chem. 2018, 38 (1): 215-220. DOI: 10.6023/cjoc201708009 Published: 15 September 2017 Abstract (814) PDF (485KB)(636) Knowledge map A concise and efficient iodine/copper(I) iodide-mediated intramolecular oxidative C—O bond formation reaction has been developed for oxazole synthesis. Under the optimal reaction conditions, oxidative cyclization of readily accessible enamide substrates provides facile access to a variety of oxazole derivatives bearing aryl, alkyl, amide, ester, and acyl substituents. Reference | Supporting Info. | Related Articles | Metrics Cited: CSCD(2) Reviews Research Progress of Asymmetric Synthesis of Optically Active P-Stereogenic Organophosphoryl Compounds by Chiral Induction Liu Shuang, Li Yuming, Wang Dian, Wei Rong, Miao Zhiwei Chin. J. Org. Chem. 2018, 38 (2): 341-349. DOI: 10.6023/cjoc201708040 Published: 16 October 2017 Abstract (992) PDF (594KB)(1756) Knowledge map Organo-phosphorus chemistry is an important branch of organic chemistry and life science research. P-Stereogenic organophosphorus compounds have attracted great interest due to their potential applications in the fields of pharmaceutical chemistry, agrochemistry, material science and as ligands for asymmetric catalysis. The preparation of enantiomerically enriched phosphorus compounds with P-stereogenic centers using natural chiral compounds as chiral auxiliary has received considerable attention. The recent development of the asymmetric synthesis of P-stereogenic organophosphoryl compounds employing menthol, sparteine, ephedrine, and carbohydrates as chiral auxiliary is summarized. Reference | Related Articles | Metrics Cited: CSCD(1) Reviews Progress of Fluorescent Bio-probe Based on Water-Soluble Boron-dipyrromethene Lu Bowei, Meng Shuxian, Feng Yaqing Chin. J. Org. Chem. 2018, 38 (2): 350-362. DOI: 10.6023/cjoc201706018 Published: 11 October 2017 Abstract (1132) PDF (829KB)(1631) Knowledge map Recently, the fluorescent bio-probe based on water-soluble boron-dipyrromethene (BODIPY) obtains enormous progress on structural optimization and functional modification, and becomes novel high-performance biological imaging materials owing to the development of hydrophilic modification. Focusing on the methods for improving the hydrophilicity of BODIPY, the water-soluble BODIPYs have been classified as ionic probe, electrically-neutral probe and amphiphilic probe. The research progress on the application of water-soluble BODIPY dyes in field of biology and medicine since 2006 has been summarized in this review, such as detection of necessary and pathogenicbiological chemical components, early detection and intervention of cancer, labelling drug delivery, marking specific organelles, real-time monitoring of biochemical and property changes with cells, andphotodynamic therapy. The merits of methods for improving the hydrophilicity and main issues of current studies have been summed up. The hypothesis for future directions has also been put forward. Reference | Related Articles | Metrics Cited: CSCD(1) Articles Triphenylphosphine Mediated Direct Trifluoromethylthiolation of Indolizine and Pyrrole by Trifluoromethanesulfonyl Chloride Zhao Xia, Li Tianjiao, Tian Miaomiao, Su Zhiyang, Wei Aoqi, Lu Kui Chin. J. Org. Chem. 2018, 38 (3): 677-683. DOI: 10.6023/cjoc201706038 Published: 15 November 2017 Abstract (615) PDF (495KB)(570) Knowledge map A triphenylphosphine mediated direct trifluoromethylthiolation of indolizine and pyrrole by trifluoromethanesulfonyl chloride was developed. The readily accessable reagents and transition metal-free reaction conditions allowed this protocol applicable for large scales synthesis. Reference | Supporting Info. | Related Articles | Metrics Cited: CSCD(1) Articles Metal-Free Oxidation of Thiols by N-Fluorobenzenesulfonimide: A Rapid and Efficient Method to Synthesize Disulfides Jing Lia, Jin Huia, Guan Meib, Wu Xiaohuaa, Wang Qiantaoa, Wu Yonga Chin. J. Org. Chem. 2018, 38 (3): 692-697. DOI: 10.6023/cjoc201709039 Published: 15 November 2017 Abstract (726) PDF (437KB)(826) Knowledge map A simple and rapid method is developed for the oxidation of thiols to the corresponding disulfides using N-fluorobenzenesulfonimide (NFSI) as the oxidant without any contamination by over oxidation. The synthetic protocol for disulfide bond formation proceeded efficiently under external base-and metal-free conditions with the advantages of simple operation, mild reaction conditions as well as short reaction times. Reference | Supporting Info. | Related Articles | Metrics Reviews Research Progress towards Synthesis of Aryl Boronic Acid Compounds Xu Yuliang, Fang Hao Chin. J. Org. Chem. 2018, 38 (4): 738-751. DOI: 10.6023/cjoc201709045 Published: 05 December 2017 Abstract (1081) PDF (846KB)(2186) Knowledge map Aromatic boronic acids and esters are essential intermediates and have been widely used in biology, medicine and material science. In this paper, the resent progress on their synthesis is summarized, especially Pd-catalyzed borylation of aryl chlorides with steric hindrance substrates, other metal (Ni, Cu, Fe, Zn, Rh, Co)-catalyzed borylation, metal-free borylation, and photoinduced borylation. Reference | Related Articles | Metrics Reviews Recent Advances of α-Aryl Vinyl Azides in Nitrogen Heterocycle Synthesis Yan Jun, Ji Xiaoyue, Hua Shugui, Wang Jing Chin. J. Org. Chem. 2018, 38 (4): 791-801. DOI: 10.6023/cjoc201709025 Published: 15 November 2017 Abstract (899) PDF (599KB)(1433) Knowledge map Nitrogen heterocyclic compounds can be found in various natural products, pharmaceutical chemistry and material chemistry. Due to azide group linked to olefins, α-aryl vinyl azide has unique properties, which can act as electrophilic reagents, nucleophilic reagent, or radical acceptor. Diverse reaction pathways of α-aryl vinyl azide provide great opportunities to generate highly reactive intermediates with unusual or unconventional reactivities, making it possible to develop novel reaction. Recently, more and more synthetic chemists used α-aryl vinyl azide as a key three atoms synthon for the construction of diverse structurally complex N-heterocyclic compounds. This review will introduce systematically the reactivities of α-aryl vinyl azide and the developments of the recent application of α-aryl vinyl azide in nitrogen heterocycle synthesis, including mechanism, reaction characteristics and application study, thus it may be helpful for the research on nitrogen heterocycle synthesis. Reference | Related Articles | Metrics Reviews Recent Advance of Palladium-Catalyzed Cross-Coupling Reactions of Organoalanes with Electrophiles Reagents Li Qinghan, Shao Xuebei, Zhang Gang, Ding Yong, Yang Xuejun, Chen Feng Chin. J. Org. Chem. 2018, 38 (4): 802-811. DOI: 10.6023/cjoc201709041 Published: 15 November 2017 Abstract (451) PDF (662KB)(1073) Knowledge map Organoaluminum compounds are excellent nucleophiles for organic reactions because of their high reactivities, the high Lewis acidity of the aluminum center, and their low toxicities. Therefore, organoalanes are widely applied in cross-coupling reactions. In this paper, recent research results about the organoaluminum reagents applied in cross-coupling reactions catalyzed by palladium are reviewed, involving various reaction systems. Reference | Related Articles | Metrics Cited: CSCD(1) Articles Copper(I)-Catalyzed Non-terminal Enamides Trifluoromethylation: Flexible Synthesis of N-(3,3,3-Trifluoro-2-arylprop-1-en-1-yl) Substituted Benzamide Wang Qing, Gao Kecheng, Zou Jianping, Zeng Runsheng Chin. J. Org. Chem. 2018, 38 (4): 863-870. DOI: 10.6023/cjoc201710025 Published: 08 December 2017 Abstract (565) PDF (490KB)(926) Knowledge map A novel CuI-catalyzed trifluoromethylation of non-terminal enamides was investigated. N-Arylvinyl-substituted benzamide reacted with Togni reagent in dichloroethylane to afford N-(3,3,3-trifluoro-2-arylprop-1-en-1-yl) substituted benzamide. The reaction proceeded at 90℃ in air atmosphere in the presence of base and ligands. Control experiment shows that the Togni reagent firstly released CF3 radical in the presence of copper(I) salts and CF3 radical selectively added to the carbon-carbon double bond of β-position of enamides. Reference | Supporting Info. | Related Articles | Metrics Reviews Advances Research in Synthesis of Aza-heterocyclic Compounds Involving Vinyl Azides Wang Yuying, Liu Li, Wang Yeming Chin. J. Org. Chem. 2018, 38 (5): 1009-1028. DOI: 10.6023/cjoc201711043 Published: 10 January 2018 Abstract (922) PDF (1134KB)(1427) Knowledge map Vinyl azides have been extensively studied in organic synthesis since 1910. As a series of important intermediates, vinyl azides have a wide range of applications in recent years, especially in the synthesis of heterocyclic compounds catalyzed by transition-metals. The progress of the construction of aza-heterocyclic compounds in the field of organic synthesis is reviewed. Reference | Related Articles | Metrics Cited: CSCD(1) Reviews Research Progress of Boronic Acid in Chemsensors Wang Hao, Wang Kai, Sun Jie, Fang Guiqian, Yao Qingqiang, Wu Zhongyu Chin. J. Org. Chem. 2018, 38 (5): 1035-1051. DOI: 10.6023/cjoc201709037 Published: 03 January 2018 Abstract (627) PDF (1738KB)(1664) Knowledge map The detection and fluorescent identification of some substances such as sLea/x in vivo can provide important reference for the diagnosis, treatment and prognosis of disease, molecular tracing and further research on the mechanism of related diseases. Therefore, the