Default Latest Most Read Please wait a minute... Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis Yingjie Liu, Gangqing Shi, Ge Chou, Xin Zhang, Dongxue Song, Ning Chen, Miao Yu, Ying Xu Chinese Journal of Organic Chemistry 2023, 43 (8): 2664-2681. DOI: 10.6023/cjoc202305011 Published: 27 July 2023 Abstract (497) HTML (28) PDF (1012KB)(756) Knowledge map Ethers are widely used in organic chemistry, materials science, biomedicine and other fields due to their excellent physicochemical properties. Among them, tetrahydrofuran/tetrahydrothiophene and their derivatives are the core backbones for building biologically active molecules and complex natural products. In recent years, photo/electrocatalysis has gradually become an important tool for chemists to synthesize novel compounds due to its compliance with the requirements of green chemistry and the unique pathway that mostly involves radical intermediates. The functionalization of α-positions of ethers using photo/electrocatalysis is a green and efficient synthetic strategy. Therefore, the research progress of photo/electro- catalytic functionalization of ether compounds at the α-position is reviewed with ether/sulfide as examples, and a detailed description of some of the mechanisms is provided. Fig. & Tab. | Reference | Related Articles | Metrics REVIEWS Research Progress in Synthesis of Spirocyclic Compounds Driven by Photo/Electrochemistry Ning Chen, Chengdong Zhang, Peng Li, Ge Qiu, Yinjie Liu, Tianlei Zhang Chinese Journal of Organic Chemistry 2023, 43 (7): 2293-2303. DOI: 10.6023/cjoc202304014 Published: 26 June 2023 Abstract (509) HTML (30) PDF (706KB)(768) Knowledge map As important organic molecular frameworks, spirocycles exist widely in organic chemistry, medicinal chemistry, material science and other fields. Since the spirocyclic skeleton has a large three-dimensional space structure, which meets the demand for conformational rigidity in drug design, it is particularly important to develop efficient synthetic methods for spirocyclic compounds. In recent years, photocatalysis and electrocatalysis have injected new potential into the synthesis of spirocyclic compounds as green and efficient synthetic methods. This article is mainly classified by the construction of snail [4.5] skeleton, snail [5.5] skeleton, snail [2.3] skeleton, and spiro-indoles skeleton. Moreover, the construction of spirocyclic compounds is reviewed from two aspects: photocatalysis and electrocatalytic synthesis. Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Electroreductive Dicarboxylation of Unactivated Skipped Dienes with CO2 to Synthesize Cyclic Dicarboxylic Acid Jian Huang, Wenzhen Zhang Chinese Journal of Organic Chemistry 2023, 43 (7): 2580-2581. DOI: 10.6023/cjoc202300038 Abstract (291) HTML (19) PDF (343KB)(336) 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 (313) HTML (16) PDF (532KB)(430) 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 Electrochemical Mediated Esterification Reaction of Carboxylic Acids and Alcohols Yunzhe Zhong, Ying hen, Lei Yu, Hongwei Zhou Chinese Journal of Organic Chemistry 2023, 43 (8): 2855-2863. DOI: 10.6023/cjoc202302004 Published: 23 April 2023 Abstract (593) HTML (27) PDF (581KB)(769) Knowledge map A series of esters were prepared by electrochemical synthesis of carboxylic acids with alcohols. This protocol can be carried out at room temperature without inert atmosphere, strong acids or metal catalysts, etc. The esterification reaction processes in an undivided electrolytic cell with constant current mode and the esterification products are generated in good yields. Compared with esterification promoted by organic reagents, this protocol avoids the byproducts which have to be separated by column chromatography and successful for tertiary alcohol which is generally difficult to undergo esterification directly, providing a new access to the esterification of carboxylic acids and alcohols. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics HIGHLIGHTS Electrooxidative Cobalt-Catalyzed Regio- and Enantioselective Annulation of Benzamides with Alkenes Dandan Yang, Junlong Niu Chinese Journal of Organic Chemistry 2023, 43 (5): 1887-1889. DOI: 10.6023/cjoc202300027 Abstract (305) HTML (10) PDF (447KB)(389) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Electrochemical Synthesis of Masked Organoboronic Acids RB(dan) at Room Temperature Junying Zhang, Xiaojing Zhao, Ganpeng Li, Yonghui He Chinese Journal of Organic Chemistry 2023, 43 (5): 1815-1823. DOI: 10.6023/cjoc202211033 Published: 17 March 2023 Online available: 17 March 2023 Abstract (378) HTML (19) PDF (533KB)(527) Knowledge map An electrochemical room-temperature synthesis of masked organoboronic acids RB(dan) (R=alkyl or aryl) has been developed. At room temperature, 1,8-diaminonaphthalene and boronic acids can smoothly participate in this reaction to provide a wide variety of RB(dan) (R=alkyl or aryl) in an undivided cell. The transformation has broad substrate scope and avoids using high-temperature or transition-metal catalysts, making it more sustainable and renewable. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS Photochemical and Electrochemical Borylation Involving Aryl and Alkyl Compounds Linlin Du, Hua Zhang Chinese Journal of Organic Chemistry 2023, 43 (5): 1726-1741. DOI: 10.6023/cjoc202212041 Published: 17 March 2023 Online available: 17 March 2023 Abstract (901) HTML (72) PDF (977KB)(1231) Knowledge map Organoboron compounds are important building blocks in organic synthesis and have been widely applied in materials and pharmaceutical science. The development of practical and concise borylation reactions to synthesize organoboron compounds has always been one of the core topics of organoboron chemistry. Recently, photochemical and electrochemical borylation reactions have gained rapid development and emerged as important methods towards the synthesis of organoboron compounds. The recent research progress concerning photochemical, electrochemical and photoelectrochemical borylation involving aryl and alkyl compounds from the view of energy resources and substrates is reviewed. Additionally, research trends of this area are also discussed. 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 (278) HTML (19) PDF (441KB)(531) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Alternating Current Promoted Silver Catalysis for C—H Phosphorylation Na Chen, Haichao Xu Chinese Journal of Organic Chemistry 2023, 43 (3): 1199-1200. DOI: 10.6023/cjoc202300012 Abstract (277) HTML (19) PDF (348KB)(570) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics REVIEWS Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process Zhongrong Xu, Jieping Wan, Yunyun Liu Chinese Journal of Organic Chemistry 2023, 43 (7): 2425-2446. DOI: 10.6023/cjoc202212035 Published: 07 February 2023 Online available: 08 February 2023 Abstract (775) HTML (26) PDF (947KB)(923) Knowledge map Thiocyano and selenocyano are both important functional groups with broad application in organic synthesis. Such functional structures also occur frequently in molecules possessing valuable biological and pharmaceutical activities, optical functions, and catalytic profiles. Therefore, developing synthetic methods toward diverse organo thio-/selenocyanates as well as the tandem annulation for the construction of diverse heterocyclic scaffolds keep receiving high interests. The advances on the synthesis of organo thio-/selenocyanates via transition metal-free C—H thiocyanation or selenocyanation as well as the tandem annulation reactions based on such C—H functionalization are reviewed. Fig. & Tab. | Reference | Related Articles | Metrics Electrochemically Promoted Halogenation of Imidazoland-[1,2-a]pyridine with Dichloro(bromo)ethylene and Iodoform Zhou Zhang, Yu Guo, Jing Yang, Dan Wu, Jiaxin Wang, Xinyue Hong, Peijun Cai, Liangce Rong Chinese Journal of Organic Chemistry 2023, 43 (6): 2104-2109. DOI: 10.6023/cjoc202212014 Published: 18 January 2023 Abstract (349) HTML (15) PDF (496KB)(736) Knowledge map An electrochemical halogenation of 2-arylimidazoland[1,2-a]pyridine with dichloro(bromo)ethylene and iodoform is reported. Studies show that dichloroethane, dibromoethane and iodoform are excellent halogen source reagents in this synthesis. The present protocol provides alternative route to obtain 3-halogenatedimidazo[1,2-a]pyridines derivatives. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS Recent Progress in Electrochemical Fixation of CO2 to Construct Carboxylic Acid Derivatives Yongzhou Pan, Xiujin Meng, Yingchun Wang, Muxue He Chinese Journal of Organic Chemistry 2023, 43 (4): 1416-1434. DOI: 10.6023/cjoc202208004 Published: 15 November 2022 Abstract (640) HTML (37) PDF (786KB)(1053) Knowledge map CO2 is an important C1 source in organic synthesis due to its abundant, non-toxic and low-cost properties. There- fore, it is of great significance to use CO2 as a C1 source to synthesize compounds with high added value. This review focuses on the recent progress in the carboxylation of organic compounds using CO2 as an electrophile under electrochemical conditions. The electrochemical carboxylation of non-activated organic halides, unsaturated alkene compounds and some special compounds are mainly introduced. And the use of sacrificial anodes and non-sacrificial anodes is classified in detail. The reaction mechanisms of these reactions are also discussed. This review provides a reference for the application of such reactions in organic synthesis in the future. Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Electrochemical Allylic Alkylation of Morita-Baylis-Hillman Adducts and N-Hydroxyphthalimide Esters towards C(sp3)—C(sp3) Bond Formation Li Sun, Guoxin Song, Jiale Han, Jiyu Li, Yue Zhao, Luhua Yang, Feng Zhang, Kun Zhao, Biming Mao Chinese Journal of Organic Chemistry 2023, 43 (4): 1574-1583. DOI: 10.6023/cjoc202209024 Published: 15 November 2022 Abstract (483) HTML (23) PDF (515KB)(484) Knowledge map A redox-free, electroreductive approach to achieve allylic alkylation by employing Morita-Baylis-Hillman (MBH) adducts is reported. A critical feature of this transformation is that neither external chemical oxidants nor metal catalysts are required. Alkyl radical produced by electron reduction with N-hydroxyphthalimide (NHP) esters, displaying broad tolerance of functional groups and alkene substitution patterns in high stereoselectivity and regioselectivity. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Cobalt-Catalyzed Electrochemical Reductive Coupling of Alkynes and Alkenes Shiquan Gao, Chuangjun Liu, Junfeng Yang, Junliang Zhang Chinese Journal of Organic Chemistry 2023, 43 (4): 1559-1565. DOI: 10.6023/cjoc202209036 Published: 15 November 2022 Abstract (697) HTML (29) PDF (581KB)(869) Knowledge map Transition-metal-catalyzed coupling reactions have now been extensively studied. However, the traditional reaction generally requires the addition of excessive amount of oxidant or reductive reagent. The new reaction mode of electro-organic synthesis avoids the usage of stoichiometric amount of redox reagent, which is more in line with the concept of green chemistry and atom economy. Recently cobalt catalysis has been discovered to be a cheap and low toxic alternative to noble transition-metal catalysts. In this paper, the reductive coupling reaction between alkynes and alkenes has been developed via electrochemistry by cobalt catalysis. The product could be delivered up to 90% yield with excellent regioselectivity. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei Chinese Journal of Organic Chemistry 2023, 43 (2): 756-762. DOI: 10.6023/cjoc202206023 Published: 01 November 2022 Abstract (558) HTML (11) PDF (546KB)(608) Knowledge map Thioester compounds have been widely applied in the synthesis of bioactive chemicals, natural products and organic materials due to their versatile reactivities. In recent years, the decarboxylation coupling reactions between α-keto acids and thiols/thiophenols have been utilized to access thioesters. Herein, an electrochemical decarboxylation coupling method has been established, which uses α-keto acids and thiophenols as the starting materials and affords thioesters in moderate to good yields. This protocol features simple manipulation and avoids usually needed metal-based catalysts, bases or external oxidants, thus providing a new, mild, and green pathway to synthesize thioester compounds. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Electrochemical Oxidative C(sp3)—H Sulfonylation of Xanthenes with Sodium Sulfinates Bin Wei, Zilong Zhou, Jinghao Qin, Zeyu Yan, Jiacheng Guo, Shu Lei, Yexiang Xie, Xuanhui Ouyang, Renjie Song Chinese Journal of Organic Chemistry 2023, 43 (1): 186-194. DOI: 10.6023/cjoc202207012 Published: 15 September 2022 Online available: 15 September 2022 Abstract (509) HTML (30) PDF (714KB)(799) Knowledge map A direct electrochemical sulfonylation of C(sp3)—H bonds of xanthenes with sodium sulfinates was studied. A wide variety of 9-(arylsulfonyl)-9H-xanthenes and 9-(alkylsulfonyl)-9H-xanthenes were constructed in a single step at room temperature. This reaction proceeded through a radical pathway and a new C—S bond was formed under this electrochemical sulfonylation transformation. The significant advantages of this strategy include transition metal- and additional oxidant-free, mild reaction conditions, operational simplicity, broad substrate scope and excellent functional group tolerance. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS Research Progress of Electrochemical Synthesis of C-Sulfonyl Compounds Wanjie Wei, Lei Zhan, Lei Gao, Guobao Huang, Xianli Ma Chinese Journal of Organic Chemistry 2023, 43 (1): 17-35. DOI: 10.6023/cjoc202205018 Published: 25 August 2022 Abstract (715) HTML (39) PDF (1094KB)(868) Knowledge map Sulfonyl compounds are important organic sulfur compounds, which are widely used in the fields of medicine, pesticides, functional materials and so on. Therefore, efficient strategies for the synthesis of sulfonyl compounds have become the focus of extensive research. Organic electrochemical synthesis is a green, mild and efficient synthesis strategy, which shows great potential in the synthesis of sulfonyl compounds. The reactions of electrochemical synthesis of C-sulfonyl compounds in recent years are introduced. The reactions of electrochemical synthesis of C(sp)-sulfonyl compounds, C(sp2)-sulfonyl compounds and C(sp3)-sulfonyl compounds are classified, summarized and discussed, and the corresponding reaction mechanism is described, so as to provide reference for the application of such reactions in organic synthesis in the future. Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Photoelectrocatalytic Site- and Enantioselective Cyanation of Benzylic C—H Bonds Shaoyu Li, Jie Wu Chinese Journal of Organic Chemistry 2022, 42 (11): 3903-3905. DOI: 10.6023/cjoc202200064 Abstract (330) HTML (20) PDF (444KB)(503) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Electrochemical Oxidative Thiocyanosulfonylation of Aryl Acetylenes Yu Zheng, Shencheng Qian, Pengcheng Xu, Binnan Zheng, Shenlin Huang Chinese Journal of Organic Chemistry 2022, 42 (12): 4275-4281. DOI: 10.6023/cjoc202209041 Published: 12 December 2022 Abstract (604) HTML (17) PDF (882KB)(602) Knowledge map Thiocyano and sulfonyl groups as important functional groups are widely existing in natural products, agrochemicals and medicines. They are also versatile synthetic intermediates that could be converted into various functionalities. There are limited reports on the synthesis of compounds that contain these two functional groups. A simple three-component thiocyanatosulfonylation of aryl acetylenes with sodium sulfinates and NH4SCN through electrochemical oxidation to construct thiocyanated vinylsulfones has been established. The reaction employs easily accessible starting materials and features the characterization of external oxidant-free, mild reaction conditions, and high stereoselectivity. Moreover, this method enables two C—S bonds to be simultaneously formed in a one-step reaction. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Electrocatalytic Three-Component Synthesis of 4-Bromopyrazoles from Acetylacetone, Hydrazine and Diethyl Bromomalonate Siyu Mu, Hongxia Li, Zhilin Wu, Junmei Peng, Jinyang Chen, Weimin He Chinese Journal of Organic Chemistry 2022, 42 (12): 4292-4299. DOI: 10.6023/cjoc202211002 Published: 28 November 2022 Abstract (518) HTML (17) PDF (916KB)(679) Knowledge map Pyrazoles are the most important five-membered N-heterocycles as they are present in many natural products and synthetic drugs. Among various pyrazole derivatives, 4-bromopyrazoles have attracted great attention because they not only display significant biological activities and physicochemical properties but also serve as valuable synthons in organic chemistry. In this manuscript, an efficient and eco-friendly method for the synthesis of various 4-bromopyrazoles through three- component reaction of hydrazine, acetylacetone and 2-bromomalonate was reported and the proposal reaction mechanism was revealed. According to the mechanism, hydrazine reacts with acetylacetone to afford pyrazole firstly, which then converts to 4-bromopyrazole through bromination. This method could also be well applicable for the bromination of other heterocyclic compounds. Given the high oxidation state of diethyl 2-bromomalonate, the peroxidation can be avoided through the electrolysis process, thus the excess amount of brominating agent was not be required. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS C-3 Functionalization of 2-Aryl-2H-indazoles under Photo/Electrocatalysis Danfeng Wang, Jin Wang, Chunhua Ma, Yuqin Jiang, Bing Yu Chinese Journal of Organic Chemistry 2022, 42 (12): 4024-4036. DOI: 10.6023/cjoc202208039 Published: 08 November 2022 Abstract (741) HTML (30) PDF (684KB)(1009) Knowledge map 2H-Indazole is a privileged scaffold widely existing in drugs and bioactive molecules. The C—H functionalization of 2H-indazole is the cutting edge in medicinal chemistry and organic chemistry. Compared with traditional synthetic methods, the visible light/electrochemical-promoted synthetic method has mild conditions and is an environmentally friendly synthetic strategy. The C—H functionalization of 2-aryl-2H-indazoles at the C-3 position catalyzed by photochemical/electrochemical strategies in recent years is summarized in terms of catalytic systems, with special emphasis on the corresponding reaction mechanism, which might inspire the further development of new catalytic methods. Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Electrocarboxylation of Aryl Epoxides with CO2 to Selectively Synthesize β-Hydroxy Acids Wenjun Xie, Liangnian He Chinese Journal of Organic Chemistry 2022, 42 (10): 3427-3428. DOI: 10.6023/cjoc202200057 Abstract (332) HTML (8) PDF (434KB)(451) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Transition-Metal-Free, Electrophotocatalyzed Selective C—F Arylation of Polyfluoroarenes Kejin Jiao, Tiansheng Mei Chinese Journal of Organic Chemistry 2022, 42 (10): 3421-3422. DOI: 10.6023/cjoc202200054 Published: 12 October 2022 Abstract (563) HTML (25) PDF (434KB)(595) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Electrochemical Oxidative Cross-Dehydrogenative Coupling of Five-Membered Aromatic Heterocycles with NH4SCN Hongxia Li, Peng Chen, Zhilin Wu, Yuhan Lu, Junmei Peng, Jingyang Chen, Weimin He Chinese Journal of Organic Chemistry 2022, 42 (10): 3398-3404. DOI: 10.6023/cjoc202207009 Published: 18 August 2022 Abstract (639) HTML (21) PDF (522KB)(550) Knowledge map A practical method for the synthesis of various thiocyanated 5-membered aromatic heterocycles through electrochemical cross-coupling of heterocycles (pyrazoles, pyrroles, furans and thiophenes) with NH4SCN under chemical oxidant- and exogenous electrolyte-free conditions was developed. NH4SCN played dual roles of a supporting electrolyte and a thiocyanated reagent, and thus simplify the reaction system. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS Recent Progress on the Electrochemical Difunctionalization of Alkenes/Alkynes Xiuying Li, Pingfang Tao, Yongyu Cheng, Qiong Hu, Weijuan Huang, Yun Li, Zhihui Luo, Guobao Huang Chinese Journal of Organic Chemistry 2022, 42 (12): 4169-4201. DOI: 10.6023/cjoc202204066 Published: 09 September 2022 Online available: 09 September 2022 Abstract (1449) HTML (63) PDF (1786KB)(1815) Knowledge map The difunctionalization of unsaturated hydrocarbons (alkenes or alkynes) is an important strategy to introduce functional groups, and is also an important method to synthesize polysubstituted hydrocarbons, which is widely used in the fields of total synthesis of natural products and drug synthesis. The latest research progress on the electrochemically enabled difunctionalization of alkenes or alkynes in recent five years is summarized. According to the classification of difunctionalization of alkenes and cyclization of unsaturated hydrocarbon, the application and the related reaction mechanism are introduced. It is hoped that this review can be referred to the future application in organic synthesis of electrochemic- mediated difunctionalization of alkenes/alkynes. Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Synthesis of Nitrile via Electrochemical Appel Reaction Haiqiong Li, Mengyun Yin, Fenfen Xie, Zhengbing Zhang, Pan Han, Linhai Jing Chinese Journal of Organic Chemistry 2022, 42 (7): 2229-2235. DOI: 10.6023/cjoc202202007 Published: 22 March 2022 Abstract (708) HTML (23) PDF (623KB)(647) Knowledge map An electrochemical Appel reaction was developed for the synthesis of nitriles. This protocol features operationally simplicity, mild reaction conditions and environmental friendliness, enabling synthesis of various aromatic and aliphatic nitriles. Based on the controlled experiments and cyclic voltammetry (CV) experimental results, an electrochemical Appel reaction mechanism was proposed to explain the reaction process. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Electrochemical Synthesis of N-Acyl/Sulfonylsulfenamides Using Potassium Iodide as Mediator Zhaoxin Wei, Renjie Wang, Yonghong Zhang, Bin Wang, Yu Xia, Weiwei Jin, Chenjiang Liu Chinese Journal of Organic Chemistry 2022, 42 (11): 3730-3739. DOI: 10.6023/cjoc202205026 Published: 21 July 2022 Abstract (435) HTML (15) PDF (1508KB)(488) Knowledge map An efficient and environmentally friendly electrocatalytic protocol has been developed for synthesizing N-acyl/ sulfonyl sulfenamides. In an undivided cell, various electron-deficient groups substituted amines and aryl thiols react smoothly to afford the N—S bond formation products in 36%~98% yields. Preliminary mechanistic studies indicate that the reaction may work through a free radical process. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics HIGHLIGHTS Asymmetric Synthesis of Indolyl C—N Atropoisomers through Enantioselective Electrophilic Amination Wei Liu, Xiaoyu Yang Chinese Journal of Organic Chemistry 2022, 42 (8): 2596-2598. DOI: 10.6023/cjoc202200042 Abstract (402) HTML (10) PDF (460KB)(1185) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics NOTE Electrochemical Migratory Cyclization of N-Acylsulfonamides Tao Wang, Weisi Guo Chinese Journal of Organic Chemistry 2022, 42 (7): 2259-2260. DOI: 10.6023/cjoc202200036 Abstract (511) HTML (17) PDF (458KB)(346) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Cobalta-Electrocatalyzed Allylic C—H Alkylation Huiqiao Wang, Kun Xu Chinese Journal of Organic Chemistry 2022, 42 (4): 1260-1261. DOI: 10.6023/cjoc202200021 Abstract (543) HTML (34) PDF (453KB)(624) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHTS Alternating Current Promoted Radical-Radical Cross Coupling Na Chen, Hai-Chao Xu Chinese Journal of Organic Chemistry 2022, 42 (2): 650-651. DOI: 10.6023/cjoc202200007 Abstract (455) HTML (15) PDF (410KB)(553) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Electrochemical Synthesis of Aryl Sulfonates from Sodium Sulfinates and Phenols under Metal-Free Conditions Zhengjiang Fu, Zhenjiang Yang, Li Sun, Jian Yin, Xuezheng Yi, Hu Cai, Aiwen Lei Chinese Journal of Organic Chemistry 2022, 42 (2): 600-606. DOI: 10.6023/cjoc202107060 Abstract (794) HTML (22) PDF (740KB)(821) Knowledge map An electrochemical oxidative sulfonylation of phenols with sodium sulfinates has been established to produce arylsulfonyl esters with good functional group tolerance in moderate to high yields. The synthesis of chlorfenson and a gram-scale reaction have been performed to evaluate the practicality of this green protocol. Cyclic voltammetry experiments indicate that the oxidation of sulfinate occurs prior to that of phenol substrate under standard conditions, and free radical is involved in the process. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Electrochemical Oxidative C—H Trifluoromethylation of Quinoxalin-2(1H)-ones and the Performance Evaluation via Electro-descriptors Xiaolong Guo, Yuxian Wang, Zhiqiang Zhao, Qing Wang, Jian Zuo, Luyao Wang Chinese Journal of Organic Chemistry 2022, 42 (2): 641-649. DOI: 10.6023/cjoc202108023 Abstract (491) HTML (13) PDF (1023KB)(460) Knowledge map An operationally simple electrochemical oxidative C—H trifluoromethylation of quinoxalin-2(1H)-ones was achieved by employing the inexpensive, readily available and easy processing CF3SO2Na as CF3 source. In the absence of any catalysts or oxidant reagents, this method is more in line with the requirements of green and sustainable development. Most importantly, “electric-descriptor-diagram” was used to evaluate the reaction substrates. The reactive/non-reactive boundary and the trend of yield change can been clearly seen. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Electrochemical Oxidative Trifluoromethylation of α-Oxoketene Ketene Dithioacetals with CF3SO2Na Qingyun Gu, Zhenfeng Cheng, Xiaobao Zeng Chinese Journal of Organic Chemistry 2022, 42 (5): 1537-1544. DOI: 10.6023/cjoc202112024 Published: 21 January 2022 Abstract (734) HTML (20) PDF (663KB)(626) Knowledge map An efficient electrochemical oxidative trifluoromethylation of α-oxoketene dithioacetals with CF3SO2Na is developed without the usage of transition-metal catalysts and external oxidants. This protocol features mild reaction conditions and wide functionality tolerance. Mechanistic insights indicate that the reaction proceeded via radical mechanism. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS Electrooxidative Annulation of Unsaturated Molecules via Directed C—H Activation Wucheng Xie, Xu Chen, Yunyue Li, Jieling Lin, Wanwen Chen, Junjun Shi Chinese Journal of Organic Chemistry 2022, 42 (5): 1286-1306. DOI: 10.6023/cjoc202110028 Published: 11 January 2022 Abstract (732) HTML (38) PDF (1031KB)(1489) Knowledge map Transition-metal catalyzed directed C—H bond activation and cyclization of unsaturated molecules have been developed as an efficient method to synthesize complex carbon aromatic and heteroaromatic compounds. However, additional stoichiometric oxidants are often required to realize the reoxidation cycle. Electrochemical organic synthesis can use current to replace expensive and toxic oxidants. It is an environment-friendly synthesis method. In recent years, remarkable progress has been made in the combination of electrochemical organic synthesis and C—H activation catalyzed by transition metals (such as Pd, Ni, Co, Ru, Cu, Rh, Ir, etc.). The latest progress of transition-metal catalyzed electrooxidative annulation of unsaturated molecules such as alkynes, olefins, carbon monoxide and isocyanogens via directed C—H activation is reviewed. Finally, the challenges and the future development on this important area are also described. Fig. & Tab. | Reference | Related Articles | Metrics Original article 2,2,6,6-Tetramethylpiperidinooxy (TEMPO)-Enabled Electrochemical Enantioselective Oxidative Coupling of Secondary Acyclic Amines with Ketones Ruimin Lu, Chang Guo Chinese Journal of Organic Chemistry 2022, 42 (1): 310-311. DOI: 10.6023/cjoc202200004 Abstract (569) HTML (21) PDF (476KB)(720) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Synthesis of gem-Difluoroalkenes through Nickel-Promoted Electrochemical Reductive Cross-Coupling Zhe Chang, Jiaxin Wang, Xi Lu, Yao Fu Chinese Journal of Organic Chemistry 2022, 42 (1): 147-159. DOI: 10.6023/cjoc202108006 Published: 15 September 2021 Online available: 15 September 2021 Abstract (1891) HTML (43) PDF (661KB)(1577) Knowledge map gem-Difluoroalkenes are important fluorine-containing compounds with structural superiority in organic synthetic chemistry and medicinal chemistry. For instance, the gem-difluoroethylene moiety could be converted to monofluoroalkenyl, difluoroalkyl, trifluoromethyl moiety, and many other fluorine-containing structures conveniently. The gem-difluoroethylene moiety is also an ideal carbonyl group bioisostere and has already been widely used in drug design. Herein, a nickel-promoted electrochemical reductive cross-coupling to access functionalized and substituted gem-difluoroalkenes is reported. This reaction enables the combination of allylic defluorination of trifluoromethyl alkenes and decarboxylation of redox-active esters or dehalogenation of alkyl halides under mild electrochemical reduction conditions and in an undivided cell, therefore obviates the use of stoichiometric amount metal powder or organic reductants. Furthermore, this reaction provides efficient access to biologically interesting molecules containing gem-difluoroethylene moiety. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics REVIEWS Research Progress of Photoelectric Co-catalysis Yingjie Liu, Zhichuan Wang, Jianping Meng, Chen Li, Kai Sun Chinese Journal of Organic Chemistry 2022, 42 (1): 100-110. DOI: 10.6023/cjoc202106051 Published: 03 September 2021 Abstract (1198) HTML (46) PDF (776KB)(1950) Knowledge map Photochemical and electrochemical reactions, which are mild and green, have been widely used in organic synthesis in recent years. To push the limits of both synthetic technologies, organic chemists have focused on using these two strategies to promote organic transformation in a single reaction system. A series of photoelectrochemical strategies have been developed, and the main one at present is electrochemically mediated photoredox catalysis. In addition, photoexcitation-assisted electroredox strategies have also gradually shown their potential in organic synthesis. These strategies realize the complementary advantages and disadvantages of photochemistry and electrochemistry, and can solve the problems that can not be solved by a single synthetic technology, such as removing oxidizing reducing agents that complicate the reaction, generating intermediates with high activity under mild conditions, and so on. In this paper, the research progress of photoelectrochemical strategies is summarized according to the existing photoelectric catalysis reactions, and the possible mechanism of some reactions is discussed. Fig. & Tab. | Reference | Related Articles | Metrics