- Synthesis of 1,4-Diazepanes and Benzo[ b][1,4]diazepines by a Domino Process Involving the in Situ Generation of an Aza-Nazarov Reagent
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A step-and atom-economical protocol allowing the synthesis of 1,4-diazepanes and also tetrahydro-and decahydro-1,5-benzodiazepines is described. The method proceeds from very simple starting materials such as 1,2-diamines and alkyl 3-oxohex-5-enoates and can be performed under solvent-free conditions in many instances. The key event of this process was the generation in situ of an aza-Nazarov reagent and its subsequent intramolecular aza-Michael cyclization. An intermolecular version of the reaction was also established and applied to the synthesis of the first example of the pyrrolo[1,2-A][1,5]diazonine framework.
- Maiti, Swarupananda,Leonardi, Marco,Cores, ángel,Tenti, Giammarco,Ramos, M. Teresa,Villacampa, Mercedes,Menéndez, J. Carlos
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- Direct N-alkylation of isatin by halomethyl ketones
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Solid-phase syntheses are reported for 1-(2-oxoalkyl)indoline-2,3-diones. 2005 Springer Science+Business Media, Inc.
- Rekhter
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Read Online
- Direct Synthesis of 4-Aryl-1,2,3-triazoles via I2-Promoted Cyclization under Metal- And Azide-Free Conditions
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We herein report an iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved
- Geng, Xiao,Huang, Chun,Wang, Li-Sheng,Wu, An-Xin,Wu, Yan-Dong,Yu, Xiao-Xiao,Zhao, Peng,Zhou, You
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p. 13664 - 13672
(2021/10/01)
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- One pot synthesis of α-N-heteroaryl ketone derivatives from aryl ketones using aqueous NaICl2
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A simple and efficient method for the synthesis of α-heteroaryl ketones from aryl ketones and amine using aqueous sodium dichloroiodate is established. This method is mild, operationally simple, has a short reaction time, and easy workup procedure to afford the corresponding α-N-heteroaryl ketone derivatives in moderate to good yield.
- Ghodse, Shrikant M.,Hatvate, Navnath T.,Telvekar, Vikas N.
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- Construction and regulation of imidazo[1,5-a]pyridines with AIE characteristics via iodine mediated Csp2?H or Csp?H amination
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The widespread applications of aggregation-induced emission luminogens (AIEgens) inspire the creation of AIEgens with novel structures and functionalities. In this work, we focused on the direct and efficient synthesis of a new type of AIEgens, imidazo[1,5-a]pyridicne derivatives, via iodine mediated cascade oxidative Csp2–H or Csp–H amination route from phenylacetylene or styrenes under mild conditions. The resulted compounds showed excellent AIE characteristics with tunable maximum emissions, attractive bioimaging performance, and potential anti-inflammatory activity, which exert broad application prospects in material, biology, medicine, and other relevant areas.
- Zhang, Jun,She, Mengyao,Liu, Lang,Liu, Mengdi,Wang, Zhaohui,Liu, Hua,Sun, Wei,Liu, Xiaogang,Liu, Ping,Zhang, Shengyong,Li, Jianli
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supporting information
p. 3083 - 3086
(2021/06/28)
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- A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions
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A practical synthesis of α-bromo/iodo/chloroketones from olefins under visible-light irradiation conditions has been developed. In the presence of PhI(OAc)2 as promoter and under ambient conditions, the reactions of styrenes and triiodomethane undergo the transformation smoothly to deliver the corresponding α-iodoketones without additional photocatalyst in good yields under sunlight irradiation. Meanwhile, the reactions of styrenes with tribromomethane and trichloromethane generate the desired α-bromoketones and α-chloroketones in high yields by using Ru(bpy)3Cl2 as a photocatalyst under blue LED (450–455 nm) irradiation.
- Wang, Zhihui,Wang, Lei,Wang, Zhiming,Li, Pinhua,Zhang, Yicheng
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supporting information
p. 429 - 432
(2020/02/29)
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- Methyl Radical Initiated Kharasch and Related Reactions
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An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).
- Tappin, Nicholas D. C.,Renaud, Philippe
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supporting information
p. 275 - 282
(2020/12/07)
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- Direct Trifluoromethoxylation without OCF3-Carrier through In Situ Generation of Fluorophosgene
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Owing to the high interest in the OCF3 group for pharmaceutical and agrochemical applications, trifluoromethoxylation received great attention in the last years with several new methods for this approach towards OCF3-comprising compounds. Yet, it most often requires the beforehand preparation of specific F3CO? transfer reagents, which can be toxic, expensive, unstable, and/or generate undesired side-products upon consumption. To circumvent this, the in-situ generation of gaseous fluorophosgene from triphosgene, its conversion by fluoride into the OCF3 anion, and the direct use of the latter in nucleophilic substitutions is an appealing strategy, which, although recently approached, has not been fully exploited. We disclose herein our efforts towards this aim.
