Default Latest Most Read Please wait a minute... Generation and Application of Iminyl Radicals from Oxime Derivatives Enabled by Visible Light Photoredox Catalysis Song Changhua, Shen Xu, Yu Fang, He Yupeng, Yu Shouyun Chinese Journal of Organic Chemistry 2020, 40 (11): 3748-3759. DOI: 10.6023/cjoc202004008 Published: 08 May 2020 Abstract (2701) PDF (1067KB)(2579) Knowledge map The advent of visible light photoredox catalysis has transformed the way of single-electron transfer (SET) processes and accessing radical species. As a result, the chemistry of nitrogen-centered radicals has witnessed a remarkable gain in interest. Specifically, under visible light photoredox catalysis, iminyl radicals can be generated from oxime derivatives, such as O-acyl oximes, O-aryl oximes and α-imino-oxy acids. Meanwhile, the reactivity of iminyl radcials is investigated systematically. Iminyl radicals can undergo four major classes of reactions, namely addition to arenes, intramolecular hydrogen atom transfer and subsequent reactions, addition to alkenes, Norrish type-I fragmentation (cleavage of α-carbon-carbon bonds) and subsequent reactions. In this review, the most significant progresses in the use of oximes and their derivatives as iminyl precursors are discussed and their engagement in photoredox-mediated transformations is outlined. Reference | Related Articles | Metrics Visible-Light Photoredox and Palladium Dual Catalysis in Organic Synthesis Zhou Wenjun, Jiang Yuanxu, Chen Liang, Liu Kaixing, Yu Dagang Chinese Journal of Organic Chemistry 2020, 40 (11): 3697-3713. DOI: 10.6023/cjoc202004045 Published: 29 May 2020 Abstract (2438) PDF (1077KB)(3433) Knowledge map Palladium-catalyzed organic transformations is an important branch of organometallic chemistry. Because it can efficiently construct carbon-carbon bonds and carbon-heteroatom bonds, palladium catalysis has been widely used in synthetic chemistry, material science and pharmaceutical industry. However, some of these reactions suffer from harsh reaction conditions, including high temperature and strong base. On the other hand, the visible-light photoredox catalysis employs the visible light as the energy source to generate highly reactive intermediates and realize many novel transformations, which are rare under the normal thermal reaction conditions, under mild reaction conditions. However, there are also limitations in reaction types and substrate scope in this field. In order to solve such problems in these two fields, organic chemists have merged the visible-light photoredox catalysis and palladium catalysis, realizing a series of novel organic transformations through the electron transfer or energy transfer between photosensitizer and organic palladium complex under mild conditions with high efficiency and selectivity, which has broad substrate scope and great application potential. In these transformations, visible-light photoredox catalysis and palladium catalysis both play their respective roles and cooperate well. The application of visible light photoredox and palladium dual catalysis in organic synthesis is summarized and the future research directions in this field are analyzed, which might help the further development of this field. Reference | Related Articles | Metrics REVIEWS Recent Advances in Visible-Light-Mediated Minisci Reactions Jianyang Dong, Yuxiu Liu, Qingmin Wang Chinese Journal of Organic Chemistry 2021, 41 (10): 3771-3791. DOI: 10.6023/cjoc202104024 Published: 02 June 2021 Abstract (2301) HTML (96) PDF (927KB)(2258) Knowledge map N-Heteroarenes are present in a wide variety of natural products, small-molecule drugs, organic materials, and ligands. Therefore, the methods for selective C—H functionalization of N-heteroarenes are highly sought-after for late-stage modification of pharmaceuticals. A useful tool for the synthesis of alkyl-substituted nitrogen-containing aromatic rings is the Minisci reaction, in which a protonated N-heteroarene is attacked by an alkyl radical under oxidative and acidic conditions. Classic Minisci reactions often require the use of excess oxidant, excess acid, and high temperature, which greatly limits the scope of the substrates. With the rapid development of photocatalysis in organic synthesis, in recent years, a variety of photocatalytic Minisci reactions have been reported, and successfully been applied to the synthesis of drugs. In this paper, the visible light mediated Minisci reactions in recent years are briefly reviewed. Fig. & Tab. | Reference | Related Articles | Metrics Photoinduced Decatungstate-Catalyzed C-H Functionalization Yuan Xiaoya, Yang Guoping, Yu Bing Chinese Journal of Organic Chemistry 2020, 40 (11): 3620-3632. DOI: 10.6023/cjoc202006068 Published: 09 September 2020 Abstract (2158) PDF (1456KB)(2549) Knowledge map In recent years, decatungstate [W10O32]4- as a catalyst has attracted much attention in the field of photocatalytic organic synthesis. With the catalysis of decatungstate, the C—H bond of substrate can be converted into the