Default Latest Most Read Please wait a minute... Visible-Light-Promoted Histidine-Specific Peptide C-H Alkylation Zhan Beibei, Shi Bingfeng Chinese Journal of Organic Chemistry 2019, 39 (12): 3602-3603. DOI: 10.6023/cjoc201900010 Abstract (548) PDF (423KB)(874) Knowledge map Reference | Related Articles | Metrics A Modular C-H Methylation Reaction via Catellani Strategy Tong Huarong, He Gang, Chen Gong Chinese Journal of Organic Chemistry 2019, 39 (11): 3306-3307. DOI: 10.6023/cjoc201900003 Abstract (715) HTML (14) PDF (417KB)(866) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Ketones and Aldehydes as Alkyl Radical Equivalents for Direct C-H Alkylation of Heteroarenes Cheng Xiaokai, Lu Zhan Chinese Journal of Organic Chemistry 2019, 39 (11): 3312-3313. DOI: 10.6023/cjoc201900006 Abstract (421) HTML (11) PDF (362KB)(709) Knowledge map Reference | Related Articles | Metrics Research Progress in Ligand-Assisted Copper-Catalyzed C-N Cross-Coupling Reaction in Aqueous Media or Pure Water Xie Jianwei, Wang Xiaochuang, Wu Fengtian, Zhang Jie Chinese Journal of Organic Chemistry 2019, 39 (11): 3026-3039. DOI: 10.6023/cjoc201907051 Published: 09 October 2019 Abstract (1228) HTML (45) PDF (819KB)(1304) Knowledge map Copper-catalyzed Ullmann-type C-N coupling reaction is one of the most effective methods to construct the C-N bonds. Water, as green and clean solvent, has been successfully employed in various organic reactions. According to the structure of ligands, the progress of ligand-assisted copper-catalyzed C-N cross-coupling reaction in aqueous media or pure water is summarized comprehensively, and the ligands include diamines, hydrazides, phenanthrolines, carbohydrates, pyridine-N-oxides, quinolines, oximes and salen. In addition, ligand-free copper-catalyzed C-N coupling reactions in aquous media or pure water are also reviewed. Fig. & Tab. | Reference | Related Articles | Metrics Recent Progress in Transition Metal-Free C-Heteroatom Bond Formation by Functionalization of C-H Bond in Imidazole-Fused Heterocycles Xu Xinming, Chen Demao, Wang Zuli Chinese Journal of Organic Chemistry 2019, 39 (12): 3338-3352. DOI: 10.6023/cjoc201904068 Published: 30 August 2019 Abstract (1145) PDF (836KB)(1231) Knowledge map Recently, the direct incorporation of heteroatom into imidazole-fused heterocycles through transition metal-free C-H functionalization has rapidly been advanced and become an eco-friendly synthetic tool for the synthesis of functionalized natural or bioactive molecules such as (hetero)arenes, olefins, carbonyl compounds. In particular, the C-H functionalization of imidazole-fused heterocycles has been considered to be the most important since it can lead to a new class of biologically active compounds. The recent progress in the incorporation of heteroatom into imidazole-fused heterocycles through transition metal-free C-H functionalization is introduced, and their mechanisms from a new perspective are also elaborated. Reference | Related Articles | Metrics Progress in Co-Catalyzed C-H Amination Sun Yiming, Ding Qifeng, Yu Yang, He Yide, Huang Fei Chinese Journal of Organic Chemistry 2019, 39 (12): 3363-3374. DOI: 10.6023/cjoc201906026 Published: 07 August 2019 Abstract (921) PDF (805KB)(1117) Knowledge map Amino compounds have a wide range of applications in the fields of organic chemistry, medicinal chemistry and functional materials. The efficient construction of C-N bonds has important research significance. Conventional amination reactions to construct C-N bonds require pre-functionalization of the substrate and inevitably produce quantitative halogenate by-products. The C-H amination reaction is directly based on hydrocarbons. The reaction has the advantages of "step" and "atomic" economy, in line with the green chemistry concept. Transition metal cobalt has the advantage of low toxicity and low cost. As a catalyst for C-H amination reaction, it exhibits its unique catalytic properties and attracts the attention of chemists. The research progress of cobalt-catalyzed C-H amination in recent years is summarized. At the same time, the challenges and development prospects of the research field are summarized and forecasted. Reference | Related Articles | Metrics Articles Carbazolation Study of Active Arenes with Carbazole-Containing Hypervalent Iodine(III) Reagents Lan Tianlei, Zhang Yue, Liu Wei, Xi Chanjuan, Chen Chao Chinese Journal of Organic Chemistry 2019, 39 (8): 2166-2174. DOI: 10.6023/cjoc201905050 Published: 17 July 2019 Abstract (1445) PDF (562KB)(1725) Knowledge map Carbazole and its derivatives are widely used in the field of medicine and photoelectric materials. A kind of stable