- Donnard, Morgan,Guérin, Thomas,Hanquet, Gilles,Leroux, Frédéric R.,Panossian, Armen,Saiter, Jérémy
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supporting information
p. 3139 - 3147
(2021/06/26)
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- V2O5@TiO2 Catalyzed Green and Selective Oxidation of Alcohols, Alkylbenzenes and Styrenes to Carbonyls
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The versatile application of different functional groups such as alcohols (1° and 2°), alkyl arenes, and (aryl)olefins to construct carbon-oxygen bond via oxidation is an area of intense research. Here, we report a reusable heterogeneous V2O5@TiO2 catalyzed selective oxidation of various functionalities utilizing different mild and eco-compatible oxidants under greener reaction conditions. The method was successfully applied for the alcohol oxidation, oxidative scission of styrenes, and benzylic C?H oxidation to their corresponding aldehydes and ketones. The utilization of mild and eco-friendly oxidizing reagents such as K2S2O8, H2O2 (30 % aq.), TBHP (70 % aq.), broad substrate scope, gram-scale synthesis, and catalyst recyclability are notable features of the developed protocol.
- Upadhyay, Rahul,Kumar, Shashi,Maurya, Sushil K.
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p. 3594 - 3600
(2021/07/02)
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- Multicomponent Synthesis of Imidazo[1,2- a]pyridines: Aerobic Oxidative Formation of C-N and C-S Bonds by Flavin-Iodine-Coupled Organocatalysis
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Herein, we report an aerobic oxidative C-N bond-forming process that enables the facile synthesis of imidazo[1,2-a]pyridines and takes advantage of a coupled organocatalytic system that uses flavin and iodine. Furthermore, the dual catalytic system can be applied to the one-pot, three-step synthesis of 3-thioimidazo[1,2-a]pyridines from aminopyridines, ketones, and thiols.
- Okai, Hayaki,Tanimoto, Kazumasa,Ohkado, Ryoma,Iida, Hiroki
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p. 8002 - 8006
(2020/11/02)
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- Au(I)-Catalyzed Hydration of 1-Iodoalkynes Leading to α-Iodoketones
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A catalytic protocol for the Au(I)-catalyzed hydration of 1-iodoalkynes is disclosed. The use of Au(I)–NHC catalyst enabled the straightforward synthesis of a variety of α-iodomethyl ketones in good to excellent yields. The utility of this simple method is further highlighted by showcasing iodination/hydration and hydration/oxidation sequential protocols leading to the construction of molecular complexity.
- Cazin, Catherine S. J.,Gómez-Herrera, Alberto,Hashim, Ishfaq Ibni,Nahra, Fady,Porré, Marre
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p. 6790 - 6794
(2020/11/23)
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- 1,2-Dibromoethane and KI mediated α-acyloxylation of ketones with carboxylic acids
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The 1,2-dibromoethane- and KI-mediated α-acyloxylation of ketones is reported in moderate to good yield without the use of transition metals and strong oxidants. Various acids are well tolerated with wide functional group compatibility. An 1,2-dibromoethane- and KI-catalysed reaction mechanism is proposed based on the results of control experiments.
- Wang, Xujie,Li, Gangsheng,Yang, Yanan,Jiang, Jianshuang,Feng, Ziming,Zhang, Peicheng
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supporting information
p. 711 - 714
(2019/09/30)
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- Chemo- and Enantioselective Oxidative α-Azidation of Carbonyl Compounds
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We report high-performance I+/H2O2 catalysis for the oxidative or decarboxylative oxidative α-azidation of carbonyl compounds by using sodium azide under biphasic neutral phase-transfer conditions. To induce higher reactivity especially for the α-azidation of 1,3-dicarbonyl compounds, we designed a structurally compact isoindoline-derived quaternary ammonium iodide catalyst bearing electron-withdrawing groups. The nonproductive decomposition pathways of I+/H2O2 catalysis could be suppressed by the use of a catalytic amount of a radical-trapping agent. This oxidative coupling tolerates a variety of functional groups and could be readily applied to the late-stage α-azidation of structurally diverse complex molecules. Moreover, we achieved the enantioselective α-azidation of 1,3-dicarbonyl compounds as the first successful example of enantioselective intermolecular oxidative coupling with a chiral hypoiodite catalyst.