corresponding radical via a hydrogen atom transfer (HAT) progress under light irradiation. In this review, we summarized the recent advances of the application of decatungstate as a photocatalyst for the C—H functionalization to construct C—C, C—N, C—F bonds. Reference | Related Articles | Metrics REVIEWS Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate Baogui Cai, Jun Xuan Chinese Journal of Organic Chemistry 2021, 41 (12): 4565-4574. DOI: 10.6023/cjoc202109040 Published: 29 October 2021 Abstract (2013) HTML (77) PDF (766KB)(2276) Knowledge map Carbene is one of the most important synthetic intermediates in organic synthesis. In the past few decades, transition-metal catalyzed carbene transfer reactions have made remarkable development. Recently, visible light-promoted transformation of diazo compounds through the formation of free carbene as key intermediate begun to rise. The reaction only need visible light as the sole energy source which meets the concept of green chemistry. Since the pioneering works developed by the groups of Diaves and Zhou, photo-promoted transformation of diazo compounds has attracted more and more attentions. On the basis of previous work, the latest progress in this field is further improved, which mainly focuses on the recent new transformation reactions of diazo compounds under visible light irradiation and the contributions reported from Chinese research group. The future development direction, as well as challenges in this field is prospected. Fig. & Tab. | Reference | Related Articles | Metrics REVIEWS Advances of N-Hydroxyphthalimide Esters in Photocatalytic Alkylation Reactions Shuaiqi He, Haocong Li, Xiaolan Chen, Igor B. Krylov, Alexander O. Terent'ev, Lingbo Qu, Bing Yu Chinese Journal of Organic Chemistry 2021, 41 (12): 4661-4689. DOI: 10.6023/cjoc202105041 Published: 08 June 2021 Abstract (1901) HTML (61) PDF (1761KB)(2032) Knowledge map N-Hydroxyphthalimide (NHP) esters are easily available, stable, inexpensive, and highly photoactive compounds, which are derived from the corresponding carboxylic acids. In recent years, the application of NHP esters in photocatalytic decarboxylative reactions has captured huge attention. Herein, the vigorous development of photocatalytic alkylation reactions using alkyl NHP esters as alkylating reagents is summarized based on the classification of photocatalysts. Fig. & Tab. | Reference | Related Articles | Metrics REVIEWS Advances in Organic Photoelectrochemical Synergistic Catalysis Guang Yang, Yanwei Wang, Youai Qiu Chinese Journal of Organic Chemistry 2021, 41 (10): 3935-3947. DOI: 10.6023/cjoc202105054 Published: 06 July 2021 Abstract (1622) HTML (64) PDF (809KB)(1972) Knowledge map Following the renaissances of organic electrochemistry and photochemistry, photoelectrochemical approach was arising as one of hot research areas by combination advantages of photocatalysis and electrocatalysis. The photoeletrocatalysis was widely applied in redox reactions, coupling reactions and beyond. The development of photoelectrochemical transformations during past five years is summarized and the related reactions are classified according to mechanism and catalyst. The current progresses and future outlooks of such method are also discussed. Fig. & Tab. | Reference | Related Articles | Metrics Recent Advances in Transition Metal-Catalyzed Cross-Coupling Reactions Directly Promoted by Visible Light Li Zhenlong, Jin Jian, Huang Shahua Chinese Journal of Organic Chemistry 2020, 40 (3): 563-574. DOI: 10.6023/cjoc201910031 Abstract (1503) PDF (892KB)(2374) Knowledge map Over the last decades, the transition metal-catalyzed cross-coupling reactions have become powerful organic synthetic methods for forming carbon-carbon and carbon-heteroatom bonds. Very recently, the introduction of visible light into transition metal catalysis opened a new avenue for achieving novel, highly enabling cross-coupling reactions that otherwise were elusive. This type of reaction has received extensive attention due to its simple, mild conditions and no need of photocatalyst. Based on the classification of transition metals, the research progress of transition metal-catalyzed cross-coupling reactions directly promoted by visible light is reviewed. Reference | Related Articles | Metrics ARTICLES Selective Chlorination of Methane Photochemically Mediated by Ferric Chloride at Ambient Temperature Shangfei Huo, Hong Chen, Weiwei Zuo Chinese Journal of Organic Chemistry 2021, 41 (4): 1683-1690. DOI: 10.6023/cjoc202009044 Published: 10 December 2020 Abstract (1469) HTML (30) PDF (2530KB)(1053) Knowledge map Selective activation of methane under mild conditions to produce functionalized products is highly lucrative but remains challenging. The photochemical reaction of anhydrous ferric chloride (FeCl3) with methane at ambient temperature is an efficient process to selectively chlorinate methane to methyl chloride. An exclusive formation of methyl chloride instead of other multi-chlorinated products is observed, and a maximum initial productivity of 43 gMeCl?