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学者姓名:曾程初
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Abstract :
An electrochemical approach for the Minisci-type acylation of quinoxalines with a-keto acids as the acyl radical precursors is reported. With the assistance of TFA as the key additive, acylated quinoxalines were constructed in synthetically useful yields. The distinguishable features of this electrochemical protocol include catalyst-and external oxidant-free conditions, and operational simplicity.
Keyword :
acyl radical acyl radical anodic oxidation anodic oxidation Minisci reaction Minisci reaction & alpha;-keto acids & alpha;-keto acids electrosynthesis electrosynthesis
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GB/T 7714 | Li, Yongmei , Liang, Sen , Wang, Dehui et al. Electrochemical Decarboxylative Minisci-Type Acylation of Quinoxalines under Catalyst- and External-Oxidant-Free Conditions [J]. | SYNTHESIS-STUTTGART , 2023 , 55 (18) : 3026-3032 . |
MLA | Li, Yongmei et al. "Electrochemical Decarboxylative Minisci-Type Acylation of Quinoxalines under Catalyst- and External-Oxidant-Free Conditions" . | SYNTHESIS-STUTTGART 55 . 18 (2023) : 3026-3032 . |
APA | Li, Yongmei , Liang, Sen , Wang, Dehui , Xu, Kun , Zeng, Chengchu . Electrochemical Decarboxylative Minisci-Type Acylation of Quinoxalines under Catalyst- and External-Oxidant-Free Conditions . | SYNTHESIS-STUTTGART , 2023 , 55 (18) , 3026-3032 . |
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Abstract :
The external oxidant-free exploitation of abundant alkane feedstocks as alkyl radical precursors remains a topic of high interest in synthetic communities. Here, we report a Ce-catalyzed electrophotoredox radical addition/cyclization cascade for the incorporation of unactivated alkanes to produce alkylated benzimidazo-fused isoquinolinones and other N-containing polycycles. Compared with previous works employing prefunctionalized alkyl radical precursors, this electrophotocatalytic protocol features high step-economy. The external oxidant-free conditions accompanied by the generation of H2 as the only byproduct further highlight the high redox- and atom-economy of this catalytic protocol. (c) 2022 Elsevier Inc. All rights reserved.
Keyword :
Unactivated alkane Unactivated alkane Cerium catalysis Cerium catalysis Organic electrosynthesis Organic electrosynthesis LMCT LMCT Electrophotocatalysis Electrophotocatalysis
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GB/T 7714 | Tan, Zhoumei , Jiang, Yangye , Xu, Kun et al. Electrophotoredox/cerium-catalyzed unactivated alkanes activation for the sustainable synthesis of alkylated benzimidazo-fused isoquinolinones [J]. | JOURNAL OF CATALYSIS , 2023 , 417 : 473-480 . |
MLA | Tan, Zhoumei et al. "Electrophotoredox/cerium-catalyzed unactivated alkanes activation for the sustainable synthesis of alkylated benzimidazo-fused isoquinolinones" . | JOURNAL OF CATALYSIS 417 (2023) : 473-480 . |
APA | Tan, Zhoumei , Jiang, Yangye , Xu, Kun , Zeng, Chengchu . Electrophotoredox/cerium-catalyzed unactivated alkanes activation for the sustainable synthesis of alkylated benzimidazo-fused isoquinolinones . | JOURNAL OF CATALYSIS , 2023 , 417 , 473-480 . |
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Abstract :
Radical-polar crossover (RPC) reaction bridges the gap between one- and two-electron reactivities, thus providing an ideal solution to overcome the limitations of both radical and polar chemistry. In this manifold, organic electrochemistry provides a uniquely facile strategy to access a diverse array of radical intermediates, thus broadening the chemical space of the RPC concept. This review highlights the synthetic advances in the field of electrochemical RPC reactions since 2020, with an emphasis on the substrate scope, reaction limitation and mechanistic aspect. The related RPC reactions are categorized as net-oxidative, net-reductive, or redox neutral transformations.
Keyword :
alkene functionalization alkene functionalization polar chemistry polar chemistry radical chemistry radical chemistry electrosynthesis electrosynthesis radical-polar crossover radical-polar crossover
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GB/T 7714 | Tan, Zhoumei , Zhang, Haonan , Xu, Kun et al. Electrochemical radical-polar crossover: a radical approach to polar chemistry [J]. | SCIENCE CHINA-CHEMISTRY , 2023 . |
MLA | Tan, Zhoumei et al. "Electrochemical radical-polar crossover: a radical approach to polar chemistry" . | SCIENCE CHINA-CHEMISTRY (2023) . |
APA | Tan, Zhoumei , Zhang, Haonan , Xu, Kun , Zeng, Chengchu . Electrochemical radical-polar crossover: a radical approach to polar chemistry . | SCIENCE CHINA-CHEMISTRY , 2023 . |
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Abstract :
We report a strategic exploitation of trifluoromethyl thianthrenium triflate (TT-CF3+OTf-) as both electromediator and CF3 radical precursors for paired electrolysis. Enabled by this strategy, the three-component trifluoromethylheteroaromatization of alkenes and alkynes was realized. The superiority of TT-CF3+OTf- to other electrophilic CF3 reagents is attributed to the cathodic generation of thianthrene (TT) as a mediator, which shifts the heterogeneous oxidation of interest to a homogeneous one.