- Hattori, Yuhei,Ishihara, Kazuaki,Sahara, Naoto,Tsukahara, Mayuko,Uyanik, Muhammet
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supporting information
p. 17110 - 17117
(2020/08/10)
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- Visible-Light-Triggered Iodinations Facilitated by Weak Electrostatic Interaction of N-Heterocyclic Carbenes
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N-heterocyclic carbenes (NHCs) are well-known as ligands and organocatalysts, but there is no recognition for their catalytic role as a stabilizer through electrostatic interaction rather than electron donation. By utilizing the electrostatic interaction, we herein describe the success of a visible-light-triggered radical-radical cross-coupling of N-alkenoxypyridinium salts and NaI, giving a variety of α-iodo ketones. Computational studies characterize the stabilization role of NHCs.
- Chen, Xiang-Yu,Liu, Qiang,Lu, Yu,Sheng, He,Su, Xiao-Di,Wang, Zhi-Xiang
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supporting information
p. 7187 - 7192
(2020/10/02)
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- I2/PhI(OAc)2 Copromoted Amination Reaction: Synthesis of α-Dicarbonylsulfoximine Derivatives by Incorporating an Intact Dimethyl Sulfoxide
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An I2/PhI(OAc)2 copromoted strategy using dimethyl sulfoxide as an "S/C2/O" source for preparing α-dicarbonylsulfoximine derivatives is reported. This process involves oxidative coupling to construct a C-N bond and electrophilic amin
- Zhao, Peng,Wu, Xia,Geng, Xiao,Wang, Can,Zhou, You,Wu, Yan-Dong,Wu, An-Xin
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p. 8322 - 8329
(2019/06/27)
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- Direct Assembly of Polysubstituted Furans via C(sp3)?H Bond Functionalization by Using Dimethyl Sulfoxide as a Dual Synthon
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An unusual I2-mediated triple C(sp3)?H functionalization reaction between aryl methyl ketones and dimethyl sulfoxide to form polysubstituted furans has been developed. In this transformation, dimethyl sulfoxide functions as a dual synthon via C(sp3)?H functionalization with formation of two C?C bonds, one C?O bond, and one C?S bond in a one-step process. Iodine is crucial as promoter of the reaction, by which a number of ketones could be converted easily into 2,4,5-trisubstituted furans. This provides an extremely simple and expeditious approach to high-value-added, biologically significant O-heterocycles. Based on preliminary experiments, a plausible mechanism is proposed. (Figure presented.).
- Liu, Yufeng,Hu, Yuqun,Cao, Zhongzhong,Zhan, Xi,Luo, Weiping,Liu, Qiang,Guo, Cancheng
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p. 1084 - 1091
(2019/01/30)
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- Dimethyl Sulfoxide Oxygen Donor-Based Annulation of Ketones and Ammonium Persulfate: Regioselective Synthesis of 2,4-disubstituted Oxazoles
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An efficient protocol for the synthesis of substituted oxazoles via an annulation of ketones, DMSO, and ammonium is reported. DMSO is first found to serve as oxygen donor in annulation resulting in regioselective synthesis of 2,4-disubstituted oxazoles. With the optimized conditions in hand, 22 examples of 2,4-disubstituted oxazoles are obtained from readily available substrates. The protocol can be also applied in cross-condensation reactions between methyl ketones and non-methyl ketones resulting 4 examples of 2,4,5-trisubstituted oxazoles. Moreover, we have successfully applied the protocol into gram-scale representing good yields, that showing the potential practicality in organic synthesis. Based on control experiments and literature, a plausible reaction mechanism was proposed in our work. (Figure presented.).
- Cao, Zhongzhong,Lv, Huifang,Liu, Yufeng,Nie, Zhiwen,Liu, Haiping,Yang, Tonglin,Luo, Weiping,Liu, Qiang,Guo, Cancheng
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supporting information
p. 1632 - 1640
(2019/02/26)
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- Diversity-Oriented Synthesis of Complex Pyrrole-Based Architectures from Very Simple Starting Materials
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The build/couple/pair strategy was applied to the generation of 18 structurally diverse scaffolds built around pyrrole cores. The couple phase, involving the first application of a mechanochemical multicomponent reaction for this purpose, afforded pyrrole
- Leonardi, Marco,Estévez, Verónica,Villacampa, Mercedes,Menéndez, J. Carlos
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p. 2054 - 2074
(2019/03/13)
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- I2/CuCl2-promoted one-pot three-component synthesis of aliphatic or aromatic substituted 1,2,3-thiadiazoles
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An efficient I2/CuCl2-promoted one-pot three-component strategy for the construction of 1,2,3-thiadiazoles from aliphatic- or aromatic-substituted methyl ketones, p-toluenesulfonyl hydrazide, and potassium thiocyanate has been develo
- Wang, Can,Geng, Xiao,Zhao, Peng,Zhou, You,Wu, Yan-Dong,Cui, Yan-Fang,Wu, An-Xin
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supporting information
p. 8134 - 8137
(2019/07/15)
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- KI-Promoted Oxidative Coupling of Styrenes with Indoles under Metal-Free Conditions: Facile Access to C-3 Dicarbonyl Indoles
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A new and efficient method for the synthesis of C-3 dicarbonyl indoles via oxidative cross-coupling of styrenes with indoles under metal-free conditions has been developed. Moreover, a broad scope of C-3 dicarbonyl indoles in moderate to good yields were obtained, and a plausible mechanism is proposed based on control and isotope-labeling experiments.
