- Potassium Thioacids Mediated Selective Amide and Peptide Constructions Enabled by Visible Light Photoredox Catalysis
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A remarkable visible-light-promoted photoredox catalytic methodology involved with amines and eco-friendly potassium thioacids for amide formation was uncovered. This approach can mimic the natural coenzyme acetyl-CoA to selectively acylate amines without affecting other functional groups such as alcohols, phenols, esters, among others. The developed strategy may hold great potential for a comprehensive display of biologically interesting peptide synthesis and amino acid modification through a diacyl disulfide intermediate.
- Liu, Hongxin,Zhao, Liyun,Yuan, Yunfei,Xu, Zhifang,Chen, Kai,Qiu, Shengxiang,Tan, Haibo
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Read Online
- Synthesis of N-arylamides by copper-catalyzed amination of aryl halides with nitriles
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A copper-catalyzed amination of aryl halides with nitriles has been developed. The use of nitriles as nitrogen nucleophiles can make the synthesis of N-arylamides more simple than that using amides through in-situ hydrolysis. A variety of N-arylamides and benzoxazole derivatives can be synthesized according to this approach. Copyright
- Xiang, Shi-Kai,Zhang, Dong-Xue,Hu, Hao,Shi, Jiang-Ling,Liao, Li-Guo,Feng, Chun,Wang, Bi-Qin,Zhao, Ke-Qing,Hu, Ping,Yang, Hua,Yu, Wen-Hao
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Read Online
- Highly efficient amide synthesis from alcohols and amines by virtue of a water-soluble gold/DNA catalyst
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Gold takes to water: The synthesis of amides directly from alcohols and amines was realized by using a water-soluble Au/DNA nanohybrid as the catalyst. The interactions between the gold nanoparticles, DNA, and water lead to high catalytic efficiency under mild reaction conditions. The wide substrate scope includes less-basic aromatic amines, and this catalyst is recyclable.
- Wang, Ye,Zhu, Dapeng,Tang, Lin,Wang, Sujing,Wang, Zhiyong
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Read Online
- Aerobic oxidative transformation of primary alcohols and amines to amides promoted by a hydroxyapatite-supported gold catalyst in water
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In the presence of an easily prepared hydroxyapatite-supported gold catalyst, namely Au/HAP, various kinds of structurally diverse primary alcohols including benzylic and aliphatic ones, and amines involving aromatic and secondary ones could be converted into the corresponding amides in water with up to 99% yield. Meanwhile, on the basis of experimental observations and literatures, a plausible reaction pathway was described to elucidate the reaction mechanism.
- Wang, Wentao,Cong, Yu,Zhang, Leilei,Huang, Yanqiang,Wang, Xiaodong,Zhang, Tao
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Read Online
- An Iron-Catalyzed Direct Approach to Amides from Benzyl Azides via C-C Bond Cleavage
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A novel iron-catalyzed transformation of benzyl azides to give the corresponding amides via C-C bond cleavage under mild reaction conditions is developed. This method provides a new synthetic tool for the construction of amides and the opportunity to accomplish C-C functionalization under mild conditions.
- Ou, Yang,Qin, Chong,Song, Song,Jiao, Ning
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Read Online
- An improved protocol for synthesis of N-arylamides and benzoxazoles by the copper-catalyzed reaction of aryl halides with nitriles
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An improved protocol for the synthesis of N-arylamides and benzoxazoles by the copper-catalyzed reaction of aryl halides with nitriles has been developed. Use of acetaldoxime as the hydrolysis reagent instead of H2O facilitates the operation of the reaction. The significantly decreased amount of nitriles, along with use of weak base K2CO3 instead of strong base KOH, makes this transformation atom-efficient and environmentally benign. A variety of N-arylamides and benzoxazole derivatives can be synthesized according to this approach.