cyclic hypervalent iodine reagents containing carbazole group was developed, which belong to benziodoxole compounds. In the presence of Cu(I) catalyst, these reagents reacted with aromatic substrates to give N-aryl carbazole derivatives. The reaction conditions are mild and suitable for a variety of electron-rich arenes. And a radical mechanism was proposed. Reference | Supporting Info. | Related Articles | Metrics Iron/O2-Promoted C-H Bond Functionalization for the Exclusive Synthesis of 2-Quinoline Carboxaldehydes under Microwave Irradiation Xie Tinghui, Jiang Xiaoying, Mi Zhisheng, Li Xue, Xu Xiaohe, Bai Renren, Shuai Qi, Xie Yuanyuan Chinese Journal of Organic Chemistry 2019, 39 (11): 3294-3298. DOI: 10.6023/cjoc201903007 Published: 09 July 2019 Abstract (636) HTML (10) PDF (429KB)(482) Knowledge map An one-pot iron-catalyzed oxidative formylation of 2-methylquinolines to produce 2-quinoline carboxaldehydes under microwave irradiation has been achieved by employing O2 as the oxygen donor. The reaction was general for the substrates with a wide range of functional groups, providing a yield of 48%~80%. The preliminary mechanistic studies revealed that the reaction underwent a radical pathway. Advantages of this method include the easy operation, short reaction time and good selectivity. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Recent Advances in Visible-Light-Induced Cross Dehydrogenation Coupling Reaction under Transition Metal-Free Conditions Kong Yaolei, Xu Wenxiu, Ye Feixia, Weng Jianquan Chinese Journal of Organic Chemistry 2019, 39 (11): 3065-3083. DOI: 10.6023/cjoc201905016 Published: 09 July 2019 Abstract (1605) HTML (63) PDF (1038KB)(3209) Knowledge map The cross dehydrogenation coupling reaction realizes direct coupling of two different X-H bonds to form a new chemical bond, thus featuring excellent step and atom economy. The traditional cross dehydrogenation coupling reaction was usually catalyzed by transition metal, which had the problems of expensive catalyst and serious pollution. Visible light-induced electron transfer is also an effective way to realize direct functionalization of X-H bonds. Visible-light-induced cross dehydrogenation coupling reaction under transition metal-free conditions is widely concerned due to the advantages of cleanliness, safety as well as high step and atom economy. Classified by the type of bonding, the research progress of these reactions is reviewed, and their future outlook is also discussed. Fig. & Tab. | Reference | Related Articles | Metrics Progress in Transition Metal Catalyzed C-H Functionalization Directed by Carboxyl Group Luo Feihua Chinese Journal of Organic Chemistry 2019, 39 (11): 3084-3104. DOI: 10.6023/cjoc201905027 Published: 09 July 2019 Abstract (1549) HTML (43) PDF (1082KB)(2227) Knowledge map The C-H activation assisted by directing groups is an important measure for selective C-H activation at specific positions, and it is also one of the hot spots in the research field of organic chemistry. As an efficient directing group, carboxylic acid has the advantages of low cost, low toxicity, easy modification and using as traceless directing groups. Recent development on C-H functionalization directed by carboxyl group according to different coupling modes is summarized, and the representative reaction mechanism is briefly described. Existing problems with a brief outlook in this field are also presented. Fig. & Tab. | Reference | Related Articles | Metrics Recent Advances in Copper-Catalyzed N-O Cleavage Strategy Lei Lu, Li Chengjing, Mo Dongliang Chinese Journal of Organic Chemistry 2019, 39 (11): 2989-3012. DOI: 10.6023/cjoc201904037 Published: 03 July 2019 Abstract (1894) HTML (53) PDF (1137KB)(2442) Knowledge map N-O bond cleavage is one of the most efficient and powerful strategies to introduce N-or O-functional groups into molecules in organic synthesis. Copper catalyst, as the abundant in earth and inexpensive advantages has been widely used to construct C-N and C-O bond. Furthermore, N-O bond cleavage has been successfully applied in the total synthesis of natural products and pharmaceuticals. The new development of copper-catalyzed N-O bond cleavage and its application in the total synthesis of natural products and pharmaceuticals in recent years have been summarized. Fig. & Tab. | Reference | Related Articles | Metrics Advances on Directing-Group Assisted meta-C-H Functionalization Catalyzed by Transition Metal Wu Mei, Huang Xinping, Zhang Haibing, Li Pengfei Chinese Journal of Organic Chemistry 2019, 39 (11): 3114-3131. DOI: 10.6023/cjoc201903029 Published: 19 June 2019 Abstract (1225) HTML (35) PDF (989KB)(1386) Knowledge