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GB/T 7714 | Xiang, Fang , Wang, Dehui , Xu, Kun et al. Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF3 +OTf-) as a Bifunctional Reagent [J]. | ORGANIC LETTERS , 2023 , 26 (1) : 411-415 . |
MLA | Xiang, Fang et al. "Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF3 +OTf-) as a Bifunctional Reagent" . | ORGANIC LETTERS 26 . 1 (2023) : 411-415 . |
APA | Xiang, Fang , Wang, Dehui , Xu, Kun , Zeng, Cheng-Chu . Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF3 +OTf-) as a Bifunctional Reagent . | ORGANIC LETTERS , 2023 , 26 (1) , 411-415 . |
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Abstract :
The electrochemical utilization of electron-deficient methylarenes for radical-radical cross-couplings remains very rare. Enabled by an umpolung strategy, the unprecedented electrochemical cross-coupling of electron-deficient methylarenes with aldehydes was developed. The paired electrolysis simultaneously generated electron-deficient benzylic radicals and ketyl radicals at both electrodes, which then under-went radical recombination, governed by polarity matching and persistent-radical effect (PRE) to afford functionalized alcohols that are not easily accessible by other methods. This protocol features catalyst-and external redox agent-free conditions and a formal 100% atom economy. Mechanistic studies support the radical-radical cross-coupling pathway.
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GB/T 7714 | Lian, Fei , Xu, Kun , Zeng, Chengchu . Electrochemical Umpolung Enabled Radical-Radical Cross-Coupling Between Electron-Deficient Methylarenes and Aldehydes [J]. | CCS CHEMISTRY , 2023 , 5 (9) : 1973-1981 . |
MLA | Lian, Fei et al. "Electrochemical Umpolung Enabled Radical-Radical Cross-Coupling Between Electron-Deficient Methylarenes and Aldehydes" . | CCS CHEMISTRY 5 . 9 (2023) : 1973-1981 . |
APA | Lian, Fei , Xu, Kun , Zeng, Chengchu . Electrochemical Umpolung Enabled Radical-Radical Cross-Coupling Between Electron-Deficient Methylarenes and Aldehydes . | CCS CHEMISTRY , 2023 , 5 (9) , 1973-1981 . |
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Abstract :
The organoselenium-catalyzed amination of alkenes is a promising way to construct functionalized amines. However, the use of chemical oxidants and the unavoidable formation of allylic amine or enamine are the two main limitations of these methodologies. Against this background, we herein report an electro-selenocatalytic regime for the hydroazolylation of alkenes with azoles under external oxidant-free conditions with low catalyst loadings. Moreover, this protocol enables the generation of amines without vinyl substituents.
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GB/T 7714 | Tan, Zhoumei , Xiang, Fang , Xu, Kun et al. Electrochemical Organoselenium-Catalyzed Intermolecular Hydroazolylation of Alkenes with Low Catalyst Loadings [J]. | ORGANIC LETTERS , 2022 , 24 (29) : 5345-5350 . |
MLA | Tan, Zhoumei et al. "Electrochemical Organoselenium-Catalyzed Intermolecular Hydroazolylation of Alkenes with Low Catalyst Loadings" . | ORGANIC LETTERS 24 . 29 (2022) : 5345-5350 . |
APA | Tan, Zhoumei , Xiang, Fang , Xu, Kun , Zeng, Chengchu . Electrochemical Organoselenium-Catalyzed Intermolecular Hydroazolylation of Alkenes with Low Catalyst Loadings . | ORGANIC LETTERS , 2022 , 24 (29) , 5345-5350 . |
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Abstract :
A new oleanane-type triterpene, ardisiapunine A (1), together with eight known compounds were isolated from the roots of Ardisia lindleyana D.Dietr. Their chemical structures were determined by means of spectroscopic methods including HR-ESI-MS and (1 D, 2 D) NMR data. The absolute configuration of compound 1 was established by a single-crystal X-ray diffraction experiment. The new compound is an unusual oleanane-type triterpene bearing an acetal and a C-13-C-18 double bond. The cytotoxicity of all isolated compounds were evaluated using four human cancer cell lines, including A549, HepG2, HeLa and U87. The new compound 1 and compound 2 were weakly active but the known compound 6 exhibited a high cytotoxicity compared to cisplatin.
