有机氟化学合辑 Default Latest Most Read Please wait a minute... ARTICLES Electrochemical Trifluoromethylation/Spirocyclization of N-Benzylacrylamides to Construct Trifluoromethylated 2-Azaspiro[4.5]decanes Lan Zhou, Hong He, De-Qiao Yang, Zhong-Wei Hou, Lei Wang Chinese Journal of Organic Chemistry 2024, 44 (3): 981-988. DOI: 10.6023/cjoc202310032 Published: 29 December 2023 Abstract (235) HTML (29) PDF (476KB)(233) Knowledge map An electrochemical trifluoromethylation/spirocyclization of N-benzylacrylamides with CF3SO2Na as the source of trifluoromethyl group has been developed. This approach is carried out in a simple undivided cell at room temperature without relying on metal-reagents and oxidants, which provides a green and efficient route to construct a series of CF3-containing 2-azaspiro[4.5]decanes. Furthermore, the gram-scale synthesis and transformation can be easily performed. Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Dual Photoredox/Copper Catalysis Enabled Three-Component Defluorinative Alkylboration of Alkenes Tian Ye, Yifeng Wang Chinese Journal of Organic Chemistry 2024, 44 (2): 663-664. DOI: 10.6023/cjoc202400008 Abstract (117) HTML (7) PDF (422KB)(170) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES [3+2] Cyclization of Difluoroacetohydrazonoyl Bromides with β-(N,N-Dimethylamino)enones/Enoates/Enamides Xiaoyong Li, Danfeng Huang, Yuxiu Zhou, Xiaokang Liu, Kehu Wang, Junjiao Wang, Yulai Hu Chinese Journal of Organic Chemistry 2024, 44 (4): 1226-1239. DOI: 10.6023/cjoc202311001 Published: 29 December 2023 Abstract (374) HTML (11) PDF (757KB)(288) Knowledge map A [3+2] cyclization of difluoromethyl nitrile imines generated in situ from difluoroacetohydrazonoyl bromides with β-(N,N-dimethylamino)enones/enoates/enamides in the presence of base is described. The cycloaddition reaction pro- duced the pyrazoline intermediates, from which 3,4-disubstituted-3-difluoromethylpyrazoles were obtained in moderate to good yields via spontaneous elimination of the Me2NH molecule. The reaction is fully regioseclective by the interaction of lowest unoccupied molecular orbital (LUMO) of the 1,3-dipoles and highest occupied molecular orbital (HOMO) of electron-rich alkenes (inverse-electron-demand). This approach expands the types of [3+2] cyclization involved difluoro- methyl nitrile imines, which provides a simple, efficient and novel method for the synthesis of 3-difluoromethylpyrazoles. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Three-Component Reaction Involving Alkenes, AgSCF3 and Quinoxalinones Initiated by Trifluoromethylthio Radical Shenyuan Gao, Haoqiong Zhu, Qiaoling Jin, Lu'er Jin, Xiaozhong Wang, Liyan Dai Chinese Journal of Organic Chemistry 2024, 44 (4): 1264-1275. DOI: 10.6023/cjoc202310002 Published: 08 December 2023 Abstract (173) HTML (4) PDF (525KB)(224) Knowledge map A novel three-component cascade radical reaction involving non-activated olefins, quinoxalin-2(1H)-ones, and AgSCF3 was proposed. Under the action of the oxidizing agent K2S2O8, 40 quinoxaline derivatives containing SCF3 were obtained with the highest yield of 78%. This method provides a mild and environmentally friendly approach to prepare trifluoromethylthio-substituted quinoxalines, offering advantages such as high yield, broad substrate scope, atom economy, and environmental efficiency. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Piezoelectric Material-Mediated Mechanosynthesis of Aryl Fluorides Hong Pan, Guanwu Wang Chinese Journal of Organic Chemistry 2023, 43 (11): 4010-4011. DOI: 10.6023/cjoc202300062 Abstract (165) HTML (11) PDF (434KB)(199) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Pd/IPrBIDEA-Catalyzed Hydrodefluorination of gem-Difluorocyclopropanes: Regioselective Synthesis of Terminal Fluoroalkenes Jie Jia, Ying Xia Chinese Journal of Organic Chemistry 2023, 43 (11): 4017-4018. DOI: 10.6023/cjoc202300065 Abstract (221) HTML (15) PDF (437KB)(304) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Palladium-Catalyzed C(sp3)—Si Bonds Transformation for Construct-ing Trifluoropropyl (Hetero)arenes through C(sp3)—C(sp2) Cross-Coupling Reactions Junjun Liu, Taotao Lu, Ping Ma, Qingyang Zhao, Fuk Yee Kwong Chinese Journal of Organic Chemistry 2024, 44 (4): 1319-1326. DOI: 10.6023/cjoc202310013 Published: 23 November 2023 Abstract (182) HTML (4) PDF (575KB)(219) Knowledge map Palladium-catalyzed C(sp3)—Si bonds transformation of commercially available polyalkoxy trifluorosilane reagents has been developed through C(sp3)—C(sp2) cross-coupling reactions. This Hiyama cross-coupling reaction shows good functional group tolerance and provides a series of trifluoropropyl (hetero)arenes. The fluoride source and alkyl tether of bisphosphine ligand play important roles in improving yields. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS Progress in the Application of Fluorine-Substituted Organic Hole Transport Materials for Perovskite Solar Cells Dong Liu, Xiaoye Zhang, Zhanfeng Li Chinese Journal of Organic Chemistry 2024, 44 (4): 1197-1209. DOI: 10.6023/cjoc202307008 Published: 15 November 2023 Abstract (260) HTML (5) PDF (953KB)(383) Knowledge map Perovskite solar cells (PSCs) are of significant importance in the fields of environment, ecology, and energy structure adjustment due to their exceptional performance, cost-effectiveness, and straightforward preparation process. Among them, hole transport materials (HTMs) play a crucial role in PSCs by effectively regulating the battery interface barrier, facilitating hole transport and collection, reducing charge recombination, optimizing the perovskite layer-electrode interface, and enhancing the properties of perovskite light absorption layer. Fluorine-substituted materials possess unique charge transport and photoelectric properties. The introduction of fluorine atoms into organic molecules through induction and conjugation effects can lower molecular energy levels, improve HTM hole mobility thereby enhancing PSCs performance. This paper provides a comprehensive review and summary on the impact of fluorine-substituted organic hole transport materials on the photoelectric properties of PSCs as well as their underlying mechanisms. Fig. & Tab. | Reference | Related Articles | Metrics Visible-Light-Mediated Trifluoromethylalkynylation of Unactivated 1,6-Dialkenes Yinxia Cai, Chao Liu Chinese Journal of Organic Chemistry 2023, 43 (10): 3669-3671. DOI: 10.6023/cjoc202300058 Abstract (162) HTML (10) PDF (375KB)(234) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Photocatalytic Synthesis of Alkyl Trifluoromethyl Ketones Mengjie Cen, Tieqiao Chen Chinese Journal of Organic Chemistry 2023, 43 (10): 3675-3677. DOI: 10.6023/cjoc202300060 Abstract (222) HTML (19) PDF (446KB)(288) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES N-Heterocyclic Carbene-Catalyzed Synthesis of Pentafluorophenyl Sulfides Dengpeng Xia, Jinyun Luo, Lin He, Zhihua Cai, Guangfen Du Chinese Journal of Organic Chemistry 2024, 44 (2): 622-630. DOI: 10.6023/cjoc202306014 Published: 26 October 2023 Abstract (180) HTML (4) PDF (564KB)(202) Knowledge map An efficient method for the construction of C(sp2)—S bond has been developed. The stable N-heterocyclic carbene 1,3-bis(2,6-dissopropylphenyl)-imidazole-2-ylidene can activate the C—Si bond of pentafluorophenyl trimethylsilicon effectively to initiate the nucleophilic substitution reaction with thiosulfonic ester, producing pentafluorophenyl sulfide products in 34%~98% yields. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Visible-Light Induced Organophotocatalysis for the Synthesis of Difluoroethylated Benzoxazines Xiang Chen, Wen-Tao Ouyang, Xiao Li, Wei-Min He Chinese Journal of Organic Chemistry 2023, 43 (12): 4213-4219. DOI: 10.6023/cjoc202307026 Published: 15 September 2023 Abstract (318) HTML (24) PDF (808KB)(453) Knowledge map Benzoxazines are important motif in pharmaceuticals and functional molecules. A visible-light induced photocatalytic strategy for the synthesis of difluoroethyl benzoxazines with organo-photocatalyst was developed. In the present protocol, a series of olefinic amides can be transferred to difluoroethylated benzoxazines via oxydifluoromethylation with CF2HSO2Na as difluoromethylating reagent, which is easily operated and good functional group tolerant. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds Yukun Jin, Baoyi Ren, Fushun Liang Chinese Journal of Organic Chemistry 2024, 44 (1): 85-110. DOI: 10.6023/cjoc202307004 Published: 08 September 2023 Abstract (451) HTML (16) PDF (3203KB)(508) Knowledge map The unique properties of difluorinated compounds have attracted widespread attention in the fields of medicine and material sciences. The conversion of inexpensive and easily available trifluoromethyl groups into difluoro groups is of great importance in organic synthesis. However, there still exist great challenges in the selective cleavage of C—F bonds, because the dissociation energy of single C—F bond in trifluoromethyl group is much higher than that of the C—F bond in the difluoro unit of the generated product. Thus, the selective cleavage of C—F bond is difficult to control, which can easily lead to excessive defluorination. Compared with the traditional thermal reaction, the visible-light irradiated reaction provides an alternative pathway to achieve C—F cleavage more efficiently and selectively. The research progress on the selective cleavage of C—F bonds mediated by visible light in the past three years is summarized and its future perspective is prospected. Fig. & Tab. | Reference | Related Articles | Metrics Palladium-Catalyzed Fluorinative Bifunctionalization of Aziridines and Azetidines with gem-Difluorocyclopropanes Yaxin Zeng, Ying Xia Chinese Journal of Organic Chemistry 2023, 43 (9): 3331-3333. DOI: 10.6023/cjoc202300052 Abstract (294) HTML (22) PDF (405KB)(335) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Synthesis of (Bromodifluoromethyl)trimethylsilane and Its Applications in Organic Synthesis Zhi Tu, Jinsheng Yu, Jian Zhou Chinese Journal of Organic Chemistry 2023, 43 (10): 3491-3507. DOI: 10.6023/cjoc202306024 Published: 30 August 2023 Abstract (414) HTML (19) PDF (1049KB)(550) Knowledge map Bromodifluoromethyl trimethylsilane (TMSCF2Br) has proved to be an important difluoromethyl(alkyl)ation reagent that is widely applied in organic synthesis over the past decade, since it was used as a difluorocarbene precursor in 2011. This review aims to provide a briefly summary for the synthesis of TMSCF2Br, and to introduce the recent advances in the applications of TMSCF2Br as a difluorocarbene or trimethylsilyldifluoromethyl radical precursor for developing various difluoromethyl(alkyl)ations of different kinds of substrates. Meanwhile, the activation ways of TMSCF2Br and the possible mechanism, as well as its advantages and disadvantages in each kind of reactions are detailedly disccussed, which might provide some references and inspiration for researchers engaged in organic synthesis and organic fluorine chemistry. Fig. & Tab. | Reference | Related Articles | Metrics Research of Visible Light/Lewis Base Dual Catalytic Defluorinative Silylation of Trifluoromethyl-Substituted Alkenes Jiajie Zhu, Yi Wan, Qiyang Yuan, Jinlian Wei, Yongqiang Zhang Chinese Journal of Organic Chemistry 2023, 43 (10): 3623-3634. DOI: 10.6023/cjoc202304034 Published: 20 July 2023 Abstract (332) HTML (15) PDF (831KB)(714) Knowledge map A novel photoredox/Lewis base dual-catalytic defluorinative silylation reaction of trifluoromethylsubstituted alkenes for the synthesis of gem-difluoroallylsilanes is reported, where silylboranes are employed as the silyl donor reagents. The protocol proceeds via the catalytic activation of Si—B bond by a Lewis base quinuclidine and the formation of silyl radical, making it easy to scale up. It features mild and green reaction conditions, simple reaction system, broad substrate scope and good functional group compatibility. Furthermore, the potential of this class of building blocks in the construction of various gem-difluoromethyl-containing structures has been also demostrated. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Recent Development of SuFEx Reaction between Silyl Ethers and Sulfur(VI) Fluoride Compounds Hao Zhang, Qingbin Zhao, Zhongrui Ruan, Zhenxing Liu Chinese Journal of Organic Chemistry 2023, 43 (10): 3569-3579. DOI: 10.6023/cjoc202304026 Published: 26 June 2023 Abstract (308) HTML (8) PDF (765KB)(404) Knowledge map The last decade has witnessed the great development of SuFEx reactions. The synthetic value of SuFEx reactions in the preparation of small molecules and polymers is reviewed. The paper is arranged based on the types of substrates and the possible direction of the reaction is discussed. Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Enantioselective Nucleophilic Trifluoromethoxylation of Racemic Propargyl Sulfonates Chuanfa Ni, Jinbo Hu Chinese Journal of Organic Chemistry 2023, 43 (7): 2582-2583. DOI: 10.6023/cjoc202300039 Abstract (216) HTML (12) PDF (352KB)(318) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen Chinese Journal of Organic Chemistry 2023, 43 (9): 3239-3245. DOI: 10.6023/cjoc202301023 Published: 25 May 2023 Abstract (287) HTML (15) PDF (532KB)(365) Knowledge map A supporting electrolyte-free method for the electrochemical synthesis of trifluoromethylated oxindoles in conti- nuous flow was developed. Various N-arylacrylamides reacted with CF3SO2NHNHBoc smoothly to provide the corresponding products in moderate yields. The reaction scale-up was easily realized without changing the reaction conditions, which showed the application potential of continuous flow electrochemical synthesis. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Synthesis of 3-Trifluoromethylpyrazole Derivatives Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu Chinese Journal of Organic Chemistry 2023, 43 (9): 3257-3267. DOI: 10.6023/cjoc202302026 Published: 25 May 2023 Abstract (352) HTML (15) PDF (636KB)(314) Knowledge map The [3+2] cycloaddition reactions of trifluoroacetohydrazonoyl bromides with ynones, alkynoates and aynamides have been developed, and a series of 3-trifluoromethylpyrazole derivatives were obtained in medium to excellent yields. The noble features of this protocol include excellent regioselectivity, good functional group tolerance, mild reaction conditions and simple operation. It provides an efficient and practical method for the synthesis of 3-trifluoromethylpyrazoles. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li Chinese Journal of Organic Chemistry 2023, 43 (8): 2913-2925. DOI: 10.6023/cjoc202303004 Published: 10 April 2023 Abstract (361) HTML (8) PDF (757KB)(493) Knowledge map In this study, a visible-light photoredox-catalyzed difluoroalkylation of newly designed functionalized aromatic isocyanides with commercially available CF2 precursors was reported. A series of CF2-containing indole-1,2-fused diazepanones were constructed in cascade reaction through a sequence of radical addition/cyclization processes under mild conditions. This reaction not only generated a class of polycyclic indole fused seven-membered nitrogen heterocycles but also expanded the reactions of functionalized isocyanides. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Near-Infrared Visualization Fluoroboron Dipyrrole (BODIPY) Fluore-scent Probe with Large Stokes Shift for Detecting Na2S2O4 in vivo Xiaolong Zhao, Liangwu Guo, Yuqing Li, Qiyuan Ran, Huihui Wu, Zhen Zhang, Yingpeng Su, Pengxin Zhou, Na Yan Chinese Journal of Organic Chemistry 2023, 43 (7): 2484-2491. DOI: 10.6023/cjoc202210011 Published: 24 March 2023 Abstract (314) HTML (18) PDF (2758KB)(423) Knowledge map Based on the main skeleton of fluoroboron dipyrrole (BODIPY), two near-infrared fluorescent probes Azo-BDP1 and Azo-BDP2 were rationally designed and synthesized with large Stokes shift of 217 and 224 nm, respectively. As two visualized probes for Na2S2O4, Azo-BDP1 and Azo-BDP2 exhibited high sensitivity and selectivity. The reaction-based recognition mechanism was confirmed by mass spectral analysis, in addition, fluorescence imaging studies in zebrafish embryos and zebrafish proved that the probe Azo-BDP1 is suitable for the detection of Na2S2O4 in vivo. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Reversible Mechanofluorochromic and Data Security Protection of a Triphenylamine-Based Difluoroboron Luminescent Compound Maocai Xu, Jiazhuang Tian, Yanhua Yang, Gaozhang Gou, Fumin Li, Lin Shao, Kexin Chi Chinese Journal of Organic Chemistry 2023, 43 (5): 1824-1831. DOI: 10.6023/cjoc202211030 Published: 17 March 2023 Online available: 17 March 2023 Abstract (360) HTML (11) PDF (3105KB)(468) Knowledge map In order to meet the demand of data storage security in the rapid development of information, a π-conjugated triphenylamine-based difluororboron compound (PyTPABF2) was designed and successfully synthesized. PyTPABF2 held positive solvatochromism behavior, intramolecular charge transfer property, aggregation-induced emission behavior and high contrast mechanofluorochromic performance. The as-prepared powders PyTPABF2 exhibited bright green fluorescence (533 nm), which luminescent color switching to khaki (556 nm) under external mechanical stimulation, meanwhile, the color could recover to original state after fuming. The X-ray diffraction (XRD) measurement demonstrated that this phenomenon originated from the process of phase transformation between crystalline and amorphous. More importantly, PyTPABF2-based data secu-rity paper could be achieved rewritable storage of information. It was of assistance in the rational design of smart luminescent materials. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Selective Mono- and Di-deuterodefluorination of Trifluoroacetamides Promoted by Boryl Radicals Qiuyu Gu, Tianyu Peng, Mingcheng Bo, Yifeng Wang Chinese Journal of Organic Chemistry 2023, 43 (5): 1832-1842. DOI: 10.6023/cjoc202212030 Published: 07 March 2023 Online available: 07 March 2023 Abstract (409) HTML (18) PDF (557KB)(560) Knowledge map Deuterated mono- and difluoroalkyl groups have attracted increasing attention in medicinal and biological studies. Controllable snipping one or two fluorine atoms from widely accessible trifluoromethyl groups followed by deuteration is an attractive method to access these molecules, whereas this has been hindered by the challenges associated with the chemoselectivity control during the defluoriantion process. Herein, a strategy for chemoselective deuterodefluorination reaction of trifluoro- and difluoroalkylacetamides via spin-center shifts is reported. The reaction starts with the attack of a deuterated 4-dimethylaminopyridine-boryl radical (DMAP-BD2) to the amide oxygen atom, followed by a spin-center shift process to trigger the C—F bond scission. The resulting α,α-difluorocarbonyl radicals undergo deuterium atom transfer to afford the CF2D-products in high yields and high levels of D-incorporation. Notably, increasing the amount of DMAP-BD3 enables the selective cleavage of the two C—F bonds, leading to CFD2-products in good yields meanwhile maintaining good levels of D-incorporation. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS Progresses on Fluorocarbon-Containing Substrates Involved Carbonylation Reactions Da-Lie An, Zhi-Peng Bao, Xiao-Feng Wu Chinese Journal of Organic Chemistry 2023, 43 (7): 2304-2312. DOI: 10.6023/cjoc202301010 Published: 07 March 2023 Online available: 07 March 2023 Abstract (430) HTML (17) PDF (662KB)(622) Knowledge map The synthesis and transformation of fluorine-containing organic molecules has experienced vigorously development and has become one of the most important frontier topics of fluorine chemistry, which profoundly affects life science and material science. Among them, carbonylative transformation of fluorocarbon-containing substrates is a carbonylation reaction developed in recent years which still has many challenges. This review summarized the progresses on fluorocarbon-containing substrates carbonylation reactions based on transition metal palladium, nickel and copper catalysis. In order to understand the mechanism of these reactions, representative reactions were selected for detailed discussion. Fig. & Tab. | Reference | Related Articles | Metrics REVIEWS Research Progress of Reaction-Based Probes for Detecting Fluoride Ion Yanjie Qu, Yajun Li, Hongli Bao Chinese Journal of Organic Chemistry 2023, 43 (3): 809-825. DOI: 10.6023/cjoc202302015 Published: 01 March 2023 Abstract (574) HTML (40) PDF (1644KB)(1114) Knowledge map Fluoride ion is closely related to human life activities. Excessive or too little fluoride ions in human body will cause pathological changes. Therefore, it is necessary to develop appropriate measures to detect the fluoride ion content in human body and environment. Colorimetry and fluorescence detection have attracted much attention due to their high selectivity, high sensitivity and fast response. Herein, reaction-based fluoride ion probes are introduced. According to the reaction mechanisms, these probes can be divided into five types: interactions between fluoride ion and boronic acid derivatives, fluoride ion-promoted cleavage of Si—C bond, fluoride ion-promoted cleavage of Si—O bond, fluoride ion-induced dehydrogenation, fluoride ion-promoted cleavage of P—O bond. Not only the detection method of the probe is introduced, but also the action mechanism of some examples is described. Fig. & Tab. | Reference | Related Articles | Metrics Triflylpyridinium Promoted Controllable Reduction of Carboxylic Acids to Aldehydes Shencheng Qian, Mingqiang Xue Chinese Journal of Organic Chemistry 2023, 43 (2): 783-785. DOI: 10.6023/cjoc202300008 Abstract (369) HTML (20) PDF (367KB)(786) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Electrochemical Cobalt-Catalyzed C-H Hydroxyalkylation of N-Heteroarenes with Trifluoromethyl Ketones Huiqiao Wang, Kun Xu Chinese Journal of Organic Chemistry 2023, 43 (2): 789-790. DOI: 10.6023/cjoc202300010 Abstract (255) HTML (18) PDF (441KB)(422) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles Jinxiao Zhao, Tonghui Wei, Sen Ke, Yi Li Chinese Journal of Organic Chemistry 2023, 43 (3): 1102-1114. DOI: 10.6023/cjoc202212032 Published: 23 February 2023 Abstract (430) HTML (30) PDF (845KB)(644) Knowledge map Polycyclic indoles are widely found in natural products and pharmaceutical molecules, and have a wide range of applications in the pharmaceutical, pesticide and dye industries. Although considerable development has been made in the synthesis of indole polycycles, it is still of great scientific interest and value to explore more efficient and milder experimental strategies for the synthesis of highly-functionalized polycyclic indoles. Herein, a one-step radical tandem cyclization reaction to synthesize difluoroalkylindoles with quaternary carbon centers by using difluorobromoesters as the fluorine source and 3-alkenyl indoles as the substrates under visible light-catalyzed conditions was developed. The method is easy-to-operate and mild in conditions, with a wide range of substrate adaptability and good yields, providing a green and efficient synthetic route for fluorine-containing polycyclic indoles. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds Chengfu Zeng, Yuan He, Qing Li, Lin Dong Chinese Journal of Organic Chemistry 2023, 43 (3): 1115-1123. DOI: 10.6023/cjoc202210033 Published: 07 February 2023 Online available: 08 February 2023 Abstract (346) HTML (11) PDF (473KB)(348) Knowledge map Ir(III)-catalyzed three-component cascade reaction to construct unique trifluoroethoxylation amide compounds has been developed, meanwhile the fluorinated compounds could continue to react with alcohols to prepare complex spiro isoindolinone derivatives in one-pot. The highly efficient approaches produce various amide compounds by condition- controlled. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers Rui Wang, Lang Gao, Cen Zhou, Xiao Zhang Chinese Journal of Organic Chemistry 2023, 43 (3): 1136-1145. DOI: 10.6023/cjoc202211013 Published: 18 January 2023 Abstract (850) HTML (45) PDF (1624KB)(752) Knowledge map Photocatalytic heterogeneous chlorotrifluoromethylation and iodoperfluoroalkylation of unactivated terminal alkenes have been achieved under the catalysis of phenylphenothiazine-based porous organic polymer (PTH-POP). This method offers a transition-metal-free and recyclable platform to access valuable perfluoroalkylated compounds in a highly efficient fashion. Fig. & Tab. | Reference | Related Articles | Metrics Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines Xiaoyu Lu, Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao Chinese Journal of Organic Chemistry 2023, 43 (6): 2110-2119. DOI: 10.6023/cjoc202208010 Published: 12 January 2023 Abstract (309) HTML (9) PDF (695KB)(433) Knowledge map A protocol for the copper-catalyzed decarboxylative cross-coupling of α‑fluoroacrylic acids with N-tosyl oxaziridines was reported. A series of substituted α-fluoroacrylic acids, and primary, secondary and tertiary substituted oxaziridines were suitable reaction substrates. The decarboxylation reaction exhibited good functional group compatibility and excellent Z-stereoselectivity. This method provides a novel and practical strategy for the construction of monofluoroalkenes, which are key functional groups in the pharmaceutical and material sciences. In addition to α-fluoroacrylic acids, β- fluoroacrylic acid could also participate in the reaction smoothly, which provides a protocol to access various substituted monofluoroalkenes. This methodology also provides a platform for the modification of complex biologically active molecules. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Difluorocarbene-Enabled Synthesis of 3-Substituted-2-oxoindoles from o-Vinylanilines Hua Huang, Xin Li, Jianke Su, Qiuling Song Chinese Journal of Organic Chemistry 2023, 43 (3): 1146-1156. DOI: 10.6023/cjoc202210031 Published: 21 December 2022 Abstract (424) HTML (8) PDF (587KB)(537) Knowledge map A novel transition-metal-free protocol for the synthesis of 1-alkyl-3-(2-oxo-2-aryl/alkyl-ethyl)indolin-2-ones is developed. This work reveals that oxoindole skeletons can be directly constructed from ortho-vinylanilines and commercially available halogenated difluoroalkyl reagents via a C—N cleavage/new C—N bonds and C—C bond formation cascade. This reaction portrays high efficiency and excellent functional group compatibility, and has great potential in the late-stage modifications of pharmaceutical molecules and natural products. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Photocatalyzed 2∶2 Coupling of Styrene and BrCF2CO2Me: A Facile Synthesis of Bis-difluoroacetylated Hexestrol Derivatives Shenhao Chen, Song Zou, Chanjuan Xi Chinese Journal of Organic Chemistry 2023, 43 (3): 1157-1167. DOI: 10.6023/cjoc202210009 Published: 14 December 2022 Abstract (539) HTML (15) PDF (875KB)(454) Knowledge map Photoredox-catalyzed 2∶2 coupling of styrene and BrCF2CO2Me is reported, which undergoes a homo-coupling of in situ generated β-CF2CO2Me substituted benzyl radical. The reaction features a wide substrate scope and functional group tolerance to afford bis-difluoroacetylated hexestrol derivatives with high yields. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics HIGHLIGHTS Nickel-Catalyzed Defluorinative Asymmetric Cyclization of Fluoroalkyl-Substituted 1,6-Enynes for the Synthesis of Seletracetam Quan Lin, Hegui Gong Chinese Journal of Organic Chemistry 2022, 42 (12): 4356-4357. DOI: 10.6023/cjoc202200073 Abstract (271) HTML (9) PDF (483KB)(323) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Facile Synthesis of Allylic gem-Difluorides Enabled by Novel 3,3-Difluoroallyl Sulfonium Salts Zhi-Qiang Li, Cheng-Qiang Wang, Chao Feng Chinese Journal of Organic Chemistry 2022, 42 (11): 3906-3908. DOI: 10.6023/cjoc202200065 Abstract (272) HTML (6) PDF (497KB)(308) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Ring Opening Amination of gem-Difluorocyclopropanes with Cyclobutanone Hydrazones Zhipeng Liang, Hao Ye, Haibin Zhang, Guomin Jiang, Xinxing Wu Chinese Journal of Organic Chemistry 2023, 43 (4): 1483-1491. DOI: 10.6023/cjoc202208031 Published: 12 December 2022 Abstract (435) HTML (24) PDF (539KB)(652) Knowledge map N-Fluoroallyl hydrazones with four-ring structure were effectively synthesized using cyclobutanone hydrazones and gem-difluorocyclopropanes as raw materials through palladium catalyzed ring opening of difluorocyclopropanes and nucleophilic capture process of nitrogen nucleophile. This protocol shows broad substrate scope and good functional group tolerance, which can be applied for gram-scale preparation. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Visible-Light-Promoted Direct Trifluoromethylation of Tryptophan-Containing Oligapeptides with YlideFluor Jing Liu, Jian Hao, Qilong Shen Chinese Journal of Organic Chemistry 2023, 43 (4): 1517-1524. DOI: 10.6023/cjoc202209018 Published: 22 November 2022 Online available: 22 November 2022 Abstract (506) HTML (17) PDF (805KB)(545) Knowledge map A photosensitizer-free visible-light-promoted method for site-selective trifluoromethylation of tryptophan- containing oligopeptides using YlideFluor as the trifluoromethyl radical source under mild conditions was developed. Mechanistic studies showed that a donor-acceptor between 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and YlideFluor is generated. Upon irradiation with blue LEDs, the S—CF3 bond in the adduct undergoes homolytic cleavage to give trifluoromethyl radical, which attacks the electron-rich C-2 position of the indole moiety in the tryptophan-containing oligopeptide. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Recent Progress in Selective C-F Bond Activation of Trifluoromethyl Alkenes Shuyong Song, Senmiao Xu Chinese Journal of Organic Chemistry 2023, 43 (2): 411-425. DOI: 10.6023/cjoc202210016 Abstract (642) HTML (53) PDF (790KB)(964) Knowledge map Selective C-F bond activation of the trifluoromethyl group is an important approach for the synthesis of gem-difluoro compounds. Given the importance of trifluoromethyl alkenes in synthetic chemistry as well as their diversity in selectivity, the research on selective C-F bond activation of these compounds has received considerable interest. To this end, The research progress is summarized, including nucleophilic addition/defluorination (SN2' type), acid-promoted defluorinative Friedel-Crafts arylation, (formal) ipso-defluorinative functionalization, and transition-metal-catalyzed migratory insertion/ defluorination. Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Selective Trifluoromethiolation and Difluoromethiolation of Pyridines at C(3) Position Feng Chen, Fengling Qing Chinese Journal of Organic Chemistry 2022, 42 (10): 3423-3424. DOI: 10.6023/cjoc202200055 Abstract (313) HTML (15) PDF (443KB)(321) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics page Page 1 of 2 Total 76 records First page Prev page Next page Last page