development and discovery of high selectivity and high sensitivity chemsensors is of great value. Due to the special structure, phenyl boronic acid compounds could interact and bind with sugar, catecholamine containing catechol structure, fluoride or alkali cyanide. So boronic acids could be develeped as fluorescence sensors selectively for related substances, while have the advantages of high selectivity, high efficiency, rapid analysis and so on. In recent years, boronic acid has been functioned with new materials such as nanoparticles and quantum dots to design novel sensors for better performance. In this paper, the recent progress in the study of boronic acid compounds in sensors is reviewed. Reference | Related Articles | Metrics Articles Switchable Synthesis of Iodoalkynes and Diiodoalkenes from Terminal Alkynes Chen Suo, Zhang Xiaowei, Zhao Hui, Guo Xiaohong, Hu Xiangguo Chin. J. Org. Chem. 2018, 38 (5): 1172-1176. DOI: 10.6023/cjoc201711050 Published: 26 January 2018 Abstract (665) PDF (444KB)(674) Knowledge map Iodoalkynes and diiodoalkenes are valuable intermediates used extensively for C—C, C—O and C—N bonds formation. Therefore, the development of new method for the synthesis of these compunds is desirable. In this work, a novel and switchable protocol for the synthesis of iodoalkynes and diiodoalkenes has been developed, which were formed from terminal alkynes using the same reagent system of ZnI2 and tert-butyl nitrite in the presence or absence of triethylamine, respectively. The iodoalkyne formation is operationally simple, mild (weak base and room temperature), and tolerant of a large range of functional groups. In contrast, the diiodoalkene transformation shows interesting dependence on the electron property, and only electron-rich and neutral compounds are viable substrates. The control experiments performed suggest that iodoalkynes and diiodoalkenes are not interchangeable under a series of reaction conditions, including the optimized conditions, which can be explained by the mechanism in which both of the reactions involve a iodonium intermediate formed directly from a terminal alkyne. Reference | Supporting Info. | Related Articles | Metrics Reviews Progress in Activation of Small Molecules Promoted by Frustrated Lewis Pairs Zhang Zhenbei, Sun Wei, Cao Zhishan Chin. J. Org. Chem. 2018, 38 (6): 1292-1318. DOI: 10.6023/cjoc201801003 Published: 08 March 2018 Abstract (1271) PDF (1322KB)(2385) Knowledge map Frustrated Lewis pairs (FLPs) chemistry has grown rapidly during the last decade and provided a new strategy for the activation of a variety of small molecules, such as hydrogen, olefins, alkynes, carbon dioxide, tetrahydrofuran and hydrosilane etc. The activations of these molecules have probided a new method in the utility of main group element. The structure and reactivity of FLPs are reviewed and the recent progress in activation of small molecules promoted by frustrated Lewis pairs is introduced. Reference | Related Articles | Metrics Reviews Experimental and Computational Research Progress on Cycloadditions of o-Carborane with Unsaturated Compounds Mu Weihua, Cheng Ruijiao, Shang Yingwei, He Renze, Li Dongli, Fu Mian Chin. J. Org. Chem. 2018, 38 (6): 1327-1340. DOI: 10.6023/cjoc201712044 Published: 28 February 2018 Abstract (728) PDF (733KB)(978) Knowledge map o-Carboranes, as well as its derivative o-carborynes, can react with a variety of unsaturated compounds through cycloadditions and transform into various functionalized carboranes which have potential applications in many an area such as boron neutron capture therapy, catalytic systhesis and drug design. Recently, people have made remarkable achievements in the functionalization of o-carboranes and o-carborynes, especially in aspects of reaction condition optimization, selectivity controlling and reaction mechanism exploration. The most recent experimental achievements in the area of cycloaddition between o-carboranes and unsaturated compounds, alkenes, polycyclic or heterocyclic aromatics, in the past ten years are summarized. The reaction mechanisms and corresponding computational findings of o-carboryne-involved [2+2+2],[2+2+1],[2+2],[3+2],[4+2] and[5+2] cycloadditions are summarized and emphasized. Moreover, the prospects of future development in this area are discussed in the end. Reference | Related Articles | Metrics Reviews Recent Progress on Difluoromethylation Methods Wang Weiqiang, Yu Qinwei, Zhang Qian, Li Jiangwei, Hui Feng, Yang Jianming, Lü Jian Chin. J. Org. Chem. 2018, 38 (7): 1569-1585. DOI: 10.6023/cjoc201801041 Published: 27 April 2018 Abstract (1665) PDF (879KB)(2780) Knowledge map The difluoromethyl functional group (CF2H) which has strong lipophilic and electron-withdrawing