Journals Publication Years Keywords Search within results ( AND 4J[Journal]) AND OR NOT Title Author Institution Keyword Abstract PACS DOI Please wait a minute... Choose Download reference EndNote Reference Manager ProCite BibTeX RefWorks Show/Hide thumbnails Select HIGHLIGHTS Asymmetric Synthesis of Trisubstituted Vicinal Diols through Copper(I)-Catalyzed Diastereoselective and EnantioselectiveAllylation of Ketones with Siloxypropadienes Jinlong Zhang, Gaoxi Jiang Chinese Journal of Organic Chemistry 2024, 44 (7): 2391-2392. DOI: 10.6023/cjoc202400039 Abstract (12) HTML (2) PDF (409KB)(9) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Select HIGHLIGHTS Catalytic Asymmetric Cascade Dearomatization of Indoles via a Photoinduced Pd-Catalyzed 1,2-Bisfunctionalization of Butadienes Daliang Tang, Feng Zhou, Jian Zhou Chinese Journal of Organic Chemistry 2024, 44 (7): 2389-2390. DOI: 10.6023/cjoc202400038 Abstract (13) HTML (2) PDF (404KB)(3) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Select HIGHLIGHTS Manganese-Catalyzed Asymmetric Hydrogenation of Ketimines with Minimally Different Alkyl Groups Mengfei Wang, Shiqi Jia Chinese Journal of Organic Chemistry 2024, 44 (7): 2387-2388. DOI: 10.6023/cjoc202400037 Abstract (10) HTML (3) PDF (426KB)(3) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Select HIGHLIGHTS Boryl Radical-Catalyzed Intra- and Intermolecular Cascade Radical Cyclization Reactions Yuan Liu, Honggen Wang Chinese Journal of Organic Chemistry 2024, 44 (7): 2384-2386. DOI: 10.6023/cjoc202400036 Abstract (10) HTML (2) PDF (368KB)(4) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Select HIGHLIGHTS Photoinduced 9-Flurenone Electron-Shuttle/Lewis Acid Cooperatively Catalyzed Enantioselective Radical Acylation and Alkylation of Aldimines Wenyuan Qu, Jiarong Chen Chinese Journal of Organic Chemistry 2024, 44 (7): 2381-2383. DOI: 10.6023/cjoc202400035 Abstract (10) HTML (1) PDF (384KB)(2) Knowledge map Fig. & Tab. | Reference | Related Articles | Metrics Select Study on Isolation, Identification and Bioactivity of Desferrioxamine E and Its Metal-Complexes from Streptacidiphilus jiangxiensis Jinda Li, Botao Cheng, Jiwu Huang, Wen Liu Chinese Journal of Organic Chemistry 2024, 44 (7): 2377-2380. DOI: 10.6023/cjoc202401038 Accepted: 10 April 2024 Abstract (51) HTML (2) PDF (927KB)(29) Knowledge map Research on the genus Streptacidiphilus was mainly focused on the isolation and identification of new species, with relatively less emphasis on the study of secondary metabolites. A new aluminium-complex alumioxamine (3), and two known compounds desferrioxamine E (1) and ferrioxamine E (2) were isolated from the fermentation broth of Streptacidiphilus jiangxiensis CGMCC 4.1857. Their structures were elucidated by MS, IR, NMR and single crystal X-ray diffraction technologies. Structurally, compound 3 features aluminum(III) as the central atom, which is bonded to six oxygen atoms of the ligand, forming a hexadentate complex. Furthermore, in vitro cytotoxicity assays showed that compound 1 exhibited potential inhibitory activity against four human tumor cell lines (Hela, PANC1, A375 and MHCC-97H) at a concentration of 100 μmol/L with cell viability ranging from 4.8% to 66.4%. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select Design, Synthesis and Herbicidal Activity of Novel Benzothiazole-Pyrimidinediones Compounds Baifeng Zheng, Yang Zuo, Qiong Chen, Qiongyou Wu Chinese Journal of Organic Chemistry 2024, 44 (7): 2371-2376. DOI: 10.6023/cjoc202311025 Accepted: 25 April 2024 Abstract (95) HTML (1) PDF (828KB)(100) Knowledge map Based on the benzothiazole-pyrimidinedione derivatives discovered in the our previous report, a series of novel pyrimidinedione derivatives with benzothiazole as the scaffold, which have not been reported in the literature, were designed and synthesized by the strategy of replacing sulfur bridge with oxygen bridge. All of the target compounds were evaluated for their herbicidal activity in the greenhouse assay at a dose of 150 g a.i./ha, and the results showed that some compounds exhibited good herbicidal activity against the tested six weeds. In particular, ethyl 2-((6-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoro- methyl)-3,6-dihydropyrimidin-1(2H)-yl)benzo[d]thiazol-2-yl)oxy)acetate (9ac) showed a broad-spectrum herbicidal activity with more than 85% efficacy against the weeds tested. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES o-Iodoarylation of Thiols Enabled by Aryne Generated from o-Diiodoarene and Sodium Hydride Dianfan Liu, Jianzhi Wang, Mengqing Wang, Xiaobei Chen, Yanwei Hu, Shilei Zhang Chinese Journal of Organic Chemistry 2024, 44 (7): 2363-2370. DOI: 10.6023/cjoc202312022 Accepted: 20 March 2024 Abstract (136) HTML (1) PDF (641KB)(145) Knowledge map A simple and efficient method is described for the synthesis of o-iodoaryl thioethers by the reaction of thiols and aryne. The aryne is generated from inexpensive and readily available reagents o-diiodoarene and sodium hydride. Remarkably, no disulfide substituted byproduct was observed in the reactions which is different from transition metal-catalyzed process. This method features simple operation, mild reaction conditions, broad substrate scope, and high reaction yields for many cases. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Asymmetric Total Synthesis towards the Simplified Analogs of Antibiotic Elansolid A Shuai Yang, Jie Wu, Liangliang Wang Chinese Journal of Organic Chemistry 2024, 44 (7): 2350-2362. DOI: 10.6023/cjoc202401017 Accepted: 21 March 2024 Abstract (132) HTML (2) PDF (600KB)(82) Knowledge map Natural product elansolid A belongs to one type of polyketide macrolactone with promising antibiotic activity. Previously, the first total synthesis of elansolid A in 28 longest linear sequence (LLS) and 41 steps in total has been achieved. Herein, the simplified analog of elansolid A, featured with a cyclohexyl-fused 19-memebered macrolactone, was proposed, and its asymmetric total synthesis based on a convergent strategy and key reactions exemplified by desymmetric alcoholysis of anhydride, Pd-catalyzed Stille coupling, Suzuki-Miyaura coupling as well as Mukaiyama macrolactonization was finished. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Copper-Based Solid Wastes Promoted Cross-Coupling Reactions of Terminal Alkynes Tong Xu, Ning Zhang, Yonghong Zhang, Bin Wang, Yu Xia, Weiwei Jin, Pinru Jin, Chenjiang Liu Chinese Journal of Organic Chemistry 2024, 44 (7): 2341-2349. DOI: 10.6023/cjoc202401012 Accepted: 28 March 2024 Abstract (102) HTML (1) PDF (1309KB)(62) Knowledge map An approach to the Sonogashira and Glaser-Hay coupling reactions utilizing copper-based solid wastes instead of traditional copper salts has been developed. This method enables the efficient synthesis of various disubstituted alkynes under relatively mild conditions. For the Sonogashira coupling reaction, diverse substituted phenylacetylenes and aryl iodides exhibit excellent reactivity, resulting in diaryl acetylene compounds with yields ranging from 57% to 97%. The Glaser-Hay coupling reaction allows for the high-yield production of symmetrically disubstituted 1,3-butadiyne derivatives using a variety of terminal alkynes. Additionally, moderate yields can be achieved for cross-coupling products. Gram-scale and cycling experiments demonstrate promising prospects for the application of solid waste in organic synthesis. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Manganese-Catalyzed Ring-Opening C—C Bond Fluorination of Cyclobutanols Limei Wang, Xiaoyuan Liu, Jincheng Zan, Shutao Sun, Lei Liu, Wei Li, Xigong Liu Chinese Journal of Organic Chemistry 2024, 44 (7): 2333-2340. DOI: 10.6023/cjoc202401031 Accepted: 28 March 2024 Abstract (53) HTML (3) PDF (507KB)(55) Knowledge map Manganese-catalyzed C—C bond cleavage of cyclobutanols has attracted great attention due to the high abundance and cheap and eco-friendly behaviour. A manganese-catalyzed ring-opening C—C bond fluorination of cyclobutanols is reported. Under mild conditions, the reaction provides a straightforward access to γ-fluorinated ketones using 10 mol% Mn(OAc)2 as catalyst and electrophilic fluorination reagent, which was generated in situ from HF•Et3N and PhIO, as fluorine source. The reaction has an excellent functional-group tolerance and displays a broad substrate scope, affording the corresponding products in 50%~76% yields. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES (4S,4'S)-2,2'-(4,6-Dibenzofurandiyl)bis[4,5-dihydro-4-phenyloxazole]-Ni(II) Complexes Catalyzed Highly Enantioselective Nitrile Imine Cycloaddition Reactions Xixian Cao, Jun You, Qiye Liu, Bo Liu, Yanchao Yu, Wenju Wu Chinese Journal of Organic Chemistry 2024, 44 (7): 2315-2332. DOI: 10.6023/cjoc202311029 Accepted: 28 March 2024 Abstract (131) HTML (2) PDF (893KB)(111) Knowledge map The Ni(II)-chiral (4S,4'S)-2,2'-(4,6-dibenzofurandiyl)bis[4,5-dihydro-4-phenyloxazole] (DBFOX/Ph)-catalyzed asymmetric 1,3-dipolar cycloadditions of nitrile imines to N-α,β-unsaturated acylpyrazoles was presented. This tactic rendered a facile and feasible route to prepare the optically active tetrasubstituted 5-3,5-dimethylpyrazole acyl dihydropyrazole cycloadducts bearing one or two contiguous stereocenters in good yields (up to 97% yield) with high regioselectivities (100%) and enantioselectivities (up to 97.5% ee). Following that, chiral cycloadducts could be obtained consistently in good chemical yields with excellent enantioselectivities within the gram scale process, additionally, toward five kinds of derivatization reactions like nucleophilic and reduction for further conversion of chiral cycloadducts to related chiral dihydropyrazole derivatives encompassing different substituents. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Synthesis and Anti-neuroinflammatory Activities of 25-Hydroxycholesterol and Its Analogues Liusong Lan, Qian Yang, Yongyi Li, Shujun Fang, Yuxuan Huang, Juncheng Su, Chengxue Pan, Guifa Su Chinese Journal of Organic Chemistry 2024, 44 (7): 2305-2314. DOI: 10.6023/cjoc202312002 Accepted: 10 April 2024 Abstract (121) HTML (2) PDF (858KB)(114) Knowledge map 25-Hydroxycholesterol (25HC) has many important biological activities and is also a key intermediate for the synthesis of calcifediol, calcitriol, etc. It is of great significance to develop a new synthetic route which is easy to available raw materials, simple process, and easy to scale up. In this report, three 25-hydroxycholesterol and its analogues were synthesized from hyodeoxycholic acid via esterification of hydroxyl groups, decarboxylation iodization of carboxyl groups, ketonic hydrolysis after nucleophilic substitution with α-ketoester, sulfonate esterification then elimination, and finally reaction with Grignard reagent. The total yield was 20.8%~23.0%. The new route is simple to operate and easy to scale up, and is expected to be further developed into an industrial synthetic route. Similar analogues of 25-hydroxycholesterol can be easily prepared by changing α-ketoesters and Grignard reagents. Among the 15 compounds synthesized, there are 9 new compounds. Their biological activities were evaluated. The results showed that 26,27-diethylcholest-5-ene-3β,25-diol (8c) has good anti-neuritis activity and can inhibit NO release from LPS (lipopolysaccharides)-induced BV-2 (mouse microglia) cells by inhibiting Nuclear Factor kappa-B (NF-κB) and Mitogen-activated protein kinase/c-Jun N-terminal Kinase (MAPK/JNK) signaling pathways, and down-regulating mRNA-levels of inflammatory cytokines such as Interleukin-6 (IL-6), Tumor Necrosis Factor-α (TNF-α) and Interleukin-1β (IL-1β), indicating that 8c is a potential anti-neuroinflammatory compound. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Semi-synthesis of Glycosylated Interferon-γ Minyuan Zhou, Jie Zhao, Farong Ye, Ping Huang, Minggang Deng, Ping Wang Chinese Journal of Organic Chemistry 2024, 44 (7): 2296-2304. DOI: 10.6023/cjoc202402006 Accepted: 10 April 2024 Abstract (60) HTML (1) PDF (1149KB)(72) Knowledge map Interferon-gamma (IFN-γ) is an important cytokine with enhanced immune activity, anti-tumor and antiviral effects, and holds significant potential in medical research and clinical applications. In this study, we report a highly efficient semi-synthesis strategy of homogeneous N-GlcNAc modified IFN-γ. The glycopeptide fragment (Pyr1-Leu33) and peptide fragment (Lys34-Ser39) were prepared through chemical methods. And the peptide fragment (Ser40-Gly138) was obtained through Escherichia coli (E. coli) expression. Subsequently, using a combination of “expressed serine ligation” and “native chemical ligation-desulfurization”, we ligated these fragments from the C-terminal to the N-terminal, resulting in a full-length glycoprotein, which was successfully refolded to obtain the desired product. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines Yucai Tang, Yupeng He, Biyu Yang, Jinglin Duan, Changyuan Du, Jie Jiang, Jiali Li, Ruohan Pan, Yu Chen, Xuewen Liu Chinese Journal of Organic Chemistry 2024, 44 (7): 2286-2295. DOI: 10.6023/cjoc202401034 Accepted: 10 April 2024 Abstract (68) HTML (2) PDF (960KB)(109) Knowledge map An efficient visible-light-induced radical cascade azidation/cyclization of 2-aryl indoles with trimethylsilyl azide (TMSN3) has been developed using organic dye Rose Bengal as the photocatalyst. This method did not require metal catalysts and additives, and used air as the oxidant to obtain diverse indolo[2,1-a]isoquinolin-6(5H)-ones in moderate to good yields. Mechanistic studies demonstrated that the reaction proceeded via a radical pathway. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Cascade Cross-Coupling/[3,3]-Sulfonium Rearrangement of Alkynyl Sulfoxides and Ynamides/Ynol Ethers to Construct Tetrasubstituted Furans Shuyu Meng, Wentao Guo, Quanrui Wang Chinese Journal of Organic Chemistry 2024, 44 (7): 2274-2285. DOI: 10.6023/cjoc202401016 Accepted: 10 April 2024 Abstract (94) HTML (2) PDF (773KB)(131) Knowledge map A transition-metal-free strategy for the synthesis of tetrasubstituted furans is reported. Promoted by boron trifluoride diethyl etherate, the reaction of alkynyl sulfoxides with ynamides/ynol ethers proceeded via a cascade process including cross-coupling of the two reactants, [3,3]-sulfonium rearrangement, and 5-exo-dig heterocyclization, leading to tetrasubstituted furan products. The resultant α-alkylthio groups can be used for further functionalization, such as to introduce other alkyl/aryl groups. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Visible-Light Induced Iron-Catalyzed Hydroxymethylation of N-Heterocycles Yanhua Fu, Chang Xu, Chao Zhang, Yisha Wang, Gaofeng Feng Chinese Journal of Organic Chemistry 2024, 44 (7): 2265-2273. DOI: 10.6023/cjoc202312025 Accepted: 10 April 2024 Abstract (124) HTML (1) PDF (586KB)(124) Knowledge map A new strategy for iron-catalyzed visible-light induced hydroxymethylation of N-heterocycles with methanol under mild conditions was developed. By employing FeCl3 as the catalyst, 2-methylisonicotinic acid as the ligand, TsOH as the acid, air as the oxidant, and aqueous MeOH as the solvent, varieties of substituted quinolines, isoquinolines, pyridines, benzothiazole and voriconazole were hydroxymethylated smoothly in good to excellent yields, exhibiting good substrate scope. This strategy features green reaction conditions, excellent atom-economy and simple operations. It has potential applicable value in late-stage structure modification of drug molecule. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Design and Application of a Novel Chalcone Derivative Fluorescent Probe for Aminopeptidase N Yiran Hu, Siliang Zhang, Haiyan Luo, Luyao Zhao, Xudong Guo, Shuangqing Wang, Rui Hu, Guoqiang Yang Chinese Journal of Organic Chemistry 2024, 44 (7): 2257-2264. DOI: 10.6023/cjoc202312029 Accepted: 10 April 2024 Abstract (75) HTML (1) PDF (1035KB)(54) Knowledge map Aminopeptidase N (APN) is a widely expressed hydrolytic enzyme in organisms that can hydrolyze neutral or alkaline amino acids at the N-terminus of protein polypeptide chains. Overexpressed APN may indicate disorders of biosystems, such as various tumors, drug-induced liver injury (DILI), and glomerulonephritis, and is widely used for early diagnosis and therapy of related diseases. Particularly, elevated APN level in urine is becoming one of the key markers of early kidney injury due to its special sensitivity to glomerulonephritis than other proteins. Herein, based on the structure of 4-amino chalcone, a novel fluorescent probe Ala-OMN for detecting APN was designed and synthesized by caging the 4-amino of OMN by alanine. Ala-OMN is non-fluorescent in phosphate buffered saline (PBS). After reaction with APN, the caging group alanine was hydrolyzed and OMN was released, which further combined with bovine serum protein (BSA) to form a 1∶1 complex, concomitantly with a bright green fluorescence signal for indicating APN. Ala-OMN exhibits excellent sensitivity, selectivity, and anti-interference ability in response to APN, with a detection limit as low as 0.058 ng/mL. Ala-OMN has been successfully applied to detect APN concentration in urine samples, and the results are in good agreement with commercial reagent kits, suggesting that Ala-OMN could be a new diagnostic reagent for the clinical detection of early glomerulonephritis. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Synthesis of 3,5-Diaryl-1,2,4-oxadiazole by One-Pot Homocoupling Reaction Mengjin Liu, Yan Xiao, Kai Zhou, Zicheng Li, Wencai Huang Chinese Journal of Organic Chemistry 2024, 44 (7): 2251-2256. DOI: 10.6023/cjoc202401030 Accepted: 25 April 2024 Abstract (46) HTML (1) PDF (431KB)(42) Knowledge map 3,5-Diaryl-1,2,4-oxadiazoles were synthesized by homocoupling of chloroarylaldoxime from arylaldoxime and N-chlorosuccinimide (NCS) in the presence of Cs2CO3 in one pot. The method is suitable for thiophene-3-carbaldehyde, isonicotinaldehyde and arylaldehyde without active substituent with a yield from 19% to 78%. However, it was not suitable for aliphatic aldehydes, other heteroaromatic aldehydes and benzaldehydes carrying active groups (hydroxyl, amino and carboxylic acid). Compared to reported methods, this method uses only aromatic aldoxime as a single substrate. The process is simple, convenient, and green, making it a reliable way to synthesize 3,5-(homo-substituted)-1,2,4-oxadiazoles. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES One Pot Tandem P-Michael Addition/SN2/Intramolecular Wittig Reaction of aza-o-Quinone Methides: Construction of 2,3-Disubstituted Dihydroquinoline Derivatives Yudi Liu, Hang Cheng, Zhaolin He, Wei Chen Chinese Journal of Organic Chemistry 2024, 44 (7): 2241-2250. DOI: 10.6023/cjoc202402002 Accepted: 25 April 2024 Abstract (63) HTML (2) PDF (743KB)(60) Knowledge map A one-pot tandem P-Michael addition/SN2/intramolecular Wittig Reaction of in situ generated aza-o-quinone methides with PPh3 and α-bromo ketones has been reported. This protocol provided an efficient and mild approach to synthesize 2,3-disubstituted dihydroquinolines in 25%~93% yields. In addition, the 2,3-disubstituted quinolines could also be obtained by simply modification of the reaction conditions. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Ag(I)-Catalyzed Addition of Cyclopropenones and Alcohols via C—C Bond Cleavage Shulin Zhang, Zhou Zhang, Meng Sun Chinese Journal of Organic Chemistry 2024, 44 (7): 2233-2240. DOI: 10.6023/cjoc202403007 Accepted: 25 April 2024 Abstract (87) HTML (2) PDF (524KB)(155) Knowledge map An efficient method for the synthesis of α-phenylcinnamates via silver catalyzed C—C bond activation reaction of cyclopropenone and alcohol was developed. This protocol features a simple reaction system, specific regioselectivity, good functional group compatibility and good yields. It is of great significance for the later modification of natural products. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Synthesis of Spiropyrans via Rh(III)-Catalyzed [3+3] Cyclization of 3-Aryl-2H-1,4-benzoxazine and Diazonaphthalene-2H-ones Mengke Wen, Yiyue Li, Haokang Du, Zhangpei Chen, Xifa Yang Chinese Journal of Organic Chemistry 2024, 44 (7): 2223-2232. DOI: 10.6023/cjoc202403012 Accepted: 25 April 2024 Abstract (51) HTML (1) PDF (681KB)(46) Knowledge map Rh(III)-catalyzed 1∶1 coupling of 3-aryl-2H-benzo[b][1,4]oxazines with diazonaphthalene-2H-ones has been realized for mild synthesis of NH-containing spiropyrans. The reaction proceeded via C—H activation followed [3+3] annulation with decent functional group tolerance. Preliminary mechanistic studies have been conducted and a plausible mechanism has been proposed. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select ARTICLES Metal-Free 1,8-Diazabicyclo(5.4.0)-undec-7-ene Mediated Synthesis of α-Acetal Amides through Reaction of Glyoxylic Acid Acetalde with Aryl Isothiocyanates Rou Ding, Siyu Shi, Chao Ma, Wei Wei, Yufen Lü Chinese Journal of Organic Chemistry 2024, 44 (7): 2216-2222. DOI: 10.6023/cjoc202403029 Accepted: 30 April 2024 Abstract (66) HTML (3) PDF (583KB)(43) Knowledge map Metal-free condensation reaction of glyoxylic acid acetalde with aryl isothiocyanates leading to α-acetal amides has been reported. The present protocol, which simply utilizes 1,8-diazabicyclo(5.4.0)-undec-7-ene (DBU) as base, provides a green and efficient approach to construct a series of α-acetal amides in the absence of metal catalysts and stoichiometric amounts of coupling reagents. Fig. & Tab. | Reference | Supporting Info. | Related Articles | Metrics Select REVIEWS N-Heterocyclic Carbene Catalyzed the Umpolung of Aldehyde Compounds Ming Zhao, Rui Yan, Hu Chen Chinese Journal of Organic Chemistry 2024, 44 (7): 2204-2215. DOI: 10.6023/cjoc202401009 Accepted: 20 March 2024 Abstract (107) HTML (1) PDF (852KB)(263) Knowledge map Aldehyde compounds are a class of important organic compounds, which are widely used in organic synthesis. The typical reaction of aldehydes is the addition reaction with various nucleophiles as electrophiles. However, the electrophilicity of aldehyde carbonyl group limits the further application and development of aldehydes in synthesis. Since chemists discovered that cyanogen ions can change the reaction polarity of benzaldehyde, the strategy of umpolung has attracted much attention. N-Heterocyclic carbene (NHC) is a kind of important small organic molecule catalyst, which plays a key role in the field of organic catalysis. A series of important advances have been made in the study of the umpolung of aldehyde compounds catalyzed by NHC. The umpolung of aldehydes catalyzed by NHCs is introduced, and the positions of carbon atoms and the reactions of umpolung are summarized with the purpose of attracting much attention to this research field, and the development of new models and reactions within NHC catalysis. Fig. & Tab. | Reference | Related Articles | Metrics Select REVIEWS Advances in the Synthesis of Mono/Di/Polyfluoroalkyl Ethers Dongxue Song, Hongqiong Zhao, Ying Xu, Chenfeng Ji, Yingjie Liu Chinese Journal of Organic Chemistry 2024, 44 (7): 2174-2203. DOI: 10.6023/cjoc202401003 Accepted: 20 March 2024 Abstract (93) HTML (4) PDF (1522KB)(124) Knowledge map Fluoroalkyl ethers are widely used in organic chemistry, materials science, environmental