- Zhang, Dong-Xue,Xiang, Shi-Kai,Hu, Hao,Tan, Wen,Feng, Chun,Wang, Bi-Qin,Zhao, Ke-Qing,Hu, Ping,Yang, Hua
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Read Online
- Direct hydrogenation of nitroaromatics and one-pot amidation with carboxylic acids over platinum nanowires
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A novel ultrathin platinum nanowire with uniform length and a diameter of 1.5 nm was synthesized by acidic etching of FePt nanowire in methanol. This nanowire was characterized by high-resolution transmission electron microscopy (HRTEM). X-ray diffraction (XRD) data indicated that the main plane is (111). The ability of this nanowire to catalyze the heterogeneous hydrogenation of nitroaromatics to give the corresponding amines has been investigated. The catalyst showed satisfactory activity in various solvents under mild conditions and showed excellent stability. The catalytic performance was also evaluated in the one-pot reduction of nitroaromatics and amidation with carboxylic acids under a hydrogen atmosphere at 100°C. These methods for the hydrogenation of nitroaromatics and the direct amidation of nitroaromatics with carboxylic acids are simple, economical, and environmentally benign, and have practical advantages for the synthesis of amines and amides without the production of toxic byproducts.
- Li, Min,Hu, Lei,Cao, Xueqin,Hong, Haiyan,Lu, Jianmei,Gu, Hongwei
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Read Online
- Direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions
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The direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions has been developed. The reported protocol is practical and represents an efficient method to produce functionalized amides in moderate to good yields.
- Xiong, Biquan,Wang, Gang,Xiong, Tao,Wan, Liming,Zhou, Congshan,Liu, Yu,Zhang, Panliang,Yang, Changan,Tang, Kewen
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Read Online
- Iron-Catalyzed Photoredox Functionalization of Methane and Heavier Gaseous Alkanes: Scope, Kinetics, and Computational Studies
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Herein, we report the development of the photocatalytic C-H functionalization of methane, ethane, and heavier gaseous alkanes with good yields and selectivity, broad scope (57 examples), mild conditions, and low cost. Kinetics and density functional theor
- Zhang, Qingqing,Liu, Shuyang,Lei, Jinglan,Zhang, Yongqiang,Meng, Changgong,Duan, Chunying,Jin, Yunhe
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supporting information
p. 1901 - 1906
(2022/03/27)
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- Visible-light induced one-pot hydrogenation and amidation of nitroaromatics with carboxylic acids over 2D MXene-derived Pt/N-TiO2/Ti3C2
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Pt nanoparticles supported on N doped titanium dioxide/titanium carbide (MXene) heterojunctions were employed as photocatalysts for the tandem reactions between aromatic nitro compounds and carboxylic acids to produce amide products. The 3%Pt/N-TiO2/Ti3C2 heterojunction was prepared by in situ grew TiO2 on Ti3C2 nanosheets and then N doped TiO2 with melamine, Pt nanoparticles with 3.3 nm mean diameter well dispersed on N-TiO2/Ti3C2. 3%Pt/N-TiO2/Ti3C2 had excellent amidation activity and chemoselectivity under visible-light irradiation. The elevated catalytic performance of 3%Pt/N-TiO2/Ti3C2 was owing to the improvement in photogenerated electron and hole separation efficiency through charge short-range directional transmission caused by the intimate contact between the TiO2 and the conductive Ti3C2. This direct hydrogenation along with amidation between nitroaromatics and carboxylic acids own actual merits in the amides produce with no harmful byproducts. In situ DRIFTS spectra verified that the amidation activation with visible light irradiation at 25 °C was much faster than heating.
- Jiang, Heyan,Hu, Zujie,Gan, Chuan,Sun, Bin,Kong, Shuzhen,Bian, Fengxia
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- Asymmetric Markovnikov Hydroaminocarbonylation of Alkenes Enabled by Palladium-Monodentate Phosphoramidite Catalysis
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A palladium-catalyzed asymmetric Markovnikov hydroaminocarbonylation of alkenes with anilines has been developed for the atom-economical synthesis of 2-substituted propanamides bearing an α-stereocenter. A novel phosphoramidite ligand L16 was discovered which exhibited very high reactivity and selectivity in the reaction. This asymmetric Markovnikov hydroaminocarbonylation employs readily available starting materials and tolerates a wide range of functional groups, thus providing a facile and straightforward method for the regio- and enantioselective synthesis of 2-substituted propanamides under ambient conditions. Mechanistic studies revealed that the reaction proceeds through a palladium hydride pathway.