properties can significantly enhance the physiological activity of organic molecules. The applications of CF2H-containing compounds in the fields of drugs, agrochemicals and so on have attracted great attention of many research groups. Therefore, the development of effective and general methodologies for the selective incorporation of difluoromethyl groups has become one of the hotspots in the field of organic chemistry. Recently, new difluoromethylation reagents and methods that were able to efficiently incorporate the difluoromethyl group under mild conditions have been developed rapidly, that pave the way for the facile introduction of difluoromethyl group into site-specific positions of the target molecules. In this paper, we will first briefly introduce some organic molecules with different functional groups which can be difluoromethylated, and then focus on the development of the recent high-performance difluoromethylation reagents, new reactions and catalysts. Finally, we will discuss the remaining problems and challenges in this particular field. Reference | Related Articles | Metrics Cited: CSCD(2) Reviews Recent Advance of Acyclic Diaryliodonium Salts in Arylation of Heteroatom Ma Jiaoli, Chen Licheng, Yuan Zhongwen, Cheng Huicheng Chin. J. Org. Chem. 2018, 38 (7): 1586-1595. DOI: 10.6023/cjoc201802021 Published: 13 April 2018 Abstract (647) PDF (623KB)(1124) Knowledge map As a kind of low toxicity, environmentally friendly, high reaction activity reagent, hypervalent iodine compounds have received the widespread attention. Acyclic diaryl iodonium salt as aryl cationic reagent, has an important application in organic synthesis. Under mild conditions, diaryl iodonium salt can react with nucleophilic reagent, which has been one of the effective means of the arylation of heteroatom. According to the classification of chemical bond formation, the application of the acyclic diaryl iodonium salt in the arylation of heteroatom (including oxygen, nitrogen, sulfur, phosphorus, etc.) is discussed and the development direction in the field is prospected. Reference | Related Articles | Metrics Cited: CSCD(2) Reviews Recent Advances in Alkaline-Earth-Metal-Catalyzed Hydrofunctionalization Reactions Li Yuanyuan, Cheng Yuhua, Shan Chunhui, Zhang Jing, Xu Dongdong, Bai Ruopeng, Qu Lingbo, Lan Yu Chin. J. Org. Chem. 2018, 38 (8): 1885-1896. DOI: 10.6023/cjoc201804031 Published: 17 May 2018 Abstract (937) PDF (780KB)(1394) Knowledge map Alkaline-earth-metal compounds have been widely concerned due to its abundant reserve and the low-cost. In recent years, alkaline-earth-metal catalysis has achieved great progress in dehydrocoupling, hydroboration, hydrophosphination, hydroamination, hydrosilylation reactions experimentally and therotically. These types of reaction and catalytic mechanism, leading to indentify the role of alkaline-earth-metal in hydrogenation and dehydrogenation reaction are summarized. These reactions, in which the metal-hydride act as active species, generally undergo the reaction pathway involving the cleavage and formation of the metal-hydride covalent bond. The reaction features and mechanisms are generally recognized accrossing to the classification and discussion of these reactions, which would provide guidance for further development of alkaline-earth-metal catalysis. Reference | Related Articles | Metrics Cited: CSCD(2) Articles Insertion Reaction of Benzynes and Stable Sulfur Ylide Li Zhijuan, Jian Hui, Wang Weihua, Wang Qiang, He Lin Chin. J. Org. Chem. 2018, 38 (8): 2045-2053. DOI: 10.6023/cjoc201802003 Published: 03 May 2018 Abstract (682) PDF (539KB)(766) Knowledge map Benzynes undergo insertion reaction with C=S bond of the stable sulfur ylide through a cascade[2+2] cycloaddition and ring-opening reaction to construct a new C-S bond, producing ortho-substituted aryl-alkyl thioether derivatives in moderate to good yields. Reference | Supporting Info. | Related Articles | Metrics Cited: CSCD(1) Notes Synthesis of Titanium Heteroarylphosphinimine Complexes and Application for Ethylene Polymerization Wang Tieshi, Chen Jianjun, Ye Lin, Zhang Aiying, Feng Zengguo Chin. J. Org. Chem. 2018, 38 (8): 2151-2160. DOI: 10.6023/cjoc201803035 Published: 03 May 2018 Abstract (748) PDF (1372KB)(723) Knowledge map Mono-and bisdiphenyl substituted heteroarylphosphines R-PPh2[R=2-pyridyl (3a), 2-thienyl (3b) and 2-furyl (3c)] and Ph2P-R'-PPh2[R'=2,6-pyridyl (6a), 2,5-thienyl (6b) and 2,5-furyl (6c)] were synthesized. After Staudinger reaction with Me3SiN3, those heteroarylphosphines were converted into the heteroarylphosphinimine ligands, R-PPh2(NSiMe3) and (Me3SiN)Ph2P-R"-PPh2(NSiMe3). The subsequently dehalosilylation reaction with CpTiCl3 afforded the corresponding Ti