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Journal articles on the topic 'Electrophilic aldehydes'

Author: Grafiati

Published: 11 December 2022

Last updated: 31 July 2025

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1

Tola, Adesola J., Amal Jaballi, Hugo Germain, and Tagnon D. Missihoun. "Recent Development on Plant Aldehyde Dehydrogenase Enzymes and Their Functions in Plant Development and Stress Signaling." Genes 12, no. 1 (2020): 51. http://dx.doi.org/10.3390/genes12010051.

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Abiotic and biotic stresses induce the formation of reactive oxygen species (ROS), which subsequently causes the excessive accumulation of aldehydes in cells. Stress-derived aldehydes are commonly designated as reactive electrophile species (RES) as a result of the presence of an electrophilic α, β-unsaturated carbonyl group. Aldehyde dehydrogenases (ALDHs) are NAD(P)+-dependent enzymes that metabolize a wide range of endogenous and exogenous aliphatic and aromatic aldehyde molecules by oxidizing them to their corresponding carboxylic acids. The ALDH enzymes are found in nearly all organisms,

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2

Kočovský, Pavel, and Andrei V. Malkov. "Asymmetric synthesis: From transition metals to organocatalysis." Pure and Applied Chemistry 80, no. 5 (2008): 953–66. http://dx.doi.org/10.1351/pac200880050953.

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Umpolung in the allylation reaction is discussed with examples drawn from transition-metal-catalyzed allylic substitution (with the allylic unit acting as an electrophile) and Lewis base-catalyzed allylation of aldehydes with allyltrichlorosilane (with the allyl acting as a nucleophile). Iridium-catalyzed electrophilic allylation of O-nucleophiles has been employed in our new approach to C-nucleoside analogs, where the C-O bond (rather than C-C) was constructed stereospecifically. Variation of the absolute configuration in the starting segments allowed the synthesis of all four combinations of

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3

Li, Bin-Jie, Claudia EI-Nachef, and André M. Beauchemin. "Organocatalysis using aldehydes: the development and improvement of catalytic hydroaminations, hydrations and hydrolyses." Chemical Communications 53, no. 99 (2017): 13192–204. http://dx.doi.org/10.1039/c7cc07352f.

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4

Liang, Xin, Ruyi Qian, Dan Wang, Lijuan Liu, Chengliang Sun, and Xianyong Lin. "Lipid-Derived Aldehydes: New Key Mediators of Plant Growth and Stress Responses." Biology 11, no. 11 (2022): 1590. http://dx.doi.org/10.3390/biology11111590.

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Aldehydes, derivatives of lipids, are ubiquitously produced through non-enzymatic and enzymatic pathways in higher plants and participate in many physiological and biological processes. Increasing evidence demonstrates that aldehydes are involved in plants response to many abiotic stresses, such as light, drought, heat and nutrient deficiency. In plant cells, endogenously triggered or exogenously applied high concentrations of aldehydes can damage proteins and nucleic acid, disturb redox homeostasis, and consequently inhibit plant growth; therefore, they are considered cytotoxins. Aldehyde lev

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5

Senthil Kumar Raju, Archana Settu, Archana Thiyagarajan, Divya Rama, Praveen Sekar, and Shridharshini Kumar. "Synthetic approaches of medicinally important Schiff bases: An updated Review." World Journal of Advanced Research and Reviews 16, no. 3 (2022): 838–52. http://dx.doi.org/10.30574/wjarr.2022.16.3.1394.

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The Schiff base defined by an imine or azomethine (-CH= N-) group, is mostly synthesized by the condensation reaction of carbonyl compounds (Aldehyde or Ketone) with compounds consisting of amine moiety. Schiff bases are among the most chiefly used organic compounds, revealing a wide range of applications, such as electroluminescent effects, fluorescence properties, nonlinear optical and chemosensory properties. The typical Schiff bases are crystalline solids that are basic, although at least some of them combine with strong acids to generate insoluble salt. Schiff bases are widely used in the

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6

O'Brien, Nicholas S., and Adam McCluskey. "A Facile Microwave and SnCl2 Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones." Australian Journal of Chemistry 73, no. 12 (2020): 1176. http://dx.doi.org/10.1071/ch20101.

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An elegantly simple, facile, and robust approach to a scaffold of biological importance, 2,3-dihydroquinazolin-4(1H)-ones, is reported. A catalytic 1% SnCl2/microwave-mediated approach afforded access to pure material, collected by cooling and filtration after 20-min microwave irradiation at 120°C. A total of 41 analogues were prepared in isolated yields of 17–99%. This process was highly tolerant of aliphatic, aromatic, heterocyclic, and acyclic aldehydes, but furan, pyrrole, and thiophene aldehyde reactivity correlated with propensity towards electrophilic addition and/or Diels–Alder additio

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7

Kripli, Balázs, Miklós Szávuly, Flóra Viktória Csendes та József Kaizer. "Functional models of nonheme diiron enzymes: reactivity of the μ-oxo-μ-1,2-peroxo-diiron(iii) intermediate in electrophilic and nucleophilic reactions". Dalton Transactions 49, № 6 (2020): 1742–46. http://dx.doi.org/10.1039/c9dt04551a.