- Yao, Ya-Hong,Yang, Hui-Yi,Chen, Ming,Wu, Fei,Xu, Xing-Xing,Guan, Zheng-Hui
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supporting information
p. 85 - 91
(2021/01/12)
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- Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization-Hydroboration of Unactivated Alkenes
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A tungsten-catalyzed hydroboration of unactivated alkenes at distal C(sp3)-H bonds aided by native directing groups is described herein. The method is characterized by its simplicity, exquisite regio- and chemoselectivity, and wide substrate scope, offering a complementary site-selectivity pattern to other metal-catalyzed borylation reactions and chain-walking protocols.
- Cooper, Phillippa,Engle, Keary M.,Jankins, Tanner C.,Martin, Ruben,Martin-Montero, Raul
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p. 14981 - 14986
(2021/09/29)
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- Efficient nitriding reagent and application thereof
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The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.
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Paragraph 0176-0178
(2021/03/31)
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- Method for promoting acylation of amine or alcohol by carbon dioxide
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The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.
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Paragraph 0033-0034
(2021/05/29)
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- Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant
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An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.
- Yi, Xuewen,Yi, Xuewen,Lei, Siyu,Liu, Wangsheng,Che, Fengrui,Yu, Chunzheng,Liu, Xuesong,Wang, Zonghua,Zhou, Xin,Zhang, Yuexia
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supporting information
p. 4583 - 4587
(2020/05/05)
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- First Structure-Activity Relationship Study of Potent BLT2 Agonists as Potential Wound-Healing Promoters
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The first potent leukotriene B4 (LTB4) receptor type 2 (BLT2) agonists, endogenous 12(S)-hydroxyheptadeca-5Z,8E,10E-trienoic acid (12-HHT), and synthetic CAY10583 (CAY) have been recently described to accelerate wound healing by enhanced keratinocyte migration and indirect stimulation of fibroblast activity in diabetic rats. CAY represents a very valuable starting point for the development of novel wound-healing promoters. In this work, the first structure-activity relationship study for CAY scaffold-based BLT2 agonists is presented. The newly prepared derivatives showed promising in vitro wound-healing activity.
- Hernandez-Olmos, Victor,Heering, Jan,Planz, Viktoria,Liu, Ting,Kaps, Alexander,Rajkumar, Rinusha,Gramzow, Matthias,Kaiser, Astrid,Schubert-Zsilavecz, Manfred,Parnham, Michael J.,Windbergs, Maike,Steinhilber, Dieter,Proschak, Ewgenij
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supporting information
p. 11548 - 11572
(2020/11/26)
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- Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles
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The Schmidt reaction has been an efficient and widely used synthetic approach to amides and nitriles since its discovery in 1923. However, its application often entails the use of volatile, potentially explosive, and highly toxic azide reagents. Here, we report a sequence whereby triflic anhydride and formic and acetic acids activate the bulk chemical nitromethane to serve as a nitrogen donor in place of azides in Schmidt-like reactions. This protocol further expands the substrate scope to alkynes and simple alkyl benzenes for the preparation of amides and nitriles.
- Jiao, Ning,Liu, Jianzhong,Qiu, Xu,Song, Song,Wei, Jialiang,Wen, Xiaojin,Zhang, Cheng,Zhang, Ziyao
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supporting information
p. 281 - 285
(2020/01/28)
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- Iridium-Catalyzed Distal Hydroboration of Aliphatic Internal Alkenes
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The regioselective hydroboration of aliphatic internal alkenes remains a great challenge. Reported herein is an iridium-catalyzed hydroboration of aliphatic internal alkenes, providing distal-borylated products in good to excellent yields with high regioselectivity (up to 99:1). We also demonstrate that the C?B bond of the distal-borylated product can be readily converted into other functional groups. DFT calculations indicate that the reaction proceeds through an unexpected IrIII/IrV cycle.