map Transition-metal-catalyzed functionalization of unactivated C-H bonds is a highly attractive strategy for the synthesis of organic molecules, however, regioselective control is a central challenge in this field. The directing group assisted C-H functionalizations such as the use of directing templates and transient mediator, secondary interaction have attracted more attentions from researchers. The meta-C-H functionalizatioin assisted by directing groups are summarized in details. The existing problems and limitations of this field are also included. Finally, the development trend of this area is prospected. Fig. & Tab. | Reference | Related Articles | Metrics Palladium-Catalyzed Thiazole-Directed mono-Selective C(sp2)-H Bond Iodination Reaction Xing Lihao, Shao Lingyan, Fu Xiaopan, Deng Kezuan, Yang Jinyue, Ji Yafei Chinese Journal of Organic Chemistry 2019, 39 (11): 3154-3161. DOI: 10.6023/cjoc201904062 Published: 19 June 2019 Abstract (572) HTML (3) PDF (554KB)(855) Knowledge map A palladium-catalyzed ortho-C(sp2)-H bond iodination of 4-arylthiazoles has been developed. Through screening of directing groups and optimazation of reaction parameters, the most efficient reaction conditions for mono-ortho-position iodination were obtained, which were applied to synthesize a series of 4-(2-iodoaryl)thiazoles with broad scope of 4-aryl-thiazole substrates. Furthermore, the iodine group can be easily transformed into other organic functional groups, which improved the application value of this methodology. At last, plausible mechanism was proposed based on an intermolecular deuterium labeling kinetic experiment and radical inhibition experiments. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics NOTES Nickel-Catalyzed Coupling of 1,2-Diarylthio-1,2-diarylalkenes with Grignard Reagents for Synthesis of Multi-substituted Alkenes Wu, Yan, Luo, Fan, Pan, Shimin, Li, Yuhan, He, Shuhua Chinese Journal of Organic Chemistry 2019, 39 (10): 2946-2951. DOI: 10.6023/cjoc201904050 Published: 12 June 2019 Abstract (624) HTML (4) PDF (473KB)(720) Knowledge map A convenient protocol for the synthesis of multi-substituted alkenes from (Z)-1,2-diarylthio-1,2-diarylalkenes with Grignard reagents was developed via the highly selective coupling of (Z)-1,2-diarylthio-1,2-diarylalkenes catalyzed by 5.0 mol% NiCl2(dppe). The leaving organosulfur group could be converted to diaryldisulfide after hydrolysis and oxidation, which realized the recycling of sulfur resources, meeting the requirements of green chemistry. This process tolerated to different (Z)-1,2-diarylthio-1,2-diarylalkenes and Grignard reagents to deliver products in good to excellent yields, providing an efficient route to multi-substituted alkenes. Fig. & Tab. | Reference | Related Articles | Metrics REVIEW Advances on the Synthesis of Aryl Ethers via Dehydrogenative Coupling Tang Hao, Luo Junfei, Xie Pan Chinese Journal of Organic Chemistry 2019, 39 (10): 2735-2743. DOI: 10.6023/cjoc201904011 Published: 06 June 2019 Abstract (1357) HTML (19) PDF (768KB)(1046) Knowledge map Aryl ethers are important central motifs that are abundant in many natural products and drug molecules, as well as versatile building blocks for organic synthesis. Aryl ethers were usually synthesized through the coupling reactions between leaving group substituted arenes and alcohols. However, the introduction of leaving group requires extra synthetic operation and produces lots of wastes. Over the past decade, the method for the synthesis of aryl ethers via C—H alkoxylation or aryloxylation has received much attention due to its potential as an atom and step efficient methodology. Herein, the research advances on the synthesis of aryl ethers through dehydrogenative coupling are reviewed. The detailed substrate scopes and reaction mechanisms, as well as the limitations of current procedures and the prospects for the future, are discussed. Fig. & Tab. | Reference | Related Articles | Metrics Reviews Recent Advance in Transition-Metal-Catalyzed Silylation of C-H Bonds Huang Hongtai, Li Tao, Wang Jiazhuang, Qin Guiping, Xiao Tiebo Chin. J. Org. Chem. 2019, 39 (6): 1511-1521. DOI: 10.6023/cjoc201903078 Published: 28 May 2019 Abstract (1232) PDF (1536KB)(1803) Knowledge map Organosilicon compounds play an important role in pharmaceutical chemistry, material science and organic synthesis. Transition-metal-catalyzed direct silylation of C-H bond, as one of the most concise and efficient methods for the synthesis of organosilanes, has developed rapidly in recent years. In this paper, the recent advance in transition-metal-catalyzed silylation of C-H bonds since 2015 is mainly reviewed. Reference | Related Articles | Metrics Articles Asymmetric Synthesis of Axial Chiral Vinylarenes Fearturing Oxindole Moiety via Tandem Carbopalladation/C-H Olefination Yang Yun, Liu Huihui, Liu Xiaobing, Liu Tiantian, Zhu Yuqin, Zhang Anan, Wang Tao, Hua Yuanzhao, Wang Mincan, Mao Guoliang, Liu Lantao Chin. J. Org. Chem. 2019, 39 (6): 1655-1664. DOI: 10.6023/cjoc201903050 Published: 15 May 2019 Abstract (1076) PDF (1525KB)(1153) Knowledge map Due to the lower configuration stability of vinylarenes, arsing from the relatively lower rotational barriers, their catalytic asymmetric synthesis remains a daunting task. Oxindoles moiety are privileged framework of natural products and building blocks of bioactive molecules as well as pharmaceuticals. The asymmetric synthesis of axial chiral vinylarenes fearturing oxindole moiety via sequential carbopalladation/C-H olefination from readily available materials with palladium catalysis has been developed. (4R,5R)-(-)-2,2-Dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL)-derived phosphoramidite gave products with good yield and moderate ee value. The erosion of optical purity was not observed even after heating the product for 10 h at 110℃, which indicates the excellent stability of the chiral axial. Reference | Supporting Info. | Related Articles | Metrics Articles Chlorination of Anilide by Pd(OAc)2/N-Chloro-N-fluorobenzene- sulfonylamide Zhu Ye, Huang Jinwen, Yang Xianjin Chin. J. Org. Chem. 2019, 39 (6): 1665-1671. DOI: 10.6023/cjoc201903037 Published: 10 May 2019 Abstract (654) PDF (1174KB)(755) Knowledge map A mild method for palladium-catalyzed halogenation of acetanilide with N-chloro-N-fluorobenzenesulfonylamide (CFBSA) as a chlorinating reagent, oxidant, and novel promoting reagent was achieved. The decomposition of byproduct N-fluoroben-zenesulfonylamine in the presence of Pd(OAc)2 could accelerate the process of chlorination. Preliminary mechanism investigation showed that Pd catalyzed anilide directed C-H activation lead to the ortho chlorination selectivity. A series of ortho-chlorinated anilides were obtained in 28%~82% yields. Reference | Supporting Info. | Related Articles | Metrics Reviews Recent Advances on the Catalytic Functionalization of Quinoxalin- 2(1H)-ones via C-H Bond Activation Mao Pu, Zhu Junliang, Yuan Jinwei, Yang Liangru, Xiao Yongmei, Zhang Changsen Chin. J. Org. Chem. 2019, 39 (6): 1529-1547. DOI: 10.6023/cjoc201904025 Published: 06 May 2019 Abstract (918) PDF (1568KB)(1468) Knowledge map Quinoxalin-2(1H)-ones are very important N-heterocyclic moieties found in natural products and pharmaceuticals, and exhibit an amazingly wide spectrum of biological properties. Numerous efforts have been devoted to the development of efficient approaches for the C-H bond activation and functionalization of quinoxalin-2(1H)-ones in recent years, including alkylation, benzylation, acylation, arylation,amination, amidation, phosphonation, and fluoroalkylation. The recent advances in this area are summarized and their reaction mechanisms are discussed. Reference | Related Articles | Metrics Articles Nickel Chloride-Catalyzed Oxidation of Aromatic Hydrocarbon with Sodium Persulfate at the Benzylic Site Liu Lice, Wu Jieqing, Ma Hongfei, Zhang Han, Gu Jiefan, Li Yufeng Chin. J. Org. Chem. 2019, 39 (6): 1688-1694. DOI: 10.6023/cjoc201903003 Published: 26 April 2019 Abstract (870) PDF (1264KB)(931) Knowledge map A practical method for the oxidation of aromatic side chains was established for the preparation of aromatic aldehydes and ketones. Using NiCl2 as the catalyst, substituted toluenes were oxidized with Na2S2O8 at the benzylic site for the synthesis of the corresponding aldehydes in the yield of 22%~79%. Ethylbenzene analogs were oxidized more easily to obtain the corresponding ketones with 64%~84% yields. The oxidation of benzyl alcohol analogs was completed to acquire the corresponding carbonyl compounds in shorter time with better selectivity and yields. The method has the advantages such as the mild reaction conditions, no requirement for precious metals or additional promoter, and good selectivity. Reference | Supporting Info. | Related Articles | Metrics REVIEW Recent Advances in the α-C(sp3)-H Bond Functionalization of Glycine Derivatives Zhu Zhiqiang, Xiao Lijin, Xie Zongbo, Le Zhanggao Chin. J. Org. Chem. 2019, 39 (9): 2345-2364. DOI: 10.6023/cjoc201903006 Published: 26 April 2019 Abstract (1007) PDF (1001KB)(1720) Knowledge map α-Amino acids are the units of proteins, which not only widely occur in many biological important compounds and natural products, but also are useful as organic catalysts or ligands for asymmetric synthesis. Among