(kgFe?h)–1 was obtained under irradiation with a 300-watt high-pressure mercury lamp or solar light. Ferric chloride functions both as the source of reactive chlorine radicals and as the oxidant, and it was concomitantly reduced to ferrous chloride. The reaction rate increases with the power of the lamp and the concentration of ferric chloride. Interestingly, the reaction temperature from 25 to 75 ℃ and the methane pressure in the range of 1~4 MPa had little influence on the reaction rate. Methyl chloride was hydrolyzed to methanol with elimination of hydrogen chloride, and the ferrous product was re-oxidized to the ferric analog by oxygen in the air in the presence of hydrogen chloride, thus completing the loop of both iron and chlorine. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Recent Advances on the Photocatalytic and Electrocatalytic Thiocyanation Reactions Zhang Longfei, Niu Cong, Yang Xiaoting, Qin Hongyun, Yang Jianjing, Wen Jiangwei, Wang Hua Chinese Journal of Organic Chemistry 2020, 40 (5): 1117-1128. DOI: 10.6023/cjoc201912011 Published: 21 January 2020 Abstract (1445) PDF (820KB)(2083) Knowledge map Thiocyanate, as a versatile synthon, which has important application value in many fields such as pharmaceutical, pesticide and materials. The photocatalytic and electrocatalytic thiocyanation reactions have been widely concerned in organic chemistry due to the advantages of green, efficiency and safety. In this review, the cross-coupling/thiocyanation reactions based on the photocatalytic and electrocatalytic are described, which is expected to be helpful in exploring the green synthesis of thiocyanates compounds. Reference | Related Articles | Metrics REVIEWS Recent Progress in Radical Arylation Reaction with Diaryliodonium Salts under Photocatalysis Yuanyuan Sun, Jingcheng Song, Qixue Qin, Enxuan Zhang, Qingqing Han, Shaohui Yang, Zuli Wang, Shan Yue, Daoqing Dong Chinese Journal of Organic Chemistry 2021, 41 (12): 4651-4660. DOI: 10.6023/cjoc202106006 Published: 26 July 2021 Abstract (1414) HTML (30) PDF (706KB)(1306) Knowledge map Diaryliodonium salts have been widely applied in organic transformations. According to the reaction type, the use of diaryliodonium salts in visible light induced arylation reactions is summarized from the following three parts: C—C bond formation, C—S bond formation and C—P bond formation. Fig. & Tab. | Reference | Related Articles | Metrics Progress in Photoinduced Decarboxylative Radical Cross-Coupling of Alkyl Carboxylic Acids and Their Derivatives Zhou Mingdong, Qin Pitao, Jing Like, Sun Jing, Du Haiwu Chinese Journal of Organic Chemistry 2020, 40 (3): 598-613. DOI: 10.6023/cjoc201909030 Abstract (1401) PDF (954KB)(2610) Knowledge map Alkyl carboxylic acids are among the most ubiquitous organic molecules found in nature. The reactions using abundant carboxylic acid and its derivatives as starting materials deserve widespread attention over the world. They are often easy to generate alkyl radical by photoredox catalysis under mild conditions for building various chemical bonds in organic chemistry. Based on the reaction modes, decarboxylation of alkylcarboxylic acids and their derivatives, the recent progress in decarboxylation of alkylcarboxylic acids and their derivatives under visible light is reviewed. Reference | Related Articles | Metrics Progress on the Photocatalytic Organic Hydrogen-Evolution Coupling/Aromatization Reaction Chen Feng, Chen Hao, Wu Qing'an, Luo Shuping Chinese Journal of Organic Chemistry 2020, 40 (2): 339-350. DOI: 10.6023/cjoc201909024 Published: 01 November 2019 Abstract (1283) PDF (992KB)(2553) Knowledge map The photocatalytic redox reactions have been widely concerned in organic chemistry due to their green, efficiency and safety. In this review, the cross-coupling/aromatization reactions are described based on photocatalytic organic hydrogen-evolution, which can be used to build organic carbon-carbon and carbon-heteroatom bonds by using a photocatalyst/catalyst dual catalytic system. Hydrogen is the only by-product in these reactions. The system and catalytic mechanisms of organic photocatalytic redox reaction are highlighted. Reference | Related Articles | Metrics Visible-Light Promoted Hydroxylation of Aryl Halides under Mild Reaction Conditions in Neat Water Xu Xiuzhi, Zhang Fan, Huang Sheng, Zhang Zhiqiang, Ke Fang Chinese Journal of Organic Chemistry 2020, 40 (9): 2912-2918. DOI: 10.6023/cjoc202005004 Published: 17 July 2020 Abstract (1279) PDF (1026KB)(1280) Knowledge map A novel visible-light-introduced reaction for the construction of phenols via hydroxylation of aryl halides has been developed. The reaction has been achieved in high yield under mild conditions by using iodine as photocatalyst, which is cheap, easy to handle and environmentally friendly. A variety of phenols were obtained in up to 92% yields. Moreover, aryl chlorides were also successfully employed as substrates, affording the target phenols in good isolated