- Wang, Guangzhu,Liang, Xinyi,Chen, Lili,Gao, Qian,Wang, Jian-Guo,Zhang, Panke,Peng, Qian,Xu, Senmiao
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p. 8187 - 8191
(2019/05/27)
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- Iodine-mediated aryl transfer reaction from arylhydrazine hydrochlorides to nitriles
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An iodine-promoted, metal-, base-, and solvent-free cross-coupling reaction was developed for the synthesis of various useful secondary amides via an aryl N-addition reaction of aryl groups to cyano groups. This aryl transfer reaction proceeds with arylhydrazine hydrochlorides serving as the aryl donors. A labelling experiment shows that the N atom in the product comes from the cyano group of the nitriles, which are low in cost. A plausible radical-driven mechanism is also proposed.
- Zhang, Zhiguo,Li, Xiang,Li, Yinghua,Guo, Yan,Zhao, Xunan,Yan, Yan,Sun, Kai,Zhang, Guisheng
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supporting information
p. 3628 - 3635
(2019/05/29)
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- Synthesis of Secondary Amides from Thiocarbamates
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The synthesis of secondary amides from readily accessible and bench-stable substituted S-phenyl thiocarbamates and Grignard reactants is reported. Oxidative workup allows recycling of the thiolate leaving group as diphenyl disulfide. Diphenyl disulfide can be transformed into S-phenyl benzenethiosulfonate, a reactant required for thiocarbamate synthesis. This amide synthesis is suitable for the preparation of challenging amides that are not or hardly accessible via classical approaches.
- Mampuys, Pieter,Ruijter, Eelco,Orru, Romano V. A.,Maes, Bert U. W.
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p. 4235 - 4239
(2018/07/29)
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- NOVEL COMPOUND HAVING BLT INHIBITORY ACTIVITY AND COMPOSITION, FOR PREVENTING OR TREATING INFLAMMATORY DISEASES, COMPRISING SAME AS ACTIVE INGREDIENT
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The present invention relates to a novel compound showing leukotriene B4 receptor 2 (BLT2) inhibitory activity and a pharmaceutical composition, for preventing or treating inflammatory diseases, comprising same as an active ingredient. The inventors identified a novel compound containing BTL2 inhibitory activity, and experimentally confirmed that the present novel compound had an excellent effect on the enhancement of the cancer cell death, on the inhibition of the metastasis and chemotactic mobility, and on the anti-asthma activity. Therefore, the present novel compound can be used as a very effective pharmaceutical component for treating the inflammatory-related diseases.