them, glycines are particularly useful building blocks in organic synthesis. Direct C(sp3)-H bond functionalization of glycine derivatives provided an attractive synthesis strategy for the construction of a variety of α-substituted α-amino acids. The recent progress in the α-C(sp3)-H bond activation of glycine derivatives, with various reagents to form carbon-carbon and carbon-heteroatom bond, and oxidative coupling/cyclization reaction involving glycine derivatives is reviewed. Reference | Related Articles | Metrics REVIEW Recent Advances in Functionalization of Double Bond Based on Maleimides Yang Zhenhua, Zhu Jianan, Wen Caiyue, Ge Yingxiang, Zhao Shengyin Chin. J. Org. Chem. 2019, 39 (9): 2412-2427. DOI: 10.6023/cjoc201902012 Published: 19 April 2019 Abstract (2149) PDF (867KB)(1924) Knowledge map Maleimide, a common motif in a variety of natural alkaloids, has been extensively investigated due to its noteworthy biological activities and optical properties. Additionally, it can be transformed into many important heterocyclic frameworks such as succinimides, pyrrolidines, and 2-pyrrolidones. Thus, a great deal of attention has been focused on the development of new synthetic routes to access polyfunctionalized maleimides. In this article, the recent research progress in functionalization of double bond is reviewed based on maleimides according to Michael addition, oxidative coupling and cycloaddition reaction. Reference | Related Articles | Metrics Articles Copper-Catalyzed Aerobic Oxidative Coupling of Aromatic Sulfonyl Hydrazides with Amines:A New Access to Aromatic Sulfonamides Zhang Zhenlei, Qian Peng, Zha Zhenggen Chin. J. Org. Chem. 2019, 39 (5): 1316-1322. DOI: 10.6023/cjoc201903009 Published: 19 April 2019 Abstract (686) PDF (466KB)(626) Knowledge map A copper(Ⅱ)-catalyzed aerobic oxidative coupling of aromatic sulfonyl hydrazides with amines for the synthesis of aromatic sulfonamides was described. In contrast to previously described methods, this reaction employs copper/O2 as the catalytic system, and generates N2 as the only byproduct, which provides an environmentally benign synthetic route for aromatic sulfonamides. Reference | Supporting Info. | Related Articles | Metrics Reviews Recent Advances in the I2-Catalyzed C-H Bond Functionalizations Shi Zhaojiang, Wang Lianhui, Cui Xiuling Chin. J. Org. Chem. 2019, 39 (6): 1596-1612. DOI: 10.6023/cjoc201902001 Published: 11 April 2019 Abstract (803) PDF (1682KB)(1204) Knowledge map Heterocyclic compounds are widely applied in medicine, fine chemical engineering and the related industrial fields. Consequently, the development of efficient strategies for heterocycle constructions continues to be of great appeal in organic synthesis. In recent years, the I2-catalyzed direct C-H bond functionalizations have emerged as one of the most efficient synthetic protocols to construct diverse heterocycles. In this review, the recent advances in I2-catalyzed C-H bond functionalizations by the types of C-C and C-N/O/S bond formations are summarized, and an outlook of this research filed is given. Reference | Related Articles | Metrics Reviews Recent Advances in N-Phenoxyacetamides Directed C-H Bond Functionalizations Jiang Xiaolei, Hao Jiaqi, Zhou Guoqing, Hou Chengcheng, Hu Fangdong Chin. J. Org. Chem. 2019, 39 (7): 1811-1830. DOI: 10.6023/cjoc201902019 Published: 11 April 2019 Abstract (807) PDF (911KB)(1318) Knowledge map The C-H bond activation has become one of the hot fields of organic chemistry in recent years due to its atom economy and step simplicity. In the conventional C-H bond activations, an equivalent amount of oxidants is usually added to regenerate the catalyst and allow the catalytic cycle proceed smoothly. N-Phenoxyacetamide, as a novel reaction substrate containing an oxidizing directing group, can effectively avoid the use of an equivalent external oxidants. Thus, the C-H activation could be conducted under redox neutral conditions. In this paper, the latest research progress of N-phenoxyacetamides in the field of organic synthesis, especially C-H bond activations is reviewed, and the mechanism of the reaction is discussed. Reference | Related Articles | Metrics Notes Iodine-Catalyzed Telluration of Indole Derivatives with Diarylditellurides for Synthesis of 3-Aryltellurylindoles Chen Jinyang, Hu Li, Wang Haiying, Tan Honghui Chin. J. Org. Chem. 2019, 39 (7): 2048-2052. DOI: 10.6023/cjoc201812045 Published: 09 April 2019 Abstract (567) PDF (442KB)(535) Knowledge map In the presence of 20 mol% K2S2O8, a variety of 3-aryltellurylindoles were obtained in high yields via the telluration of indole dervatives with diarylditellurides catalyzed by 