science, life science and other fields, especially in biopharmaceuticals, where the introduction of fluoroalkoxy groups has attracted much attention for their ability to improve metabolic stability and cell membrane permeability, thus significantly improving the pharmacodynamic and pharmacokinetic properties of biologically active molecules. Although several strategies for the construction of fluoroalkyl ethers have been reported, the number of fluoroalkyl ether-containing drugs and agrochemicals on the market is still small. Therefore, the development of effective methods for the preparation of fluoroalkyl ethers is a much needed and challenging task. The progress of research on the synthesis of monofluoromethyl ethers, difluoromethyl ethers, and polyfluoroalkyl ethers is categorized and summarized, mainly in terms of C—O bond-coupled indirect fluoroalkoxylation, C(sp2)—H, C(sp2)—C, C(sp3)—X (heteroatom) direct fluoroalkoxylation and other direct fluoroalkoxylation. The possible mechanisms and applicability of some reactions are also discussed. Fig. & Tab. | Reference | Related Articles | Metrics Select REVIEWS Vinylene Carbonate: A Versatile Synthon in Organic Synthetic Chemistry Yu Lin, Haifeng Fu, Hua Cao, Xiang Liu Chinese Journal of Organic Chemistry 2024, 44 (7): 2147-2173. DOI: 10.6023/cjoc202401036 Accepted: 28 March 2024 Abstract (117) HTML (3) PDF (1279KB)(150) Knowledge map In recent years, vinylene carbonate has become a new and ideal multifunctional synthon, which is widely used in a variety of organic transformations. Especially in the field of transition metal-catalyzed C—H functionalization, it can be used to construct target molecules containing carbon and heterocyclic skeletons. Since Nishii and Miura first reported that vinylene carbonate participates in coupling reactions as an “ethynol surrogate” in 2009, it has been successively reported as an “acetylene surrogate”, “C1 synthon”, “acylmethylation reagent”, and others. These developments not only highlight the multifunctional transformation of vinylene carbonate, but also provide new ideas for the synthesis of complex compounds. The latest research progress of vinylene carbonate in recent years is summarized and the prospects for its future development based on the different reaction roles of vinylene carbonate in synthetic chemistry are proposed. Fig. & Tab. | Reference | Related Articles | Metrics Select REVIEWS Recent Advances of Minisci Reactions in Aqueous Solution Wengui Wang, Shoufeng Wang Chinese Journal of Organic Chemistry 2024, 44 (7): 2136-2146. DOI: 10.6023/cjoc202401015 Accepted: 28 March 2024 Abstract (93) HTML (1) PDF (698KB)(79) Knowledge map Minisci reaction is a convenient method for the functionalization of C—H in electron-defficient N-heterocycles. Different substituents could be introduced onto heterocycles through Minisci reaction, such as alkyl, acyl, silyl and alkylthio, etc. Water is eco-friendly and an ideal medium in organic synthesis, which has been applied in Minisci reaction. Recent progress in Minisci reaction in aqueous solution is reviewed herein. Minisci reaction is a convenient method for the functionalization of electron-defficient N-heterocycles. Different substituents could be introduced onto heterocycles through Minisci reaction, such as alkyl, acyl, silyl and alkylthio, boryl, etc. Thus, Minisci reaction is a powerful toolbox for the synthesis of substituted N-heterocylces. Water is eco-friendly and an ideal medium in organic synthesis, which has been applied in Minisci reaction. Although water was used from the discovery of Minisci reaction, Minisci reaction in aqueous solution is still underdeveloped. The recent progress in Minisci reaction in aqueous solution, including alkylation, arylation and acylation, is reviewed according to different radical precursors. Fig. & Tab. | Reference | Related Articles | Metrics Select REVIEWS