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Paragraph 0043; 0114
(2018/06/07)
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- A to aryl diazonium tetrafluoroborate salts with a nitrile preparation machine acid radical amine compounds (by machine translation)
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The invention provides a high-efficiency, high-selective synthesis of different substituted functional group containing organic amide compound, it adopts the cuprous iodide as a catalyst, in order to aryl diazonium tetrafluoroborate salts compounds and organic nitrile compound as the reaction substrate, the reaction system by adding the organic solvent, water and alkali. The advantage of this method: cheap and easily obtained catalyst; the substrate has a high applicability; mild reaction conditions, safe and reliable; the resulting target product selectivity is close to 100%, yield is as high as 90% or more. The method solves the traditional synthetic organic amide compound of rigorous reaction conditions, the reaction selectivity is poor, the experimental procedure is complicated, the productivity is low and needs to be used for the environment of a harmful reagent and the like, it has good industrial application prospect. The invention also provides a corresponding different substituted functional group containing organic amide compound. (by machine translation)
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Paragraph 0028
(2018/06/04)
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- N - substituted benzyl amino phosphine pliers link ruthenium double phosphine compound and its preparation method and application
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The invention relates to an N-substituted benzylaminophosphonic pincer-type cyclo-ruthenium diphosphonic compound, and a preparation method and an application for the N-substituted benzylaminophosphonic pincer-type cyclo-ruthenium diphosphonic compound. The preparation method comprises the following steps of adding amine phosphine, substituted benzyl alcohol, diphosphine ligand, RuC12(PPh3)3 and alkali into organic solvent; heating the mixture under the protection of N2 gas; filtering and recrystallizing the mixture so as to obtain the N-substituted benzylaminophosphonic pincer-type cyclo-ruthenium diphosphonic compound after the reaction is completed, wherein the process of synthesizing the N-substituted benzylaminophosphonic pincer-type cyclo-ruthenium diphosphonic compound is eliminated, so that the reaction operation is simple, and the preparation is easy. According to the preparation method, the N-substituted benzylaminophosphonic pincer-type cyclo-ruthenium diphosphonic compound is taken as a metal catalyst for catalytically synthesizing and preparing amide compounds. The preparation method has the advantages of low price and wide range of reaction substrates, mild condition, high efficiency and practicability, and has important application values.
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Paragraph 0072; 0073
(2017/10/07)
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- Hypervalent Iodine-Mediated Oxidative Rearrangement of N-H Ketimines: An Umpolung Approach to Amides
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An umpolung approach to amides via hypervalent iodine-mediated oxidative rearrangement of N-H ketimines under mild reaction conditions is described. This strategy provides target amides with excellent selectivity in good yields. In addition, preliminary m
- Zhao, Zhenguang,Peng, Zhiyuan,Zhao, Yongli,Liu, Hao,Li, Chongnan,Zhao, Junfeng
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p. 11848 - 11853
(2017/11/28)
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- Hypervalent Iodine(III)-Promoted Phenyl Transfer Reaction from Phenyl Hydrazides to Nitriles
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A useful transformation of nitriles to N-phenyl amides has been achieved through a novel intermolecular phenyl transfer reaction from phenyl hydrazides and N-addition to nitriles in the presence of PIFA under mild and solvent-free conditions. This cross-coupling reaction includes the oxidative cleavage of sp2 C-N bonds of phenyl hydrazides to form a phenyl radical and the subsequent N-addition to cyanos to form new sp2 C-N bonds and provides efficient access to various N-phenyl amides in moderate to good yields under mild reaction conditions.
- Yan, Yan,Zhang, Zhiguo,Wan, Yameng,Zhang, Guisheng,Ma, Nana,Liu, Qingfeng
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supporting information
p. 7957 - 7963
(2017/08/14)
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- Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp3)-H Bonds
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An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp3)-H bonds through radical 1,5-hydrogen abstraction. The γ-bromoamides formed are subsequently converted to γ-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp3-hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of γ-lactones into complex carbon frameworks.
- Richers, Johannes,Heilmann, Michael,Drees, Markus,Tiefenbacher, Konrad
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supporting information
p. 6472 - 6475
(2016/12/23)
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- Amidation of Carboxylic Acids with Amines by Nb2O5 as a Reusable Lewis Acid Catalyst
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Among 28 types of heterogeneous and homogenous catalysts tested, Nb2O5 shows the highest yield for direct amidation of n-dodecanoic acid with a less reactive amine (aniline). The catalytic amidation by Nb2O5 is applicable to a wide range of carboxylic acids and amines with various functional groups, and the catalyst is reusable. A comparison of the results of the catalytic study and an infrared study of the acetic acid adsorbed on the catalyst suggests that activation of the carbonyl group of the carboxylic acid by Lewis acid sites on Nb2O5 is responsible for the high activity of the Nb2O5 catalyst. Kinetic studies show that Lewis acid sites on Nb2O5 are more water-tolerant than conventional Lewis acidic oxides (Al2O3, TiO2). In comparison with the state-of-the-art homogeneous Lewis acid catalyst for amidation (ZrCl4), Nb2O5 undergoes fewer negative effects from basic additives in the solution, which indicates that Nb2O5 is a more base-tolerant Lewis acid catalyst than the homogeneous Lewis acid catalyst.