- Fang, Zheng,Guo, Kai,Guo, Shiyu,He, Wei,Li, Xin,Liu, Chengkou,Yang, Zhao,Zhou, Bochao,Zhu, Ning
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p. 3511 - 3519
(2019/09/07)
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- Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives
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A new imidazolium-based poly(ionic liquid) has been synthesized and used as a robust heterogeneous catalyst for the preparation of phenacyl derivatives by an SN2 reaction of different phenacyl bromides with a broad range of nucleophiles. The products are obtained in high yields under mild conditions. The catalyst can be recycled efficiently.
- Kakesh,Sayyahi,Badri,Tahanpesar
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p. 1218 - 1220
(2019/07/16)
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- Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an i 2 /Cu(NO 3) 2 ?3H 2 O-Assisted Domino Sequence
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A new strategy has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available arylacetylenes and α-amino acids in the presence of Cu(NO 3) 2 ?3H 2 O and iodine. This reaction process involves the I 2 /Cu(NO 3) 2 ?3H 2 O-assisted transformation of arylacetylene to α-iodo acetophenone, Kornblum oxidation to phenylglyoxal, condensation to imine, decarboxylation/annulation/oxidation reaction sequence to approach 2,5-disubstituted oxazoles.
- Wang, Jungang,Cheng, Yan,Xiang, Jiachen,Wu, Anxin
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supporting information
p. 743 - 747
(2019/03/26)
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- Metal-Free, Oxidant-Free, and Controllable Graphene Oxide Catalyzed Direct Iodination of Arenes and Ketones
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A direct, metal-free, and oxidant-free method for the graphene oxide (GO)-catalyzed iodination of arenes and ketones with iodine in a neutral medium was explored. This iodination protocol was performed by using a simple technique to avoid the use of external metal catalysts and oxidants and harsh acidic/basic reaction conditions. In addition, by this method the degree of iodination could be controlled, and the reaction was scalable and compatible with air. This strategy opens a new field for GO-catalyzed chemistry and provides an avenue for the convenient direct iodination of arenes and ketones.
- Zhang, Jingyu,Li, Shiguang,Deng, Guo-Jun,Gong, Hang
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p. 376 - 380
(2017/12/07)
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- An AKAP-Lbc-RhoA interaction inhibitor promotes the translocation of aquaporin-2 to the plasma membrane of renal collecting duct principal cells
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Stimulation of renal collecting duct principal cells with antidiuretic hormone (arginine-vasopressin, AVP) results in inhibition of the small GTPase RhoA and the enrichment of the water channel aquaporin-2 (AQP2) in the plasma membrane. The membrane inser
- Schrade, Katharina,Tr?ger, Jessica,Eldahshan, Adeeb,Zühlke, Kerstin,Abdul Azeez, Kamal R.,Elkins, Jonathan M.,Neuenschwander, Martin,Oder, Andreas,Elkewedi, Mohamed,Jaksch, Sarah,Andrae, Karsten,Li, Jinliang,Fernandes, Joao,Müller, Paul Markus,Grunwald, Stephan,Marino, Stephen F.,Vuki?evi?, Tanja,Eichhorst, Jenny,Wiesner, Burkhard,Weber, Marcus,Kapiloff, Michael,Rocks, Oliver,Daumke, Oliver,Wieland, Thomas,Knapp, Stefan,Von Kries, Jens Peter,Klussmann, Enno
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- Metal-Free Synthesis of Furocoumarins: An Approach via Iodine-Promoted One-Pot Cyclization between 4-Hydroxycoumarins and Acetophenones
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A transition metal-free approach was developed to achieve substituted furocoumarins via an iodine-promoted one-pot cyclization between 4-hydroxycoumarins and acetophenones. High yields of furocoumarins were achieved in the presence of NH4OAc as
- Pham, Phuc H.,Nguyen, Que T. D.,Tran, Nhu K. Q.,Nguyen, Vu H. H.,Doan, Son. H.,Ha, Hiep Q.,Truong, Thanh,Phan, Nam T. S.