20 mol% I2. This process tolerates a wide spectrum of different indole derivatives and diarylditellurides. Other advantages include mild reaction conditions, high yields and atom economy, and an efficient route to 3-aryltellurylindoles is afforded. Reference | Supporting Info. | Related Articles | Metrics Articles Ruthenium-Catalyzed C(sp2)-H Alkenylation and Alkylation of 1-Benzyl-1H-pyrazole under Assistance of Pyrazole Group Xu Wentao, Wang Ning, Zhang Mengye, Shi Daqing Chin. J. Org. Chem. 2019, 39 (6): 1735-1742. DOI: 10.6023/cjoc201901005 Published: 21 March 2019 Abstract (490) PDF (1258KB)(824) Knowledge map A practical ruthenium-catalyzed C(sp2)-H alkenylation and alkylation of 1-benzyl-1H-pyrazole with alkene or a,β-unsaturated ketones under the assistance of pyrazole group were developed. This method has the advantages of high selectivity, providing only the ortho-alkenylation or ortho-alkylation products in high yields. This protocol provides an efficient and new method for the functionalization of 1-benzyl-1H-pyrazoles. Reference | Supporting Info. | Related Articles | Metrics Articles Copper-Promoted Direct Nitration of Arenes Assisted by an N,O-Bidentate Directing System Wang Yunlong, Zhang Linbao, Niu Junlong, Song Maoping Chin. J. Org. Chem. 2019, 39 (6): 1761-1766. DOI: 10.6023/cjoc201901015 Published: 08 March 2019 Abstract (635) PDF (1214KB)(640) Knowledge map Cu(Ⅱ)-promoted C-H nitration of arenes has been disclosed with the aid of N,O-bidentate directing group. The protocol was operationally simple by using NaNO2as the nitration source. Various amide substrates were tolerated in the reaction system, which establishes opportunities for developing simple and facile methods, and enriches the strategies to access aromatic nitro derivatives. Reference | Supporting Info. | Related Articles | Metrics Reviews Recent Advances in Direct C-H Bond Functionalization of Phenylalanine Derivatives Li Xiaofang, Xiong Weikang, Ding Qiuping Chin. J. Org. Chem. 2019, 39 (7): 1867-1874. DOI: 10.6023/cjoc201901029 Published: 08 March 2019 Abstract (946) PDF (574KB)(1569) Knowledge map Phenylalanine derivatives are widely found in a broad range of pharmaceutical molecules and exhibit significant biological activity. Direct C-H bond functionalization of phenylalanine derivatives to offer an efficient approach to construct C-I, C(sp2)-C(sp2), C(sp2)-C(sp), C(sp2)-C(sp3), C-N, C-B and C-O bonds is described. The transformation involves ortho-C-H bond iodination and the following intramolecular amination, ortho-alkylation, ortho-arylation, ortho-alkenylation, ortho-alkynylation, ortho-acylation, ortho-acetoxylation, ortho-amination, ortho-boronation, meta-arylation and meta-alky-lation. Reference | Related Articles | Metrics Notes Palladium-Catalyzed Dehydrative Cross Couplings of Stabilized Phosphorus Ylides with Allylic Alcohols Ma Xiantao, Yu Jing, Ma Ruitian, Yan Ran, Zhang Zhenlei Chin. J. Org. Chem. 2019, 39 (3): 830-835. DOI: 10.6023/cjoc201812051 Published: 22 February 2019 Abstract (690) PDF (503KB)(837) Knowledge map A dehydrative cross coupling of ketone-stabilized phosphorus ylides with the readily available allylic alcohols followed by an one-pot Wittig reaction is developed. A range of functional 1,4-dienes could be obtained in 52%~95% isolated yields in the presence of 5 mol% Pd(PPh3) 4 and 20 mol% B(OH) 3. The same method can be extended to ester or nitrile-stabi-lized phosphorus ylides, affording the corresponding 1,4-dienes in moderate yields. Reference | Supporting Info. | Related Articles | Metrics Articles Photoinduced Atom-Economical Iterative Hydrotrifluoromethylation of Terminal Alkynes and Remote C(sp3)-H Functionalization Liu Tao, Qu Chuanhua, Xie Jin, Zhu Chengjian Chin. J. Org. Chem. 2019, 39 (6): 1613-1622. DOI: 10.6023/cjoc201901021 Published: 19 February 2019 Abstract (1004) PDF (1241KB)(1057) Knowledge map Trifluoromethylation using Togni reagents usually releases one equivalent of iodobenzoats as wasteful byproducts. A visible-light-mediated, atom-and step-economical hydrotrifluoromethylation of aromatic alkynes and remote benzoyl-oxylation of α-C(sp3)-H bond of ether with Togni reagent as a bifunctional reagent by means of hydrogen atom transfer strategy was disclosed. The combination of two organic transformations into one reaction not only brings 100% atom economy but also addresses the challenge of stereoselective hydrotrifluoromethylation of aromatic alkynes. This unprecedented protocol offers an important access to a wide range of highly functionalized CF3-containing alkenes with great potential for post-modification. Reference | Supporting Info. | Related Articles | Metrics Articles Electrochemical Synthesis of Tetrasubstituted Hydrazines by Dehydrogenative N-N Bond Formation Feng Enqi, Hou Zhongwei, Xu Haichao Chin. J. Org. Chem. 2019, 39 (5): 1424-1428. DOI: 10.6023/cjoc201812007 Published: 18 January 2019 Abstract (1841) PDF (414KB)(1809) Knowledge map An electrochemical synthesis of tetrasubstituted hydrazines through dehydrogenative dimerization of secondary amines has been developed. The reactions are conducted in a simple undivided cell with constant current. The use of electricity to promote the reactions obviates the need for transition metal catalysts and oxidizing reagents, providing an efficient and sustainable access to tetrasubstituted hydrazines with diverse electronic properties. Reference | Supporting Info. | Related Articles | Metrics Articles Copper-Catalyzed Oxidative Cross-Coupling Reactions for the Synthesis of β-Acyl-α-amino Acid Derivatives in Aqueous Medium Zhou Anxi, Zhou Xiaofei, Mao Liuliang, Zheng Dagui, Zhu Xianhong, Chen Zongbao Chin. J. Org. Chem. 2019, 39 (4): 1070-1078. DOI: 10.6023/cjoc201809011 Published: 21 December 2018 Abstract (731) PDF (1323KB)(850) Knowledge map A novel copper-catalyzed oxidative cross-coupling reaction between N-arylglycine esters and Silyl enol ethers for the synthesis of β-acyl-α-amino acid esters has been developed. The features of this reaction are high reaction yields, mild reaction conditions (such as room temperature environments and inexpensive catalysts, etc.) and smooth operation in aqueous medium. Reference | Supporting Info. | Related Articles | Metrics Reviews Progress in Imine Formation from Direct Coupling of Alcohols and Amines Catalyzed by Metal Catalysts Wang Hui, Huang Longjiang Chin. J. Org. Chem. 2019, 39 (4): 883-902. DOI: 10.6023/cjoc201808039 Published: 05 December 2018 Abstract (864) PDF (925KB)(1664) Knowledge map Imines are very important class of compounds and have been widely utilized in fine chemicals, pharmaceuticals and chemical industry. The C=N double bond in imine is an important nitrogen source in different types of reactions due to its high reactive activity. Due to its high atom economy, catalytic direct coupling of alcohols and amines to imines based on metal catalysts has attracted much attention and maken great progress in recent years. In this paper, the advances in direct coupling of alcohols and amines to imines catalyzed by metal catalysts are reviewed. Reference | Related Articles | Metrics Reviews Progress in Copper-Catalyzed Chan-Lam Coupling of N-Compounds Duan Xiyan, Liu Ning, Wang Jia, Ma Junying Chin. J. Org. Chem. 2019, 39 (3): 661-667. DOI: 10.6023/cjoc201808015 Published: 26 October 2018 Abstract (1831) PDF (568KB)(2949) Knowledge map Construction of C-N bond is one of the most important areas in synthetic organic chemistry and medical chemistry. Many synthetic methods for the construction of C-N bond have been reported over the past few years. Copper-catalyzed Chan-Lam reactions represent one of the most powerful and straightforward tools to construct C-N bonds. In this paper, the recent progress in Chan-Lam coupling of N-compounds with (hetero) aryl boronates to construct C-N bond based on the reaction mechanism, reaction system, the scope of substrates, etc., is reviewed. Reference | Related Articles | Metrics Reviews Transition Metal-Catalyzed Regio-selective Aromatic C—H Bond Oxidation for C—O Bond Formation Yang Fanzhi, Zhang Han, Liu Xuri, Wang Bo, Ackermann Lutz Chin. J. Org. Chem. 2019, 39 (1): 59-73. DOI: 10.6023/cjoc201808017 Published: 26 October 2018 Abstract (2071) PDF (824KB)(1289) Knowledge map Recent years the great progress in transition metal-catalyzed direct aromatic C—H oxidation has been witnessed, which has been utilized in the preparation of various phenolic compounds. These transformations employ inter alia palladium, copper, ruthenium, iridium, etc. as the transition metal catalysts, and hypervalent iodine, persulfate, or oxygen as the oxidants. There have been several reviews in which the C—H oxidations with specific transition metal or oxidant was discussed. This review focuses specifically on transition metal-catalyzed aromatic C—H oxidations with ortho-, meta-, or para-selectivity, and rationalizes the possible generation mechanism of regio-selectivities, which might be controlled by the directing group via chelation-assistance, the ligand, or intrinsic properties of the substrate. The discussion section indicated the existing problems of transition metal-catalyzed aromatic C—H oxidations, as well as the possible limiting factors for the development and application of this strategy. Reference | Related Articles | Metrics