- Ali,Siddiki,Onodera, Wataru,Kon, Kenichi,Shimizu, Ken-Ichi
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p. 3555 - 3561
(2015/11/10)
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- Mild and Efficient Cobalt-Catalyzed Cross-Coupling of Aliphatic Amides and Aryl Iodides in Water
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A convenient protocol for the C-N cross-coupling of aliphatic amides and iodobenzene is demonstrated using a simple and inexpensive Co(C2O4)·2H2O/N,N′-dimethylethylenediamine (DMEDA) catalytic system in water. Good yields of N-arylated products were isolated (up to 85%) and the protocol has been successfully applied to the synthesis of the anticancer drug, flutamide.
- Tan, Bryan Yong-Hao,Teo, Yong-Chua
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supporting information
p. 1697 - 1701
(2015/07/20)
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- Hydromethylation of Unactivated Olefins
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A solution to the classic unsolved problem of olefin hydromethylation is presented. This highly chemoselective method can tolerate labile and reactive chemical functionalities and uses a simple set of reagents. An array of olefins, including mono-, di-, and trisubstituted olefins, are all smoothly hydromethylated. This mild protocol can be used to simplify the synthesis of a specific target or to directly "edit" complex natural products and other advanced materials. The method is also amenable to the simple installation of radioactive and stable labeled methyl groups.
- Dao, Hai T.,Li, Chao,Michaudel, Quentin,Maxwell, Brad D.,Baran, Phil S.
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supporting information
p. 8046 - 8049
(2015/07/15)
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- Copper-Catalyzed Aerobic Oxidative C-C Bond Cleavage of Unstrained Ketones with Air and Amines
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A unique copper-catalyzed aerobic oxidative C-C bond cleavage of simple unstrained ketones with air and amines has been developed. In this chemistry, amides and oxo amides are easily synthesized through the selective C-C bond cleavage of simple ketones or unstrained cycloketones. The broad substrate scopes and use of an inexpensive copper catalyst and green molecular oxygen as an oxidant as well as an O-source make this protocol very attractive for potential synthetic applications. The control experiments reveal that the present copper-catalyzed oxidative C-C bond cleavage of simple ketones proceeds in a novel catalytic pathway rather than through the cleavage of a dioxetane intermediate. (Chemical Equation Presented).
- Zhou, Wang,Fan, Wenyou,Jiang, Qijian,Liang, Yu-Feng,Jiao, Ning
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supporting information
p. 2542 - 2545
(2015/05/27)
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- Aerobic oxidative coupling of alcohols and amines over Au-Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines
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A facile switch of the reaction pathways of aerobic oxidative coupling of alcohols and amines from amidation to imination was realized for the first time by tuning the Au/Pd ratios in ion-exchange resin supported Au-Pd alloy catalysts (Au-Pd/resin). Amides were obtained with high yields on Au6Pd/resin while imines were obtained over AuPd4/resin. Various alcohols and amines underwent oxidative coupling smoothly in water to afford the desired products with good to excellent yields. Further investigation on the reaction mechanism suggested the synergistic effect between Au and Pd determined the adsorption strength of the aldehyde intermediate, which in turn dictated the reaction pathways. That is, on Au-rich alloys (e.g., Au6Pd) absorbed aldehyde species was formed, followed by further oxidation to yield amides, while on Pd-rich alloys (e.g., AuPd4), free aldehyde was generated, which then underwent condensation with amines to produce imines. The discovery might provide avenues to develop new efficient catalysts for the green synthesis of special chemicals.