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p. 4431 - 4435
(2018/09/11)
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- Stereoselective synthesis of: E -3-(arylmethylidene)-5-(alkyl/aryl)-2(3 H)-furanones by sequential hydroacyloxylation-Mizoroki-Heck reactions of iodoalkynes
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A modular, stereoselective synthesis of E-3-(arylidene)-5-(alkyl/aryl)-2(3H)-furanones was developed. The methodology features regioselective addition of β-aryl acrylic acids to iodoacetylenes to furnish the Z-acyloxy iodoalkenes. A stereoselective 5-exo-trig Mizoroki-Heck reaction of the acyloxy iodoalkenes generates the target E-2(3H)-furanones. The approach was applied in a formal synthesis of the naturally occurring kinase inhibitor BE-23372M.
- Muthusamy, Gopinathan,Pansare, Sunil V.
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p. 7971 - 7983
(2018/11/21)
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- Iodide reagent controlled reaction pathway of iodoperoxidation of alkenes: A high regioselectivity synthesis of α- And β-iodoperoxidates under solvent-free conditions
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A highly atom economical, efficient and environmentally friendly iodoperoxidation of alkenes with tert-butyl hydroperoxide (TBHP) and iodide/iodine is reported in this paper. This method afforded a convenient path to obtain two different configurations of iodoperoxidates from the same starting materials. Notably, the regiodivergent iodoperoxidation reaction was achieved by using different iodide reagents. A series of control experiments were performed, which suggested the involvement of a radical pathway for the anti-Markovnikov type iodoperoxidates (α) in the combination of ammonium iodide (NH4I)/TBHP, and an active cationic iodine pathway for the Markovnikov type adduct (β) with iodine (I2) and TBHP.
- Gao, Xiaofang,Yang, Hongling,Cheng, Chen,Jia, Qi,Gao, Fang,Chen, Hongxiang,Cai, Qun,Wang, Chuangjian
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p. 2225 - 2230
(2018/05/30)
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- Iodine Monoacetate for Efficient Oxyiodinations of Alkenes and Alkynes
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A novel and inexpensive, environmentally friendly method for the preparation of iodine monoacetate is presented using iodine and Oxone in acetic acid/acetic anhydride. The reagent is used in a highly efficient approach for the regio- and diastereoselective iodo-acetoxylation of alkenes and alkynes in a simple one-pot process.
- Hokamp, Tobias,Storm, Alena Therese,Yusubov, Mekhman,Wirth, Thomas
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supporting information
p. 415 - 418
(2017/10/30)
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- Lewis Basicity of Water for a Selective Monodehalogenation of α,α-Dihalo Ketones to α-Halo Ketones and Mechanistic Study
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The Lewis base character of the greenest reagent water has been explored with regard to its nucleophilic property for an organic transformation. Utilizing this concept, a new strategy for the highly controlled and selective mono-dehalogenation of α,α-dihalo ketones has been discovered and is reported in this contribution. Extending this concept, the first direct conversion of propargylic acetates to the corresponding α-iodo ketones via α,α-dihalo ketones has also been efficiently achieved under metal-free conditions. During the latter process, water has been concurrently employed as a nucleophile and a Lewis base. This may be the first report of the employment of this type of dual reactivity of water in the context of organic synthesis. Control experiments support the involvement of the enolate as an intermediate during the monodehalogneation process. (Figure presented.).
- Sadhukhan, Santu,Baire, Beeraiah
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supporting information
p. 298 - 304
(2017/12/26)
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- An efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes leading to α-halomethyl ketones
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A highly efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes has been developed that proceeds smoothly under mild and neutral conditions and provides a general and practical route for the synthesis of a variety of α-halomethyl ketones with high atom-economy, excellent yield, and recyclability of the gold(I) catalyst. The presented method delivers an attractive alternative to classical α-halogenation of ketones.
- Hu, Sifan,Liu, Dayi,Yan, Chenyu,Cai, Mingzhong
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supporting information
p. 2983 - 2991
(2018/12/04)
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- Rapid and efficient one-pot microwave-assisted synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline in water–PEG-400
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An effective, expeditious, environmentally benign one-pot synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline from easily available starting materials as aromatic carbonyl compound, 2-amino pyridine, succinamide, and in situ g
- Jadhav, Santosh A.,Shioorkar, Mahesh G.,Chavan, Omprakash S.,Sarkate, Aniket P.,Shinde, Devanand B.
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supporting information
p. 285 - 290
(2017/02/10)
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- Mild and General Synthesis of Pyrrolo[2,1-a]isoquinolines and Related Polyheterocyclic Frameworks from Pyrrole Precursors Derived from a Mechanochemical Multicomponent Reaction
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The combination of a three-component, solvent-free pyrrole synthesis performed under mechanochemical conditions with a TMSOTf-catalyzed oxonium-mediated cyclization gave general access to pyrrolo[2,1-a]isoquinoline derivatives under very mild conditions.