heteroarylphosphinimine halfmetallocenes as olefin polymerization catalysts. The structures of all the complexes were determined by means of 1H NMR, 13C NMR and 31P NMR spectroscopic methods and further confirmed by single-crystal X-ray diffraction analysis. When activated with methylaluminoxane (MAO) at a ratio of Al/Ti=600 and under 0.5 MPa of ethylene, these bimetallic Ti phosphinimine complexes displayed a higher catalytic activity compared to the monometallic analogues, but resulted in polymers with bimodal molecular weight distributions. Unexpectedly, 6b produced ultrahigh Mw polyethylene at lower polymerization temperature. Reference | Supporting Info. | Related Articles | Metrics Reviews Recent Advances in Oxidative Coupling Reaction Catalyzed by Low-Valence Iodine Yan Yizhe, Cui Chang, Li Zheng Chin. J. Org. Chem. 2018, 38 (10): 2501-2518. DOI: 10.6023/cjoc201805016 Published: 15 June 2018 Abstract (835) PDF (1059KB)(1378) Knowledge map In recent years, low-valence iodine-catalyzed oxidative coupling reaction has made rapid progress, providing an effective method for the construction of C—C, C—O, C—N, C—S, C—P and other chemical bonds. Compared with the transition metal-catalyzed oxidation coupling reaction, this protocol is metal-free under mild conditions. It avoids the high cost and toxicity of transition metal catalyst, which meets the requirements of green chemistry. Therefore, iodine catalysis has attracted much attention of the synthetic chemists. The research progress on low-valence iodine-catalyzed oxidative coupling from 2010 to now is summarized, and outlook of this field is also prospected. Reference | Related Articles | Metrics Cited: CSCD(2) Reviews Recent Advances in Transition Metal-Promoted Trifluoromethylation Reactions Chen Donghan, Yang Wen, Yao Yongqi, Yang Xin, Deng Yingying, Yang Dingqiao Chin. J. Org. Chem. 2018, 38 (10): 2571-2589. DOI: 10.6023/cjoc201803045 Published: 06 June 2018 Abstract (1016) PDF (956KB)(2744) Knowledge map Recently, transition metal-promoted trifluoromethylation has been developed rapidly. Starting with the types of transition metal that promote the trifluoromethylation reactions, the research progress of trifluoromethylation promoted by silver, iron, palladium, nickel, rhodium and cobalt in recent years is reviewed. Moreover, the possible mechanisms of some parts of reactions are also discussed. Reference | Related Articles | Metrics Reviews State of the Art in Germanium-Containing Aromatic Systems Cui Jingjing Chin. J. Org. Chem. 2018, 38 (11): 2888-2895. DOI: 10.6023/cjoc201805049 Published: 05 July 2018 Abstract (484) PDF (616KB)(733) Knowledge map Germanium-containing conjugated compounds are regarded as powerful candidates for the development of optoelectronic material. As a subclass of germanium-containing conjugated compounds and a crucial type of the heavy analogues of aromatic compounds, germanium-containing aromatic hydrocarbons (Ge-AHs) have attracted much attention and developed rapidly in recent days. According to the charge of the Ge-AHs, these species were categorized into three subclasses:neutral, anionic and cationic species. Herein, the synthetic methodology together with the reactivity of these reported Ge-AHs is summarized and the parameters used for the evaluation of the aromaticity of these compounds is highlighted. Ge-AHs and aromatic hydrocarbons share similar structural and magnetic properties. However, their major reactivity is quite different. This review will not only inspire the discovery of new structures and reactivities of Ge-Ahs, but also help to form a deeper understanding of the concept of aromaticy. Reference | Related Articles | Metrics Cited: CSCD(1) Reviews Application of Mesitylboronic Acid and Its Esters in Coupling Reactions Wu Yao, Dou Zhengjie, Wu Caimei, Chen Huabao, Zhang Zumin, Wang Xianxiang, Yin Zhongqiong, Song Xu, He Changliang, Yue Guizhou Chin. J. Org. Chem. 2018, 38 (11): 2896-2926. DOI: 10.6023/cjoc201804027 Published: 05 July 2018 Abstract (653) PDF (1378KB)(1141) Knowledge map Organic boronic reagents have played a critical role in the field of organic synthesis, especially Suzuki coupling, since they were founded. In return, all kinds of transition metal (Pd, Ni, Rh, Au etc.)-catalyzed coupling reactions have given a big push for the development and application of organic boronic reagents. 