- Zhang, Leilei,Wang, Wentao,Wang, Aiqin,Cui, Yitao,Yang, Xiaofeng,Huang, Yanqiang,Liu, Xiaoyan,Liu, Wengang,Son, Jin-Young,Oji, Hiroshi,Zhang, Tao
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supporting information
p. 2680 - 2684
(2013/10/08)
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- Copper(II)-catalyzed three-component cascade annulation of diaryliodoniums, nitriles, and alkynes: A regioselective synthesis of multiply substituted quinolines
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Three become one: Multiply substituted quinolines were synthesized from diaryliodoniums, alkynes, and nitriles by a CuII-catalyzed method. This cascade annulation is highly regioselective, step-economic, flexible with regard to the functional groups, and could potentially be applied to the synthesis of complex molecules. Copyright
- Wang, Yong,Chen, Chao,Peng, Jing,Li, Ming
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supporting information
p. 5323 - 5327
(2013/06/05)
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- Dynamics of catalytic resolution of 2-lithio-N-Boc-piperidine by ligand exchange
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The dynamics of the racemization and catalytic and stoichiometric dynamic resolution of 2-lithio-N-Boc-piperidine (7) have been investigated. The kinetic order in tetramethylethylenediamine (TMEDA) for both racemization and resolution of the title compound and the kinetic orders in two resolving ligands have been determined. The catalytic dynamic resolution is second order in TMEDA and 0.5 and 0.265 order in chiral ligands 8 and 10, respectively. The X-ray crystal structure of ligand 10 shows it to be an octamer. Dynamic NMR studies of the resolution process were carried out. Some of the requirements for a successful catalytic dynamic resolution by ligand exchange have been identified.
- Beng, Timothy K.,Tyree, William S.,Parker, Trent,Su, Chicheung,Williard, Paul G.,Gawley, Robert E.
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supporting information
p. 16845 - 16855
(2013/01/15)
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- Controlling hazardous chemicals in microreactors: Synthesis with iodine azide
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Aromatic aldehydes have been converted into the corresponding carbamoyl azides using iodine azide. These reactions have been performed safely under continuous flow reaction conditions in microreactors.
- Brandt, Johan C.,Wirth, Thomas
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experimental part
(2010/04/22)
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- PROCESS FOR PREPARING AMIDES FROM ALCOHOLS AND AMINES
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The present invention provides a process for preparing amides, by reacting a primary amine and a primary alcohol in the presence of a Ruthenium catalyst, to generate the amide and molecular hydrogen. According to the process of the invention, primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. This reaction is catalyzed by a Ruthenium complex, which is preferably based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3. Use of diamines in the reaction leads to bis-amides, whereas with a mixed primary/secondary amine substrate, chemoselective acylation of the primary amine group occurs.
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Page/Page column 7-8; 11
(2009/05/28)
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- Zinc oxide (ZnO) as a new, highly efficient, and reusable catalyst for acylation of alcohols, phenols and amines under solvent free conditions
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Zinc oxide (ZnO) is a highly efficient catalyst for the acylation of a variety of alcohols, phenols and amines with acid chlorides or acid anhydrides under solvent free conditions. Primary, secondary, tertiary, allylic and benzylic alcohols, diols and phenols with electron donating or withdrawing substituents can be easily acylated in good to excellent yield.
- Hosseini Sarvari, Mona,Sharghi, Hashem
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p. 10903 - 10907
(2007/10/03)
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- Uncatalyzed conversion of linear α-nitro ketones into amides by reaction with primary amines under solventless conditions
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The reaction of linear α-nitro ketones with primary amines allows the formation of amides through the cleavage of the carbon-carbon bond between the carbonyl group and the carbon-nitro group moiety, promoted by the nucleophilic effect of the amine. The re
- Ballini, Roberto,Bosica, Giovanna,Fiorini, Dennis
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p. 1143 - 1145
(2007/10/03)
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- Rhodium-catalyzed Beckmann rearrangement
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equation presented Beckmann rearrangement of oxime is catalyzed by [RhCl(cod)]2, trifluoromethanesulfonic acid, and tris(p-tolyl)phosphine in refluxing dichloroethane, giving the corresponding amide in good yield. Product/acid ratios of 10:20 can be attained in the reaction of benzophenone oximes.