- Leonardi, Marco,Villacampa, Mercedes,Menéndez, J. Carlos
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p. 2570 - 2578
(2017/03/14)
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- Expeditious one-pot multicomponent microwave-assisted green synthesis of substituted 2-phenyl Quinoxaline and 7-bromo-3-(4-ethylphenyl) pyrido[2,3-b]pyrazine in water–PEG and water–ethanol
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An eco-friendly, expeditious one-pot multicomponent synthesis of substituted 2-phenyl quinoxaline and 7-bromo-3-(4-ethylphenyl) pyrido[2,3-b]pyrazine 4a–k in water–ethanol from easily available starting materials as acetophenone 1, succinamide 2, aromatic
- Jadhav, Santosh A.,Sarkate, Aniket P.,Shioorkar, Mahesh G.,Shinde, Devanand B.
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p. 1661 - 1667
(2017/09/08)
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- High-speed vibration-milling-promoted synthesis of symmetrical frameworks containing two or three pyrrole units
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The pseudo-five-component reaction between -dicarbonyl compounds (2 molecules), diamines and α-iodoketones (2 molecules), prepared in situ from aryl ketones, was performed efficiently under mechanochemical conditions involving high-speed vibration milling
- Leonardi, Marco,Villacampa, Mercedes,Menéndez, J. Carlos
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supporting information
p. 1957 - 1962
(2017/09/27)
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- Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole with B(C6F5)3 Enabling the Electrophilic Cyanation of Silyl Enol Ethers
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The Lewis acidic activation of a hypervalent iodine reagent containing a transferable cyano group, 1-cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole (CDBX), with B(C6F5)3, to achieve the catalytic electrophilic cyanation of silyl enol ethers is presented. Mechanistic studies indicate that CDBX is activated through coordination of its cyano group to B(C6F5)3, thus enabling the electrophilic cyanation reaction to occur.
- Nagata, Takaya,Matsubara, Hiroki,Kiyokawa, Kensuke,Minakata, Satoshi
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supporting information
p. 4672 - 4675
(2017/09/12)
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- AuIII-Catalyzed Formation of α-Halomethyl Ketones from Terminal Alkynes
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A AuIII-catalyzed synthesis of α-halomethyl ketones from terminal alkynes was developed. This approach features excellent functional group compatibility and good yields for both aromatic and aliphatic terminal alkynes. The resulting α-halomethyl ketones were used to prepare heterocyclic indolizine structures. The plausible mechanism of the one-pot reaction is proposed.
- Xing, Yalan,Zhang, Ming,Ciccarelli, Sarah,Lee, John,Catano, Bryant
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supporting information
p. 781 - 785
(2017/02/15)
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- Water-controlled selective preparation of α-mono or α,α′-dihalo ketones: Via catalytic cascade reaction of unactivated alkynes with 1,3-dihalo-5,5-dimethylhydantoin
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The control of a reaction that can produce multiple products from the same starting material is a highly attractive and challenging concept in organic synthesis. An efficient protocol for the selective synthesis of α-mono or α,α′-dihalo ketones via a water-controlled three-component thiourea-catalyzed cascade reaction of unactivated alkynes, 1,3-dihalo-5,5-dimethylhydantoin and water has been developed. α-Monohaloketones were obtained in aqueous acetone at 45 °C; conversely, α,α′-dihalo ketones were formed with pure water as the sole solvent at room temperature.
- Wu, Chao,Xin, Xiu,Fu, Zhi-Min,Xie, Long-Yong,Liu, Kai-Jian,Wang, Zheng,Li, Wenyi,Yuan, Zhi-Hui,He, Wei-Min
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p. 1983 - 1989
(2017/06/09)
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- Regioselective oxidative cross-coupling of benzo[d] imidazo[2,1- b] thiazoles with styrenes: A novel route to C3-dicarbonylation
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A novel I2 promoted, highly efficient metal-free and peroxide-free greener domino protocol for the C3-dicarbonylation of benzo[d]imidazo[2,1-b]thiazoles (IBTs) with styrenes has been developed via oxidative cleavage of the C(sp2)-H bond, followed by C3-nucleophilic attack of IBT and oxidation. Interestingly, under these conditions 2-(benzo[d]imidazo[2,1-b]thiazol-2-yl)aniline gave the benzo[4′,5′]thiazolo[2′,3′:2,3]imidazo[4,5-c]quinoline derivative via oxidative cleavage of the C(sp2)-H bond, followed by Pictet-Spengler cyclization and aromatization. This method offers the advantages of broad substrate scope, ecofriendly feature and high atom economy apart from higher yields.