Keyword :
single-crystal X-ray diffraction single-crystal X-ray diffraction cytotoxic activity cytotoxic activity NMR spectroscopy NMR spectroscopy oleanane-type triterpene oleanane-type triterpene Ardisia lindleyana D Ardisia lindleyana D ardisiapunine A ardisiapunine A Dietr Dietr Primulaceae Primulaceae
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GB/T 7714 | Zhou Tiqiang , Wei Zhenzhen , Fu Qianyu et al. A new oleanane-type triterpene from Ardisia lindleyana D.Dietr and its cytotoxic activity [J]. | NATURAL PRODUCT RESEARCH , 2022 , 37 (15) : 2517-2524 . |
MLA | Zhou Tiqiang et al. "A new oleanane-type triterpene from Ardisia lindleyana D.Dietr and its cytotoxic activity" . | NATURAL PRODUCT RESEARCH 37 . 15 (2022) : 2517-2524 . |
APA | Zhou Tiqiang , Wei Zhenzhen , Fu Qianyu , Qiu Rui , Zhang Guangjie , Li Bin et al. A new oleanane-type triterpene from Ardisia lindleyana D.Dietr and its cytotoxic activity . | NATURAL PRODUCT RESEARCH , 2022 , 37 (15) , 2517-2524 . |
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Abstract :
酰胺化合物中的酰基脱除是有机合成化学的重要研究方向之一.但是,由于酰胺键较为惰性,在温和条件下脱除酰基保护基的报道较少.为了解决上述问题,发展了一种使用氨水脱除酰基保护基的新方法.该方法不但条件温和,而且可以放大规模反应(10 mmol).一系列药物分子或者药物分子衍生物,例如吲哚美辛、N-乙酰基褪黑素及N-乙酰基卡布洛芬中的酰基都可以采用此方法高产率脱除.该方法具有较好的官能团容忍性、操作简便、条件温和、产率高以及所用的试剂廉价易得等优势.因此,该方法有望成为N-酰基脱保护的实用方法之一.
Keyword :
绿色合成 绿色合成 酰胺 酰胺 脱酰基 脱酰基 酰胺基转移 酰胺基转移
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GB/T 7714 | 韩群 , 徐坤 , 田发宁 et al. 一种利用酰胺基转移反应脱除酰基保护基的实用方法(英文) [J]. | 有机化学 , 2022 , 42 (04) : 1123-1128 . |
MLA | 韩群 et al. "一种利用酰胺基转移反应脱除酰基保护基的实用方法(英文)" . | 有机化学 42 . 04 (2022) : 1123-1128 . |
APA | 韩群 , 徐坤 , 田发宁 , 黄胜阳 , 曾程初 . 一种利用酰胺基转移反应脱除酰基保护基的实用方法(英文) . | 有机化学 , 2022 , 42 (04) , 1123-1128 . |
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Abstract :
The N-deacylation of amides under mild conditions is highly desirable in organic synthesis, but it remains challenging due to the chemically robust nature of amide bond. A general solution to the N-deacylation of amides with NH3 center dot H2O under mild and scalable conditions (10 mmol) was developed. A range of drugs and drug derivatives including indomethacin, N-acetvl melatonin and N-acetyl carprofen could be deacylated to release free amines in excellent yields. The good functional group compatibility, combined with operational simplicity, excellent yield and cost effectiveness of all reagents, makes this protocol a prune candidate for N-deacylation of amide.
Keyword :
deacylation deacylation green synthesis green synthesis amide amide transamidation transamidation
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GB/T 7714 | Han Qun , Xu Kun , Tian Faning et al. A Practical Transamidation Strategy for the N-Deacylation of Amides [J]. | CHINESE JOURNAL OF ORGANIC CHEMISTRY , 2022 , 42 (4) : 1123-1128 . |
MLA | Han Qun et al. "A Practical Transamidation Strategy for the N-Deacylation of Amides" . | CHINESE JOURNAL OF ORGANIC CHEMISTRY 42 . 4 (2022) : 1123-1128 . |
APA | Han Qun , Xu Kun , Tian Faning , Huang Shengyang , Zeng Chengchu . A Practical Transamidation Strategy for the N-Deacylation of Amides . | CHINESE JOURNAL OF ORGANIC CHEMISTRY , 2022 , 42 (4) , 1123-1128 . |
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Abstract :
The electrochemical preparation of 2-aminothiazoles has been achieved by the reaction of active methylene ketones with thioureas assisted by ᴅʟ-alanine using NH4I as a redox mediator. The electrochemical protocol proceeds in an undivided cell equipped with graphite plate electrodes under constant current conditions. Various active methylene ketones, including 13-keto ester, 13-keto amide, 13-keto nitrile, 13-keto sulfone and 1,3-diketones, can be converted to the corresponding 2-aminothiazoles. Mechanistically, the in situ generated alpha-iodoketone was proposed to be the key active species.
Keyword :
halide ion halide ion indirect electrolysis indirect electrolysis 2-aminothiazoles 2-aminothiazoles electrosynthesis electrosynthesis
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GB/T 7714 | Yang, Shang-Feng , Li, Pei , Fang, Zi-Lin et al. A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I [J]. | BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY , 2022 , 18 : 1249-1255 . |
MLA | Yang, Shang-Feng et al. "A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I" . | BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 18 (2022) : 1249-1255 . |
APA | Yang, Shang-Feng , Li, Pei , Fang, Zi-Lin , Liang, Sen , Tian, Hong -Yu , Sun, Bao-Guo et al. A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I . | BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY , 2022 , 18 , 1249-1255 . |
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