- Arisawa, Mieko,Yamaguchi, Masahiko
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p. 311 - 312
(2007/10/03)
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- Unexpected formation of substituted anilides via reactions of trifluoroacetanilides with lithium reagents
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Reactions of trifluoroacetanilides with various organolithium reagents give the corresponding substituted anilides in good yields.
- Smith, Keith,El-Hiti, Gamal A.,Hamilton, Anna
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p. 4041 - 4042
(2007/10/03)
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- N-Cyanazoles in Synthesis of Amides of Carboxylic Acids
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The reaction of carboxylic acids with 1-cyanimidazole, 1-cyanobenzimidazole, and 1-cyano-1,2,4-triazole leads to the formation of 1-acylazoles used in situ in synthesis of anilides of the corresponding carboxylic acids.
- Purygin,Pan'kov
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p. 871 - 873
(2007/10/03)
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- Directed Ortho-Lithiation of Phenylcarbamic Acid 1,1-Dimethylethyl Ester (N-Boc-aniline). Revision and Improvements
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Evaluation of the results of a study, undertaken to examine the influence of the main reaction parameters (lithiation temperature, concentration, lithiating agent, and solvent) on the course of the title reaction, subsequently led to the development of an improved and more generally-applicable lithiation procedure.Hitherto unpublished stability data for solutions of t-BuLi and n-BuLi/TMEDA in diethyl ether and THF are reported for various temperatures.
- Stanetty, Peter,Koller, Herbert,Mihovilovic, Marko
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p. 6833 - 6837
(2007/10/02)
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- Clay Catalysed Facile Beckmann Rearrangement of Ketoximes
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Beckmann rearrangement is reported using montmorilonite KSF, an acidic clay.
- Meshram, H.M.
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p. 3253 - 3258
(2007/10/02)
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- Cp2TiCl2-CATALYZED REACTION OF GRIGNARD REAGENTS WITH ISOCYANATES, FORMATION OF CARBOXAMIDE WITH REARRANGED CARBONSKELETON
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Isocyanates react with isopropyl or sec-butylmagnesium bromide in the presence of a small amount of Cp2TiCl2 to afford amides with normal alkyl group.A possibl mechanism for this reaction is proposed.
- Zhang, Yongmin,Jiang, Jinlong,Chen, Yongqian
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p. 3815 - 3816
(2007/10/02)
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- SYNTHESIS AND PROPERTIES OF THIOACYLANILIDE FLOTATION REAGENT.
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Investigations have shown that a compound with a thioamide group from the thioacylanilide class, of the following structure, is an effective flotation reagent. With the aim of using this reagent in ore flotation, the authors studied the conditions of its synthesis and some of its physicochemical properties. The method based on the reaction of acylanilides with tetraphosphorus decasulfide is the most suitable for industrial operation. Experimental data show that by the use of a small excess of acylanilide it is possible to obtain a high yield of a product having the required viscosity and to dispense with solvents. The physicochemical properties of the reagent have been investigated.
- Ryaboi,Poroshina,Starovoitov,Gnatyuk,Malii,Polyanskii
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p. 1082 - 1084
(2007/10/02)
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- C-C VERKNUEPFUNG VON ALKENEN MIT ISOCYANATEN AM NICKEL(0)
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Isocyanates react with alkenes, e.g. ethylene and propene, in a C-C bond forming reaction on ligand-nickel(0) systems to yield azanickelacyclopentanones.These metallacycles have been characterized spectroscopically, and their reaction behaviour is discussed.The regioisomeric distribution of the C-C coupling reaction is reported for the reaction with propene.The azanickelacyclopentanones obtained from isocyanates and alkenes react further with ethylene to give ring expansion, whereopen β-elimination to unsaturated amides follows.
- Hoberg, Heinz,Suemmermann, Klaus,Milchereit, Armin
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p. 237 - 248
(2007/10/02)
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