yields. It might provide promising protocol for the synthesis of phenol derivatives. Its application was performed by the synthesis of 5-acetyl-4-hy-droxy-2-methoxybenzyl diisopropylcarbamodithioate, which displayed significant anti-proliferation effect. Reference | Supporting Info. | Related Articles | Metrics Review Application of α-Aminoalkyl Radical in Visible Light Catalysis He Zhao, Dongping Cheng, Xiaoliang Xu Chinese Journal of Organic Chemistry 2021, 41 (2): 642-660. DOI: 10.6023/cjoc202005055 Published: 09 September 2020 Abstract (1211) HTML (33) PDF (1110KB)(1303) Knowledge map Because of its low cost and environmental friendliness, visible light catalysis has been widely used in organic synthesis in recent years. Among them, α-aminoalkyl radical plays an important role because of its high activity and accessibility. The development and application of this active radical in visible light catalysis are mainly summarized and its outlook in the future is given. Fig. & Tab. | Reference | Related Articles | Metrics Porous Organic Polymers as Heterogeneous Catalysts for Visible Light-Induced Organic Transformations Xu Zi-Yue, Luo Yi, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting Chinese Journal of Organic Chemistry 2020, 40 (11): 3777-3793. DOI: 10.6023/cjoc202003070 Published: 30 April 2020 Abstract (1151) PDF (964KB)(1286) Knowledge map The recent applications of porous organic polymers (POPs) as heterogeneous catalysts for visible light-induced organic transformations are summarized. POPs are constructed from conjugated organic monomers, having the features of convenient synthesis and characterization, high stability for quick recovery and reuse, structural diversity as well as high modifiability. POPs possess rigid conjugated frameworks, relatively large surface areas, tunable porosity and typically insoluble in water or organic solvents, and thus ideal platforms for the development of heterogeneous catalysts. Through incorporating conjugated sensitizer units into the backbones or attaching the sensitizers to the backbone linkers, POPs can be developed as efficient heterogeneous photocatalysts for visible light-induced organic transformations. Due to their high stability and insolubility, POP catalysts can be easily recovered through filtration or centrifugation and recycled. POP-based photocatalysis combines visible light utility and catalyst recycling and thus represents a green and sustainable technique. Reference | Related Articles | Metrics Application of Iodine and Iodide in Photocatalysis Organic Synthesis Liu Yang, Lin Liqing, Han Yinghui, Liu Yingjie Chinese Journal of Organic Chemistry 2020, 40 (12): 4216-4227. DOI: 10.6023/cjoc202004053 Published: 28 June 2020 Abstract (1149) PDF (751KB)(1794) Knowledge map Photoredox catalysis has become a universal tool to catalyze a wide variety of chemical reactions with high selectivity under mild conditions. However, traditional photocatalysis relies heavily on photocatalysts with the problems such as high price and environmental pollution. Because iodine and iodide have the advantages of cheap, non-toxic and unique photoreactivity, their application in photochemical synthesis has attracted more and more attention in recent years. The research progress of photo-redox catalysis reactions mediated by iodine and iodide in recent years is summarized, and their future outlook is also discussed. Reference | Related Articles | Metrics Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex Chen Liang, Hu Liangjian, Du Yu, Su Weiping, Kang Qiang Chinese Journal of Organic Chemistry 2020, 40 (11): 3944-3952. DOI: 10.6023/cjoc202004041 Published: 19 May 2020 Abstract (1145) PDF (609KB)(853) Knowledge map A visible-light driven asymmetric Giese radical addition catalyzed by a bifunctional chiral-at-metal rhodium complex has been developed. para-Aminobenzyl radicals generated from para-aminophenylacetic acids could undergo a 1,4-addition in a highly enantioselective approach to α,β-unsaturated 2-acyl imidazoles, and a variety of corresponding adducts were obtained in moderate to high yields with excellent enantioselectivities. This reaction features high enantioselectivity, mild reaction conditions and an operationally simple procedure. A plausible reaction mechanism is proposed based on our research and literature precedents on dual functional chiral-at-metal catalysis. Reference | Supporting Info. | Related Articles | Metrics Visible-Light-Induced α-C(sp3)—H Amination Reactions of Tertiary Amines Zhao Yating, Zeng Junjie, Xia Wujiong Chinese Journal of Organic Chemistry 2020, 40 (1): 133-139. DOI: 10.6023/cjoc201907002 Published: 05 September 2019 Abstract (1119) PDF (599KB)(1177) Knowledge map Herein, the visible-light-induced α-C(sp3)—H amination reactions of tertiary amines were reported. By using readily available 1,3-dioxoisoindolin-2-yl benzoate as precursor of N-radical and blue LEDs as green and sustainable energy source, the α-C(sp3)—H bonds of various N,N-dimethylaniline derivatives were aminated