2,4,6-Mesitylboronic acid was used widely in various coupling reactions, including Suzuiki reaction, aromatic C-H activation, oxidative Heck reaction, carbonlation, decarboxylation, photoredox reaction and other C-X (C-N, C-S, C-Se) bonding reaction, which was used to synthesize functional materials, ligands and drug molecules. This paper includes two aspects:(1) reviewing the application of mesityl boronic acid and its ester in coupling reaction, and (2) making our points and respecting for this field. Reference | Related Articles | Metrics Articles Palladium/Copper(I) Acetate-Promoted Desulfurative Coupling of Pyrimidine Thioether with Alkynes or Arylboronic Acids Liu Boqu, Yan Zhongfei, Quan Zhengjun Chin. J. Org. Chem. 2018, 38 (11): 3032-3038. DOI: 10.6023/cjoc201803025 Published: 16 July 2018 Abstract (536) PDF (466KB)(629) Knowledge map An efficient method for carbon-carbon bond formation via desulfurative coupling of pyrimidine thioethers/4-phenylquinoline thioethers with alkynes or arylboronic acids is described. The reaction was promoted by a cheap and stable copper salt[copper(I) acetate] and catalyzed by palladium with good yields and wild substrate scope. Reference | Supporting Info. | Related Articles | Metrics Articles Phosphoryl Protecting Group Enabled Facile Synthesis of Unsymmetrical 1,3-Diynes by Selective Hay Coupling Peng Lifen, Peng Chao, Wang Ming, Tang Zilong, Jiao Yinchun, Xu Xinhua Chin. J. Org. Chem. 2018, 38 (11): 3048-3055. DOI: 10.6023/cjoc201805009 Published: 05 July 2018 Abstract (556) PDF (511KB)(603) Knowledge map A selective Hay coupling reaction of aromatic terminal acetylenes and monophosphoryl-protected diynes was developed. The polarity of Ph2P(O) realized facile isolation of the desired unsymmetrical 1,3-diynes from by-products. The low reactivity of monophosphoryl-protected diynes reduced the oxidative homocoupling of itself and enhanced the yields of desired products. A number of aromatic terminal acetylenes and monophosphoryl-protected diynes were tolerated in this reaction, and all the corresponding unsymmetrical 1,3-diynes could be obtained in moderate to good yields. The unsymmetrical 1,3-diynes could be applied to synthesize unsymmetrical yne-diynes and cyclic polyynes. Reference | Supporting Info. | Related Articles | Metrics Articles Copper-Catalyzed Hydroxytrifluoromethylthiolation of Arylpropynones Hu Juanjuan, Huang Yangen, Xu Xiuhua, Qing Fengling Chin. J. Org. Chem. 2019, 39 (1): 177-182. DOI: 10.6023/cjoc201808041 Published: 12 November 2018 Abstract (705) PDF (452KB)(844) Knowledge map Recently, the preparation of fluorinated compounds through difunctionalization strategies has become a hot research area in fluorine chemistry. In this work, a copper-catalyzed hydroxytrifluoromethylthiolation of arylpropynones for the synthesis of the corresponding trifluoromethylthiolated enols was developed. The copper salt and solvent are crucial to the yields of this reaction. Under optimized reaction conditions, a series of trifluoromethylthiolated enols were obtained in moderate to good yields. Reference | Supporting Info. | Related Articles | Metrics Articles Addition of Perfluoroalkanesulfenic Acids to Alkynes and Allenes Li Xiaobo, Zhao Juan, Liu Qian, Jiang Min, Liu Jintao Chin. J. Org. Chem. 2019, 39 (1): 183-191. DOI: 10.6023/cjoc201808036 Published: 26 October 2018 Abstract (518) PDF (497KB)(726) Knowledge map The addition reaction of perfluoroalkanesulfenic acids, in-situ formed from imines, to alkynes and allenes were investigated. A series of perfluoroalkyl alkenyl sulfoxides were synthesized. Markovnikov adducts were obtained in good to excellent yields from the reactions of aryl or alkyl-substituted alkynes with perfluoroalkanesulfenic acids under mild conditions. However, the reaction of terminal alkynes containing an electron-withdrawing group afforded Michael-type adducts in good yields. The addition reaction of electron-rich allenes took place at the double bond with less steric hindrance, while the double bond connecting an electron-withdrawing group was the prior reaction site in the case of electron-deficient allenes. Reference | Supporting Info. | Related Articles | Metrics Articles Synthesis of Perfluoroalkylated Fluorenes with Phosphonate Group via One-Pot Synthesis Process Sun Xiaoli, Sun Zhenhua, Han Minmin, Han Jing, He Weimin, Chen Jie, Deng Hongmei, Shao Min, Zhang Hui, Cao Weiguo Chin. J. Org. Chem. 2019, 39 (1): 192-199. DOI: 10.6023/cjoc201808028 Published: 20 October 2018 Abstract (640) PDF (724KB)(572) Knowledge map A simple and versatile metal-free protocol for the synthesis of perfluoroalkyated fluorene derivatives bearing phosphonate group is achieved. The reactions proceeded via one-pot three-component condensation of indenones, fluorinated alkynylphosphonates and malononitrile under mild conditions. This protocol is highly regioselective, operationally facile and applicable to a variety of indenones in good to excellent yields. Reference | Supporting Info. | Related Articles | Metrics Articles Nickel-Catalyzed Difluoromethylation of (Hetero)aryl Bromides with BrCF2H Gao Xing, He