REVIEW Recent Advances in Transition-Metal-Catalyzed Directing Group Assisted Nitration of Inert C-H Bonds Cheng Huicheng, Lin Jinlong, Zhang Yaofeng, Chen Bing, Wang Min, Cheng Lihua, Ma Jiaoli Chin. J. Org. Chem. 2019, 39 (2): 318-327. DOI: 10.6023/cjoc201807002 Published: 26 September 2018 Abstract (969) PDF (750KB)(1589) Knowledge map Aromatic nitro compounds are of great importance as chemical raw materials and organic synthesis intermediates. Traditional electrophilic nitration is difficult to achieve regioselective nitrification. In recent years, transition-metal-catalyzed C-H bond activation has developed rapidly. Most functional groups can be introduced into specific sites of aromatics through the chelation of transition metals with directing groups. Directing-group assisted C-H nitration, which is catalyzed by palladium, rhodium, ruthenium and other transition-metal, has made important progress due to its less byproducts, good regioselectivity and environmental protection. According to different transition metal catalysts, the research progress on transition-metal-catalyzed directing-group assisted C-H nitration is summarized, and the limitations of the research field and prospects for future develop-ment are presented. Reference | Related Articles | Metrics Cited: CSCD(1) ARTICLE Pd/1,3-Bis(diphenylphosphino)propane Catalyzed Arylation of Benzoxazoles at C-2 Position with Aryl Bromides Wang Yangdiandian, Yu Xiaojun, Fu Haiyan, Zheng Xueli, Chen Hua, Li Ruixiang Chin. J. Org. Chem. 2019, 39 (2): 482-490. DOI: 10.6023/cjoc201807050 Published: 10 September 2018 Abstract (579) PDF (1827KB)(792) Knowledge map A catalyst system combined of PdCl2 with 1,3-bis(diphenylphosphion)propane (dppp), which was simple and from commercially available materials, was reported for the highly efficient arylation of benzoxazoles at C-2 position with aryl bromides. This catalytic system could tolerate a great number of functional groups in benzoxazole and bromobenzene. With a low PdCl2 loading of 0.01 mol%, aryl bromides could be completely converted into the desired products for 24 h. If the loading of catalyst was up to 0.10 mol%, most of substrates could give more than 90% yields in 6 h. The exploration of the reaction mechanism discovered that Pd nanoparticles were formed during this reaction. The morphology and composition analysis of the Pd nanoparticles with transmission electron microscopy (TEM) and X-ray photoelectron spectroscopy (XPS) indicated that dppp played a key role to block the aggregation of palladium particles. In addition, the ring-opening pathway of benzoxazoles in the reaction process was proved by control experiments. Hot filtration experimental and high resolution mass spectrum (HRMS) analysis of filtrate suggested that the real active species were Pd(0)-Pd(Ⅱ)/dppp complexes. Reference | Supporting Info. | Related Articles | Metrics Articles Room Temperature Ru(Ⅲ)-Catalyzed ortho-Hydroxymethylation of Arenes Zhang Yong, Yang Zhongzhen, Yu Xinling, Cheng Xu, Li Weijian, Guo Lingmei, Hai Li, Guo Li, Wu Yong Chin. J. Org. Chem. 2018, 38 (12): 3211-3218. DOI: 10.6023/cjoc201805022 Published: 05 September 2018 Abstract (539) PDF (434KB)(520) Knowledge map Direct synthesis of the hydroxymethylated arene derivatives via ruthenium(Ⅲ)-catalyzed nitrogen atom directed C-H activation is described. The reaction proceeds smoothly at room temperature and generates the corresponding products in moderate to excellent yields. Meanwhile, it has a broad substrate scope and opens up an attractive avenue for the application of direct hydroxymethylation in the synthesis of biologically active compounds. Reference | Supporting Info. | Related Articles | Metrics Articles Direct C-H 3-Arylation of Quinoxalin-2(H)-ones with Aryl Diazonium Salts under Visible-Light Irradiation Wang Leilei, Bao Pengli, Liu Weiwei, Liu Sitong, Hu Changsong, Yue Huilan, Yang Daoshan, Wei Wei Chinese Journal of Organic Chemistry 2018, 38 (12): 3189-3196. DOI: 10.6023/cjoc201807014 Published: 22 August 2018 Abstract (1075) PDF (938KB)(1268) Knowledge map A simple and practical visible-light-induced protocol has been developed for the construction of 3-arylquinoxa-lin-2(1H)-ones via Eosin Y-catalyzed direct C-H 3-arylation of quinoxalin-2(H)-ones with aryl diazonium salts at room temperature in air. The present reaction provides a cost-effective and operationally straightforward approach to the target products in moderate to good yields, and does not require any metal reagents, bases, acids, and strong oxidants. Reference | Supporting Info. | Related Articles | Metrics page Page 1 of 2 Total 69 records First page Prev page Next page Last page