directly. Based on radical trapping experiment and documented literature, a mechanism involving radicals coupling was proposed. This method featured in mild reaction conditions and good functional group tolerance, which provides a simple and practical protocol to the modification of tertiary amines. Reference | Supporting Info. | Related Articles | Metrics Recent Advances in Visible-Light-Promoted Transformation of Alkyl Boron Compounds Shi Dunfa, Wang Lu, Xia Chungu, Liu Chao Chinese Journal of Organic Chemistry 2020, 40 (11): 3605-3619. DOI: 10.6023/cjoc202006033 Published: 09 September 2020 Abstract (1112) PDF (961KB)(1397) Knowledge map Organoboron compounds are valuable synthetic intermediates and widely used in the synthesis of medicine, pesticide and organic optoelectronic materials due to their extensive resouce and highly transformable ability. Among various organoboron compounds, the synthesis and transformation of alkylboron compounds have attracted much attention. As a sustainable and green energy, visible light shows an important effect in organic systhesis. Tetracoordinated alkylboron compounds could occur single electron transfer (SET) process to generate alkyl radical for further transformations. Herein, the recent advances in the photoinduced transformation of alkyl boron compounds are summarized. Reference | Related Articles | Metrics Recent Progress of Photocatalytic Methylation of Arenes Du Jianbo, Chen Yuegang, Zuo Zhiwei Chinese Journal of Organic Chemistry 2020, 40 (11): 3646-3655. DOI: 10.6023/cjoc202006079 Published: 19 August 2020 Abstract (1086) PDF (920KB)(2012) Knowledge map Methylation of arenes is one of the versatile approaches to achieve structural modification in organic and medicinal chemistry. Installation of a methyl group onto an aromatic ring can lead to significant improvenent of the physical properties and biological activity of this molecule, thusly the effect oftentimes is called the“magic methyl effect”. During the past few years, visible-light-induced photocatalysis has emerged as a powerful tool for the development of efficient transformations in organic synthesis. Compared to traditional radical mediated reactions, the use of visible light as energy input is more environmentally benign. Recently, a series of aryl methylation reactions enabled by visible light photoredox catalysis have been reported and applied in the synthesis of pharmaceutically-interested products. In this review, the recent progress of visible-light-induced aryl methylation reactions is briefly summaried, with discussions of different reaction pathways. Reference | Related Articles | Metrics REVIEWS Application of α-Keto Acids in Metal-Free Photocatalysis Kunchen Xie, Mingxuan Jiang, Xiaolan Chen, Qiyan Lü, Bing Yu Chinese Journal of Organic Chemistry 2021, 41 (12): 4575-4587. DOI: 10.6023/cjoc202109008 Published: 21 October 2021 Abstract (1070) HTML (63) PDF (839KB)(1600) Knowledge map As a carboxylic acid, α-keto acid can be used as an acylating reagent by decarboxylation in organic synthesis. However, traditional methods often need transition metal catalysts or high temperatures, which limits the application of α-keto acid to a certain extent. In recent years, organic transformations induced by visible light have attracted extensive attention due to its mild conditions and simple operations. Herein, the recent advances of metal-free photocatalytic application of α-keto acids are summarized, which mainly include acylation reactions and cyclization reactions. Fig. & Tab. | Reference | Related Articles | Metrics HIGHLIGHT Visible-Light-Driven Sulfonamide Catalyzed Alkylation of α-C(3)—H Bonds of Heteroatoms Quanqing Zhao, Jiarong Chen Chinese Journal of Organic Chemistry 2021, 41 (2): 871-872. DOI: 10.6023/cjoc202100016 Abstract (1046) HTML (29) PDF (416KB)(1042) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics ARTICLES Sodium Iodide-Triphenylphosphine-Mediated Photoredox Alkylation of Aldimines Ziyan Shao, Qingli Zhou, Jiancheng Wang, Rui Tang, Yuehai Shen Chinese Journal of Organic Chemistry 2021, 41 (7): 2676-2683. DOI: 10.6023/cjoc202102039 Published: 29 April 2021 Abstract (1022) HTML (27) PDF (616KB)(708) Knowledge map The photoredox reactions involving electron donor-acceptor (EDA) complexes have attracted significant attentions in the last decade. Very recently, the sodium iodide-triphenylphosphine-N-acyloxyphthalimide EDA complex has been discovered and employed in developing several net redox-neutral photoreactions. Herein, the EDA complex has been applied in a net reductive setup for the first time to establish a photoredox alkylation of aldimines without photosensitizer. The reaction affords not only high yields for secondary, tertiary andα-heterosubstituted alkyl radicals, but also high yields for primary alkyl radicals, and moderate to high yields for electron-rich or secondary benzylic radicals, two difficult groups of radicals in previous studies. This work provides an efficient and reliable approach for the synthesis of unnatural amino acids and amines. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Visible-Light-Driven Photocatalytic Kharasch-Type Addition of 1,6-Enynes Fangzhou Geng, Shichao Wang, Kexian Song, Wenjuan Hao, Bo Jiang Chinese Journal of Organic Chemistry 2021, 41 (12): 4815-4824. DOI: 10.6023/cjoc202106014 Published: 20 July 2021 Abstract (1014) HTML (10) PDF (765KB)(697) Knowledge map A new visible-light-driven photocatalytic Kharasch-type addition of 1,6-enynes was reported. By using the characteristics of the in-situ-generation of trihalomethyl radicals from photocatalytic reduction of trichloromethane bromide and carbon tetrabromide, fac-Ir(ppy)3-catalyzed Kharasch-type addition of 1,6-enynes of these polyhalogenated hydrocarbon substrates at room temperature was conducted under visible-light irradiation, regioselectively affording 1-indanone derivatives with an exocyclic double bond and a quaternary carbon in moderate to good yields. Based on the experimental results and literature reports, a reasonable reaction mechanism was proposed, which involved the in-situ-generation of trihalomethyl radicals, radical-induced addition-cyclization and radical cross coupling. In addition, this protocol featured wide substrate scope, high functional group compatibility, 100% atomic utilization, and mild conditions as well as simple operation. It provides a green, mild, and efficient synthetic strategy for the construction of 1-indanone skeleton with potential application, which is consistent with the concept of green chemistry. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics HIGHLIGHTS Macrolactones via Photoinduced Ring Expansion of Cyclic Ketones Juntao Ye Chinese Journal of Organic Chemistry 2021, 41 (4): 1755-1756. DOI: 10.6023/cjoc202100030 Abstract (998) HTML (16) PDF (490KB)(660) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Coupling of Hantzsch Esters with Baylis-Hillman Derivatives via Visible-Light Photoredox Catalysis Chen Yuefeng, Zhao He, Cheng Dongping, Li Xiaonian, Xu Xiaoliang Chinese Journal of Organic Chemistry 2020, 40 (5): 1297-1304. DOI: 10.6023/cjoc201911024 Published: 15 February 2020 Abstract (971) PDF (534KB)(1102) Knowledge map 4-Alkyl Hasntzch esters are good alkyl radical storage. The preparation of multisubstituted α,β-unsaturated carboxylic acid esters under photocatalytic redox conditions by 4-alkyl Hantzsch esters and Baylis-Hillman adducts was investigated. The reaction conditions are mild and no additional additives are required. The coupling products were obtained in moderate to good yields. Reference | Supporting Info. | Related Articles | Metrics REVIEWS Application of Photochemical/Electrochemical Synthesis in C—H Functionalization of Quinoxalin-2(1H)-one Xiang Liu, Wen Li, Canzhan Zhuang, Hua Cao Chinese Journal of Organic Chemistry 2021, 41 (9): 3459-3481. DOI: 10.6023/cjoc202103032 Published: 08 June 2021 Abstract (968) HTML (50) PDF (1010KB)(1152) Knowledge map Quinoxalin-2(1H)-ones are a kind of important nitrogen-containing heterocyclic compounds, which have strong biological activity and chemical properties, and play an important role in synthesis chemistry, functional materials, drugs and so on. In recent years, the construction of 3-functionalized quinoxalin-2(1H)-one by C—H functionalization has attracted the attention of many scholars and made important progress. Among them, green chemistry oriented photocatalysis and electrochemical synthesis are becoming powerful tools for C—H functionalization of quinoxaline-2(1H)-one. In view of the great influence of photochemistry in synthetic chemistry, the research status of C—H functionalization of quinoxaline- 2(1H)-one in visible light catalysis and electrochemical synthesis is summarized, hoping to promote the further development of green synthesis strategy in the functionalization of nitrogen-containing heterocycles. Fig. & Tab. | Reference | Related Articles | Metrics Recent Advancement in Benzofulvene Synthesis Shi Chuanxing, Feng Chenguo, Chen Yali, Zhang Shusheng, Lin Guoqiang Chinese Journal of Organic Chemistry 2020, 40 (4): 817-830. DOI: 10.6023/cjoc201910029 Published: 03 January 2020 Abstract (966) PDF (925KB)(1577) Knowledge map Benzofulvenes were widely found in natural products and bioactive molecules, and also served as important building blocks in material science and transition-metal chemistry. Great efforts have been devoted to the efficient synthesis of these interesting molecules, and rapid advancement has been made in the past two decades. According to the types of the initiation of the reaction, these methods can roughly be classified into five categories:thermal or photochemical cyclization of enyne-al-lenes or enediynes, transition metal-catalyzed sequential cyclization reaction, electrophilic or nucleophilic attack initiated cyclization, radical initiated cyclization and acid promoted cyclization. This review describes the important synthetic methods of benzofulvenes according to their reaction types. Reference | Related Articles | Metrics REVIEWS Progress in Visible-Light Catalyzed C—F Bond Functionalization of gem-Difluoroalkenes Zhiqing Li, Xiaoyang Qiu, Jiang Lou, Qiang Wang Chinese Journal of Organic Chemistry 2021, 41 (11): 4192-4207. DOI: 10.6023/cjoc202106013 Published: 20 July 2021 Abstract (936) HTML (31) PDF (1074KB)(1265) Knowledge map Monofluoroalkene structural units widely exist in complex functional molecules such as drugs and natural products. They are also critical organic synthons with broad applications in medicine, biology, materials and other fields. Therefore, it is of great scientific significance and practical value to develop green, economical and efficient methods for synthesizing monofluoroalkenes. Functionalization of the C—F bond of gem-difluoroalkenes is an effective method to prepare monofluoroalkenes. The research progress in C—F bond functionalization of gem-difluoroalkenes under visible-light redox catalysis and visible-light redox/transition-metal synergistic catalysis, including the substrate scope, reaction mechanism, and synthesis applications, is summarized. Finally, the prospects of this reaction are also discussed. Fig. & Tab. | Reference | Related Articles | Metrics REVIEWS Application on the Construction of Imidazo[1,2-a]pyridines C-3 Canbon-Hetero Bonds by Visible-Light Catalysis and Electrochemistry Xiang Liu, Wen Li, Huanyu Liu, Hua Cao Chinese Journal of Organic Chemistry 2021, 41 (5): 1759-1773. DOI: 10.6023/cjoc202012026 Published: 07 February 2021 Abstract (935) HTML (45) PDF (877KB)(1418) Knowledge map Imidazo[1,2-a]pyridines are a special nitrogen-containing compounds, which play an important role in the fields of pesticides biomedicine, optical and electrical materials. In recent years, the synthesis of functional imidazo[1,2-a]pyridines has become a hot topic for organic scientists and pharmaceutical chemists, and great progress has been made. Among them, the synthesis of functionalized imidazo[1,2-a]pyridines via visible-light catalysis and electrochemistry based on green chemistry has become the powerful tool for the synthesis of these compounds. Based on the types of canbon-hetero bonds of imidazo- [1,2-a]pyridines, the research on the construction of imidazo[1,2-a]pyridines C-3 canbon-hetero bonds by visible-light catalysis and electrochemical synthesis in recent 5 years is summarized. Fig. & Tab. | Reference | Related Articles | Metrics REVIEWS Study on the Application of Photoelectric Technology in the Synthesis of Selenium-Containing Heterocycles Xin Wang, Yan Zhang, Kai Sun, Jianping Meng, Bing Zhang Chinese Journal of Organic Chemistry 2021, 41 (12): 4588-4609. DOI: 10.6023/cjoc202109046 Published: 21 October 2021 Abstract (878) HTML (36) PDF (1301KB)(1678) Knowledge map Selenium-containing heterocycles are a kind of important organic molecules, which are widely used in medicine, agrochemicals, organic materials and other fields. Therefore, the introduction of selenium atom into organic molecules is of great significance in synthetic chemistry. Visible light and electrochemical technology is one of the green and sustainable synthesis methods, which has opened up broad application prospects in the fields of bifunctionalization and cyclization of unsaturated bonds and direct functionalization of C—H bonds. In recent years, the development of novel selenium cyclization reaction using photoelectric technology to drive unsaturated bonds and direct selenization reaction of C—H bonds has attracted much attention. Therefore, this paper describes the electrochemical-driven and visible-light-induced synthesis reactions of selenium-containing heterocycles, and discusses the applicable scope and mechanism of some reactions. Fig. & Tab. | Reference | Related Articles | Metrics Visible-Light Promoted Preparation of Benzimidazoles by Eosin Y Catalyzed Reaction of Benzonitrile Derivatives in Water Lin Mei, Wu Fan, Liu Tianhui, Chen Zhitao, Xu Xiuzhi, Ke Fang Chinese Journal of Organic Chemistry 2020, 40 (8): 2563-2569. DOI: 10.6023/cjoc202004016 Published: 28 May 2020 Abstract (871) PDF (521KB)(827) Knowledge map A novel visible-light-introduced reaction for the construction of benzimidazole derivatives via radical cyclization of o-phenylenediamines with benzonitrile derivatives in water has been developed. The reaction has been achieved in high yield under mild conditions by using Eosin Y as photocatalyst, which is cheap, easy to handle and environmentally friendly. A variety of benzimidazoles were obtained in up to 91% yields. It might provide a promising protocol for the synthesis of benzimidazole derivatives. Reference | Supporting Info. | Related Articles | Metrics ARTICLES Visible Light-Mediated Metal-Free Decarboxylative Deuteration of Carboxylic Acid Yuhang He, Hui Yang, Dongxu Gao, Jiahui Ma, Yamin Shao, Guanghui An, Guangming Li Chinese Journal of Organic Chemistry 2021, 41 (12): 4725-4731. DOI: 10.6023/cjoc202111014 Published: 15 December 2021 Abstract (829) HTML (39) PDF (574KB)(619) Knowledge map A metal-free visible light-induced decarboxylation of phenylacetic acid derivatives has been successfully developed. Without the additives, direct decarboxylative monodeuteration of acids was successfully achieved using cheap deuterium sources. Besides, in presence of air, similar catalytic systems provided ketone products. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Visible Light-Induced Aldehyde Reductive Minisci Reaction towards N-Heterocycles Peng Sha, Lin Yingwu, He Weimin Chinese Journal of Organic Chemistry 2020, 40 (2): 541-542. DOI: 10.6023/cjoc202000006 Abstract (805) PDF (456KB)(1305) Knowledge map Reference | Related Articles | Metrics ARTICLES Visible-Light-Induced Benzylic C—H Oxygenation Reaction Using Tetrabutylammonium Tribromide as the Catalyst Pengcheng Dai, Liang Xu Chinese Journal of Organic Chemistry 2021, 41 (12): 4690-4695. DOI: 10.6023/cjoc202106041 Published: 19 August 2021 Abstract (803) HTML (25) PDF (548KB)(961) Knowledge map The direct oxidative functionalization of the benzylic C—H bonds of alkyl arenes paves a way for the quick synthesis of carbonyl compounds, which is of great significance in organic synthesis. In the past decades, the photooxidative pathways to achieve this reaction have developed rapidly, using relatively green and readily available oxygen as the terminal oxidant under light irradiation. In this paper, a commercially available and inexpensive chemical reagent, tetrabutylammonium tribromide (TBATB), was used to catalyze the photooxidation of the benzylic C—H bonds. Under visible light irradiation and air atmosphere, a catalytic amount of TBATB was utilized to achieve the efficient conversion of alkyl arenes to the corresponding aryl ketones. The reaction is feasible under mild conditions and without any additives, leading to a broad scope of ketone substrates. This method can be an effective supplement to the current benzylic photooxidation reaction systems. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics ARTICLES Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes Yu Liu, Zan Chen, Pu Chen, Biquan Xiong, Jun Xie, An Liu, Yun Liang, Kewen Tang Chinese Journal of Organic Chemistry 2021, 41 (6): 2290-2301. DOI: 10.6023/cjoc202102051 Published: 25 March 2021 Abstract (803) HTML (11) PDF (936KB)(742) Knowledge map A transition-metal-free visible-light-mediated tandem cyanoalkylsulfonylation/cyclization of alkynes with cycloketone oxime derivatives for the construction of 2-cyanoalkylsulfonyl-9H-pyrrolo[1,2-a]indoles through the insertion of SO2 is reported. The difunctionalization of carbon-carbon triple bonds includes a radical mechanism and undergoes the formation of iminyl radical, ring-opening of cycloketone, insertion of SO2, addition of sulfonyl radical to carbon-carbon triple bonds, intramolecular cyclization and isomerization. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics HIGHLIGHTS Photoredox-Catalyzed Iminoalkenylation of Alkenes for Diastereoselective and Stereodivergent Synthesis of 2-Cinnamylpyrrolines Xuesong Zhou, Jiarong Chen Chinese Journal of Organic Chemistry 2021, 41 (5): 2146-2147. DOI: 10.6023/cjoc202100037 Abstract (800) HTML (18) PDF (405KB)(798) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Visible-Light-Promoted Ir(III)-Catalyzed Z→E Isomerization of Monofluorostilbenes Zhang Qi-Qi, Lin Peng-Peng, Yang Ling, Tan Dong-Hang, Feng Si-Xin, Wang Honggen, Li Qingjiang Chinese Journal of Organic Chemistry 2020, 40 (10): 3314-3326. DOI: 10.6023/cjoc202005048 Published: 23 July 2020 Abstract (792) PDF (649KB)(827) Knowledge map A photocatalytic Z to E isomerization of monofluorostilbenes in the presence of visible light (blue LEDs) has been developed. The transformation, which proceeds through a selective energy transfer pathway with Ir(Ⅲ) complex, offers facile access to thermodynamically less stable E-monofluoroalkenes with synthetically useful efficiency (up to 96% yield, up to 91:9 E:Z). Mild reaction conditions, good functional groups tolerance, and broad substrate scope were observed. Furthermore, the synthetic utility of this method is demonstrated by the rapid synthesis of monofluorinated cis-DMU-212 analogue E-30. Reference | Supporting Info. | Related Articles | Metrics Tris(trimethylsilyl)silane/O2-Promoted and Photo-accelerated Conversion of Alkyl Iodides to Alcohols Li Jianyu, Zeng Jinlong, Chen Jianfeng, Zhao Baoguo Chinese Journal of Organic Chemistry 2020, 40 (11): 3853-3857. DOI: 10.6023/cjoc202006055 Published: 19 August 2020 Abstract (776) PDF (490KB)(515) Knowledge map A mild method for the conversion of alkyl iodides to alcohols was developed. The transformation was promoted by tris(trimethylsilyl)silane/O2 and accelerated by photoredox catalysis under visible light irradiation conditions. Various alkyl iodides, including primary, secondary and tertiary iodides, can be smoothly converted to the corresponding alcohols in 38%~99% yields. Reference | Supporting Info. | Related Articles | Metrics page Page 1 of 2 Total 72 records First page Prev page Next page Last page