Photoresponsive Dynamic Supramolecular Assembly and Regulation of Stiff-Stilbenes Qianhong Cao, Yongmei Xiao, Guoxing Liu Chinese Journal of Organic Chemistry 2024, 44 (7): 2124-2135. DOI: 10.6023/cjoc202312026 Accepted: 28 March 2024 Abstract (60) HTML (1) PDF (3050KB)(59) Knowledge map Stimulus-response systems have attracted extensive attention in recent years due to their widespread applications in material science and biological science. Dynamic supramolecular assembly is achieved by introducing stimulus response groups to alter the structure of functional groups and then change supramolecular assembling patterns under the influence of different stimulated factors. As a common molecular photoswitch, stiff-stilbenes have been widely used in controlled catalysis, drug delivery, molecular machinery, tunable phase conversion and so on. Stiff-stilbenes occur Z-E isomerization upon irradiation at diverse light, accompanied by the great alteration of their geometry configuration, and possess good photoisomerization characteristics. Here, some common synthesis methods and photoisomerization mechanism of stiff-stilbene derivatives and their recent research and applications in the fields of photo-switchable ion receptor, light-driven host-guest assembly, photo-responsive hydrogen bond assembly, photoinduced metal bond assembly and photocontrolled hydrophilic and hydrophobic assembly are reviewed. Fig. & Tab. | Reference | Related Articles | Metrics Select REVIEWS Developments in Visible Light Catalyzed Asymmetric Minisci Reactions Wenya Li, Yu Wang, Jiangqi Chen, Dan Shi, Liang Zhang, Xiaochun Yu, Zheng-Jun Wang Chinese Journal of Organic Chemistry 2024, 44 (7): 2110-2123. DOI: 10.6023/cjoc202312016 Accepted: 28 March 2024 Abstract (218) HTML (2) PDF (1041KB)(395) Knowledge map N-Heterocyclic aromatics are among the most prevalent motifs in natural products, pharmaceuticals, and organic materials. Therefore, the selective functionalization of N-heterocyclic aromatics, represented by the Minisci reaction, has always been a hot topic for chemists. Meanwhile, in recent years, photocatalysis has sparked a new research trend as a green, safe, clean, and renewable catalytic method. Although a review has been conducted on photoinduced Minisci reactions in recent years, the exploration of asymmetric Minisci reactions is limited. The research progress on visible-light photocatalytic asymmetric Minisci reactions in recent years from the classification of free radical precursors and different reaction pathways is summarized. Furthermore, prospects for future development are also discussed. Fig. & Tab. | Reference | Related Articles | Metrics Select REVIEWS Advances in the Synthesis of Organogermaniums Based on the Addition Reactions of Alkenes and Alkynes Leiyang Lv, Yani Luo, Zhiping Li Chinese Journal of Organic Chemistry 2024, 44 (7): 2092-2109. DOI: 10.6023/cjoc202401014 Accepted: 10 April 2024 Abstract (142) HTML (1) PDF (949KB)(214) Knowledge map Organogermanium compounds have a wide range of potential applications, especially in the fields of organic synthesis, medicinal chemistry and materials sciences. However, compared with the progress of other elements of the carbon family, the study and development of organogermanium chemistry have long been relatively scattered and sluggish, although it has attracted increasing attention from chemists in recent years. This review aims to introduce the research progress in the synthesis of organogermanium compounds via the addition reactions of alkenes and alkynes. The progress is classified according to the types of addition reactions of germanium with alkenes and alkynes, different reaction systems, reaction mechanisms and synthetic protocols. In addition, the problems encountered during the research process and future development trends are also prospected. 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