Xu, Zhang Xingang Chin. J. Org. Chem. 2019, 39 (1): 215-222. DOI: 10.6023/cjoc201808014 Published: 12 October 2018 Abstract (1148) PDF (490KB)(1491) Knowledge map A nickel-catalyzed direct difluoromethylation of (hetero)aryl bromides with bromodifluoromethane (BrCF2H) is described. This reaction features high efficiency, broad substrate scope and high functional group tolerance, providing a cost-efficient and straightforward route for applications in medicinal chemistry. Preliminary mechanistic studies reveal that a nickel-based, reductive cross-coupling catalytic cycle is involved in the reaction. Reference | Supporting Info. | Related Articles | Metrics Articles Trifluoromethylthiolation/Oxidation of Styrenes for Facile Synthesis of α-Trifluoromethylthio Acetophenons Wang Jian-Yong, Ma Lan, Li Yan, Wang Xi-Sheng Chin. J. Org. Chem. 2019, 39 (1): 232-237. DOI: 10.6023/cjoc201807052 Published: 12 November 2018 Abstract (711) PDF (513KB)(899) Knowledge map Trifluoromethylthiolation/oxidation of styrenes with easiy-handling AgSCF3 used as the trifluoromethylthiolating reagent has been described, which furnished a series of α-trifluoromethylthio acetophenons. A variety of substituted styrene could be bifunctionalized via radical process in a mixed solvent of dimethyl sulfoxide (DMSO) and CHCl3, with potassium persulfate used as the oxidant under mild conditions. A simple and efficent method for the facile construction of various α-trifluoromethylthio acetophenons is thus demonstrated. Reference | Supporting Info. | Related Articles | Metrics Articles Pentafluoroethyl-Substituted Sulfonium Ylides: New Electrophilic Pentafluoroethylating Reagents Liu Yafei, Ge Hangming, Lu Long, Shen Qilong Chin. J. Org. Chem. 2019, 39 (1): 257-264. DOI: 10.6023/cjoc201807018 Published: 10 September 2018 Abstract (835) PDF (461KB)(720) Knowledge map Two electrophilic pentafluoroethylating reagents of pentafluoroethyl(p-methylphenyl)sulfonium bis(carbometh- oxy)methylide (4a) and pentafluoroethyl(4-nitrophenyl)sulfonium bis(carbomethoxy)methylide (4b), and their reactions under mild conditions with β-ketoesters, aryl iodides and heteroaromatics are described. Reference | Supporting Info. | Related Articles | Metrics Notes Synthesis of Vicinal Trifluoromethanesulfonate Substituted Diaryliodonium Salts and Their Anti-bacterial Properties Cui Liyuan, Chen Huangguan, Ma Jingyi, Han Jianwei, Wang Limin Chin. J. Org. Chem. 2019, 39 (1): 270-276. DOI: 10.6023/cjoc201808043 Published: 17 December 2018 Abstract (714) PDF (1796KB)(1094) Knowledge map Diaryliodonium salts with fluorines have potential bioactivity. Vicinal trifluoromethanesulfonate substituted diaryliodonium salts were synthesized for the purpose of studying their anti-bacterial properties aganist Escherichia coli (E. coli), Staphylococcus aureus (S. aureus) and Bacillus subtilis (B. subtilis). Firstly, their chemical structures were characterized by 1H NMR, 13C NMR, 19F NMR and mass spectra. The minimum inhibitory concentration (MIC) of these compounds was tested by the micro-broth dilution method. The most active 2-((3-fluorophenyl)(((trifluoromethyl)sulfonyl)oxy)-l3-iodanyl)- phenyl trifluoromethanesulfonate (1) containing fluorine group gave the promising results for Escherichia coli (E. coli), Staphylococcus aureus (S. aureus) and Bacillus subtilis (B. subtilis) (MIC values of 16, 4 and 4 μg·mL-1), which is significantly lower than the commercial antibacterial agent of isothiazolinones. Scanning electron microscope (SEM) analysis sugggested that the compound led to the death of bacteria. Cytotoxicity tests showed that the compound 1 as well as isothiazolinones had a slight effect on the growth of Hela cells in vitro conditions. Reference | Related Articles | Metrics Notes Palladium-Catalyzed Dehydrative Cross Couplings of Stabilized Phosphorus Ylides with Allylic Alcohols Ma Xiantao, Yu Jing, Ma Ruitian, Yan Ran, Zhang Zhenlei Chin. J. Org. Chem. 2019, 39 (3): 830-835. DOI: 10.6023/cjoc201812051 Published: 22 February 2019 Abstract (697) PDF (503KB)(862) Knowledge map A dehydrative cross coupling of ketone-stabilized phosphorus ylides with the readily available allylic alcohols followed by an one-pot Wittig reaction is developed. A range of functional 1,4-dienes could be obtained in 52%~95% isolated yields in the presence of 5 mol% Pd(PPh3) 4 and 20 mol% B(OH) 3. The same method can be extended to ester or nitrile-stabi-lized phosphorus ylides, affording the corresponding 1,4-dienes in moderate yields. Reference | Supporting Info. | Related Articles | Metrics Reviews Progress of Trifluoromethylation Using Trifluoroacetic Acid and Its Derivatives as CF3-Sources Ji Xiaoming, Shi Guangfa, Zhang Yanghui Chin. J. Org. Chem. 2019, 39 (4): 929-939. DOI: 