- Shaik, Siddiq Pasha,Sultana, Faria,Ravikumar,Sunkari, Satish,Alarifi, Abdullah,Kamal, Ahmed
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p. 7696 - 7704
(2017/09/27)
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- Intermolecular Tandem Addition/Esterification Reaction of Alkenes with Malonates Leading to γ-Lactones Mediated by Molecular Iodine under Visible Light Irradiation
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The iodine-mediated intermolecular C?C bond-forming/esterification reaction of various alkenes including α-olefins with malonates under irradiation using a compact fluorescent lamp has been developed to synthesize γ-lactones in moderate to excellent yield
- Maejima, Saki,Yamaguchi, Eiji,Itoh, Akichika
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supporting information
p. 3883 - 3887
(2017/09/18)
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- Direct Synthesis of α-Alkoxy Ketones by Oxidative C–O Bond Formation
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A convenient method to prepare α-alkoxy ketones has been developed by oxidative coupling of aryl methyl ketones and alcohols. With aqueous tert-butyl hydroperoxide (6.0 equiv.) as the oxidant, tetrabutylammonium iodide (20 mol-%) as the catalyst, and TsNHNH2(1.0 equiv.) as the additive, ketones underwent direct alkoxylation to give α-methoxy or α-ethoxy ketones in moderate to good yields.
- Yu, Hui,Xu, Yilan,Fang, Yan,Dong, Rui
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p. 5257 - 5262
(2016/11/13)
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- Metal-free oxidative cyclization of acetophenones with diamines: A facile access to phenylpyridines
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An efficient metal-free access to 2- and 3-phenylpyridines via oxidative coupling of acetophenones or phenylacetones with 1,3-diaminopropane has been described. The reaction involves shorter reaction time, excellent yields and a broad substrate scope. The reaction proceeds via the formation of imine, which further undergoes oxidative C-N bond cleavage, C-C bond formation and oxidation to give a pyridine skeleton. The quantum chemical calculations identified the transition state for the reaction and helped in tracing the reaction mechanism.
- Sharma, Rohit,Patel, Neha,Vishwakarma, Ram A.,Bharatam, Prasad V.,Bharate, Sandip B.
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supporting information
p. 1009 - 1012
(2016/01/16)
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- Dithiocarbamates as an efficient intermediate for the synthesis of 2-(alkylsulfanyl)thiazoles in water
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A simple, green and high-yielding procedure for the synthesis of 4-substituted-2-(alkylsulfanyl)thiazoles from the reaction of dithiocarbamates and α-halocarbonyl containing compounds in water is described. Also, a one-pot, two-step procedure for the synt
- Ziyaei Halimehjani, Azim,Hasani, Leila,Ali Alaei,Saidi, Mohammad R.
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supporting information
p. 883 - 886
(2016/02/05)
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- One pot synthesis of α-ketoamides from ethylarenes and amines: a metal free difunctionalization strategy
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One-pot and metal free synthesis of α-ketoamides has been described through in situ generation of aryl ketones from easily available ethylarenes followed by amidation with various amines. This multiple oxidation protocol involves catalytic I2-pyridine-TBHP (t-butyl hydroperoxide) mediated oxidative benzylic carbonylation and sequential NaI-TBHP mediated oxidative amidation without using any solvent.
- Ramanathan, Mani,Kuo, Chun-Kai,Liu, Shiuh-Tzung
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p. 11446 - 11453
(2016/12/16)
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- One pot synthesis of substituted imidazopyridines and thiazoles from styrenes in water assisted by NBS
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Heating of commercially available styrenes with NBS in water followed by reaction with 2-aminopyridines or thioamides afforded important heterocyclic scaffolds in a one pot procedure. The reaction proceeds via co-oxidant free, in situ formation of α-bromoketone using NBS as a bromine source as well as an oxidant followed by trapping with suitable nucleophiles to provide imidazopyridines and thiazoles.
- Shinde, Mahesh H.,Kshirsagar, Umesh A.
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p. 1455 - 1458
(2016/04/04)
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- One-Pot Aerobic Photooxidative Darzens Reaction from Styrene and Benzyl Alcohol via Phenacyl Iodide and Benzaldehyde by Using?- Iodine
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We report a one-pot protocol for the synthesis of α,β-epoxy ketones from benzyl alcohols and styrenes with molecular oxygen, visible light, and molecular iodine. This procedure involves simultaneous aerobic photooxidative transformation of a benzyl alcohol into a benzaldehyde and of a styrene into a phenacyl iodide, with a subsequent Darzens reaction in one pot. This is the first report of a one-pot oxidative Darzens reaction starting from benzyl alcohols and styrenes.