10.6023/cjoc201810033 Published: 21 December 2018 Abstract (1365) PDF (752KB)(2265) Knowledge map Organic molecules containing trifluoromethyl groups often exhibit unique physical and chemical properties, and have found extensive applications. Trifluoroacetic acid and its derivatives have advantages including low cost, ready availability and high stability. Furthermore, CO2 is the byproduct. Therefore, trifluoroacetic acid and its derivatives are ideal trifluoromethylating reagents, and have great application potentials. The progress of trifluoromethylation reactions using trifluoroacetic acid and its derivatives as CF3-sources is reviewed, including the reactions of C-X (X=Br and I), C-H, and C=X (X=C, O). The mechanisms are also introduced. Reference | Related Articles | Metrics Articles Synthesis and Biological Activities of 1,3,4-Thiadiazole Triazene Compound Zhang Mingqian, Liu Binkai, Lei Qiang, Yan Jingdong, Zhao Zhongyu, Long Yue Chin. J. Org. Chem. 2019, 39 (4): 1064-1069. DOI: 10.6023/cjoc201809003 Published: 21 December 2018 Abstract (677) PDF (514KB)(730) Knowledge map Using the splicing principle of combining the pharmacological group triazene with 1,3,4-thiadiazole, 15 unreported 1,3,4-thiadiazole triazene derivatives were synthesized. The structures of the compounds were determined by nucleated magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). By using the typical triazene drug dacarbazine (DTIC) and drug 5-fluorouracil (5-FU) as a reference, the activity detections of human esop-hageal cancer cells (EC109), human gastric cancer cells (MGC803), and human prostate cancer cells (PC-3) were carried out. The results showed that some compounds inhibited human gastric cancer cells (MGC803) more strongly than dacarbazine (DTIC), and the IC50 values of compounds 2-(3-methyanilino)-5-[4-(3,3-dimethyltriazol-1-yl) phenyl]-1,3,4-thiadiazole (8c), 2-(2-methoxyanilino)-5-[4-(3,3-dimethyltriazol-1-yl) phenyl]-1,3,4-thiadiazole (8f), and 2-(3,4-dichloroanilino)-5-[4-(3,3-di-methyltriazol-1-yl) phenyl]-1,3,4-thiadiazole (8l) were lower than those of 5-fluorouracil with 5.3, 6.5 and 6.3 μmol/L, respec-tively. Some compounds inhibited human prostate cancer cells (PC-3) more strongly than dacarbazine (DTIC), and the IC50 value of 8l is lower than that of 5-fluorouracil with 13.5 μmol/L. Reference | Supporting Info. | Related Articles | Metrics Articles I2O5 Promoted Iodosulfonylation of Alkynes with Sulfonylhydrazides to Synthesis (E)-β-Iodovinyl Sulfones under Peroxide-Free Conditions Tang Yucai, Ran Shutong, Wang Ping, Chen Piao Chin. J. Org. Chem. 2019, 39 (4): 1116-1121. DOI: 10.6023/cjoc201810002 Published: 07 December 2018 Abstract (614) PDF (866KB)(647) Knowledge map A facile and efficient I2O5 promoted iodosulfonylation of alkynes for direct synthesis of (E)-β-iodovinyl sulfones is described. This procedure affords various synthetically useful β-iodosulfonyl alkenes in moderate to good yields under peroxide free conditions. Reference | Supporting Info. | Related Articles | Metrics Notes Tetrabutylammonium Iodide Promoted Thioetherification of Arylsulfonylhydrazides with 4-Hydroxycoumarins Zhu Fuyuan, Wang Yanmei, He Mingchuang, Yan Zhaohua, Lin Sen Chin. J. Org. Chem. 2019, 39 (4): 1175-1180. DOI: 10.6023/cjoc201810005 Published: 30 November 2018 Abstract (706) PDF (844KB)(1037) Knowledge map A facile approach for thioetherification of 4-hydroxycoumarins with arylsulfonyl hydrazides promoted by tetrabutylammonium iodide in the presence of hydrochloric acid was developed generating a series of 3-arylthio-4-hydroxycoumarins in 65%~94% yields. Broad scope and easy availability of substrates, simple operation and high yields of products are the advantages of this method. Reference | Supporting Info. | Related Articles | Metrics Reviews Progress in the Synthesis and Applications of Phosphaalkenes Huang Haiyang, Ding Haixin, Xu Shuangshuang, Bai Jiang, Xiao Qiang Chin. J. Org. Chem. 2019, 39 (5): 1263-1276. DOI: 10.6023/cjoc201811038 Published: 31 January 2019 Abstract (704) PDF (810KB)(983) Knowledge map The phosphaalkenes, as an important part of organophosphorus chemistry, play a very important role in the field of homogeneous catalysis and functional materials due to special properties of P=C unit. However, the difficult access to phosphaalkene compounds and their less stability have severely retarded the progress of the phosphaalkene chemistry. In this paper, the recent advances in phosphaalkenes, introducing the properties, synthetic methods, and applications of phosphaalkenes to provide some reference for related researcher are reviewed. Reference | Related Articles | Metrics Cited: CSCD(1) page Page 1 of 2 Total 66 records First page Prev page Next page Last page