- Omura, Ryuji,Fujiya, Akitoshi,Yamaguchi, Eiji,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
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p. 3971 - 3975
(2016/11/11)
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- Integration of aqueous biphasic with magnetically recyclable systems: Polyethylene glycol-grafted Fe3O4 nanoparticles catalyzed phenacyl synthesis in water
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The present work trends to define an efficient phenacyl catalytic synthesis method employing a new nano-magnetite-supported organocatalyst. Polyethylene glycol (PEG) was bonded successfully onto silica coated ferrite and the resultant nanoparticles (PEG@SiO2@Fe3O4) characterized by fourier transform infrared spectroscopy (FT-IR), atomic force microscopy (AFM), thermal gravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray analysis (EDAX) and X-ray diffraction (XRD) that exhibited a good catalytic activity in the reaction. The nanoparticles could be easily separated from the reaction mixture by an external magnet and reused in seven reaction cycles without significant loss of activity.
- Amini, Atefeh,Sayyahi, Soheil,Saghanezhad, Seyyed Jafar,Taheri, Narges
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- First Catalyzed Hydration of Haloalkynes by a Recyclable Catalytic System
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The hydration of haloalkynes to give α-halomethyl ketones was achieved based on a combination of a Cu(OAc)2 catalyst and a TFA (trifluoroacetic acid) promoter. This is the first synthesis of chloro/bromo/iodo methyl ketones through a hydration reaction catalyzed by a recyclable catalytic system. The catalytic system has a wide substrate scope and excellent chemoselectivity, and the procedure can also be scaled up.
- Zou, Huaxu,He, Weibao,Dong, Qizhi,Wang, Ruijia,Yi, Niannian,Jiang, Jun,Pen, Dongming,He, Weimin
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p. 116 - 121
(2016/01/26)
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- Highly Efficient Synthesis of α-Halomethylketones via Ce(SO4)2/Acid Co-Catalyzed Hydration of Alkynes
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A general atom-economical approach for the synthesis of α-halomethyl ketones is demonstrated through Ce(SO4)2/acid co-catalyzed hydration of a wide range of haloalkynes. The reactions are conducted under convenient conditions and provide products with excellent regioselectivity in good to excellent yields, with broad substrate scope. This protocol is an alternative to conventional α-halogenation of ketones.
- Zou, Huaxu,Jiang, Jun,Yi, Niannian,Fu, Wenqiang,Deng, Wei,Xiang, Jiannan
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supporting information
p. 1251 - 1254
(2016/12/27)
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- Metal-free hydration of aromatic haloalkynes to α-halomethyl ketones
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A highly regioselective and efficient metal-free hydration of aromatic haloalkynes to α-halomethyl ketones using cheap tetrafluoroboric acid as catalyst is described. The protocol is conducted under convenient conditions and affords products in good to excellent yields, with broad substrate scope, including a variety of aromatic alkynyl chlorides, alkynyl bromides, and alkynyl iodides.
- Ye, Min,Wen, Yuelu,Li, Huifang,Fu, Yejuan,Wang, Qinghao
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supporting information
p. 4983 - 4986
(2016/10/21)
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- In(OTf)3/acid co-catalyzed hydration of 1-haloalkynes to α-halomethyl ketones
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A novel and efficient In(OTf)3and HOAc cooperatively catalyzed hydration of 1-haloalkynes is described. This method provides ready access to α-chloromethyl ketones, α-bromomethyl ketones and α-iodomethyl ketones in moderate to high yields from simple, inexpensive starting materials. A broad substrate scope is achieved, and the reaction is compatible with various functional groups, including alkoxy, trifluoromethyl, halide, hydroxyl, cyclohexyl, and heterocyclic groups.
- Zeng, Ming,Huang, Rui-Xue,Li, Wen-Yi,Liu, Xiao-Wen,He, Fu-Ling,Zhang, Yi-Yuan,Xiao, Fang
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p. 3818 - 3822
(2016/07/06)
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- I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C-H functionalization
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One-pot, atom-economic synthesis of quinoxalines has been achieved through generation of arylglyoxal from easily available ethylarenes, ethylenearenes and ethynearenes, and subsequent condensation with o-phenylenediamines. Catalytic I2 with TBHP as an oxidant in DMSO is the system of choice for this domino reaction involving C-H functionalization/oxidative cyclization. This metal-free, mechanistically distinct and functional group tolerant tandem approach could be a powerful complement to traditional approaches for the synthesis of quinoxalines. This journal is
- Vadagaonkar, Kamlesh S.,Kalmode, Hanuman P.,Murugan, Kaliyappan,Chaskar, Atul C.
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p. 5580 - 5590
(2015/02/05)
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