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8

Senthil, Kumar Raju, Settu Archana, Thiyagarajan Archana, Rama Divya, Sekar Praveen, and Kumar Shridharshini. "Synthetic approaches of medicinally important Schiff bases: An updated Review." World Journal of Advanced Research and Reviews 16, no. 3 (2022): 838–52. https://doi.org/10.5281/zenodo.7903785.

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The Schiff base defined by an imine or azomethine (-CH= N-) group, is mostly synthesized by the condensation reaction of carbonyl compounds (Aldehyde or Ketone) with compounds consisting of amine moiety. Schiff bases are among the most chiefly used organic compounds, revealing a wide range of applications, such as electroluminescent effects, fluorescence properties, nonlinear optical and chemosensory properties. The typical Schiff bases are crystalline solids that are basic, although at least some of them combine with strong acids to generate insoluble salt. Schiff bases are widely used in the

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9

Vera, Silvia, Aitor Landa, Antonia Mielgo, Iñaki Ganboa, Mikel Oiarbide та Vadim Soloshonok. "Catalytic Asymmetric α-Functionalization of α-Branched Aldehydes". Molecules 28, № 6 (2023): 2694. http://dx.doi.org/10.3390/molecules28062694.

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Aldehydes constitute a main class of organic compounds widely applied in synthesis. As such, catalyst-controlled enantioselective α-functionalization of aldehydes has attracted great interest over the years. In this context, α-branched aldehydes are especially challenging substrates because of reactivity and selectivity issues. Firstly, the transient trisubstituted enamines and enolates resulting upon treatment with an aminocatalyst or a base, respectively, would exhibit attenuated reactivity; secondly, mixtures of E- and Z-configured enamines/enolates may be formed; and third, effective face-

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10

Murugan, Rajendran, and Boreddy S. R. Reddy. "A New Protocol to Synthesize Di(indolyl)pyrazolyl Methanes Using H2PtCl6 as a Catalyst in Ionic Liquid: Synthesis of Novel 3-[1H-indol-3-yl(3-phenyl-1H-pyrazol-4-yl)methyl]-1H-indoles." Australian Journal of Chemistry 59, no. 4 (2006): 273. http://dx.doi.org/10.1071/ch05208.

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Biologically important di(indolyl)pyrazolyl methanes and their derivatives were synthesized in excellent yields by the electrophilic substitution of indole with pyrazolyl aldehydes catalyzed by H2PtCl6 in ionic liquid.

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11

Youn, Joo-Hack, Jinhwa Lee, and Jin Kun Cha. "Electrophilic Cyclizations of Vinylcyclopropanols to Tethered Aldehydes." Organic Letters 3, no. 18 (2001): 2935–38. http://dx.doi.org/10.1021/ol016490x.

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12

Zhao, Xian-Liang, Ke-Fang Yang, Xuan-Gan Liu, Chun-Lin Ye, Li-Wen Xu, and Guo-Qiao Lai. "Polyguanidine as a Highly Efficient and Reusable Catalyst for Knoevenagel Condensation Reactions in Water." Australian Journal of Chemistry 66, no. 4 (2013): 500. http://dx.doi.org/10.1071/ch12507.

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Polyguanidine is used as a novel and highly efficient catalyst in the Knoevenagel reaction of aldehydes with active methylene compounds in water to afford substituted electrophilic alkenes. This method is applicable for a wide range of aldehydes including aromatic and heterocyclic substrates. The polyguanidine catalyst can be recovered by simple filtration and reused many times for the aqueous Knoevenagel reaction without loss of activity.

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13

Monreal-Leyva, Isabel, Breanna Rose Attema, Nuri Bae, Haishi Cao, and Hector Palencia. "Benzoin condensation of aromatic aldehydes catalyzed by N-heterocyclic carbenes under mild conditions." European Journal of Chemistry 10, no. 1 (2019): 1–6. http://dx.doi.org/10.5155/eurjchem.10.1.1-6.1826.

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The benzoin condensation was used to evaluate the catalytic activity of different N-heterocyclic carbenes as a function of their structure and N-substituents. There is a correlation between the length of an N-alkyl substituent and its performance as an organocatalyst. Heteroaromatic aldehydes were found to be the most reactive, among the screened substrates, finishing the reaction in 30 minutes, with almost quantitative yields. On the other hand, p-nitrobenzaldehyde, a strongly electrophilic aldehyde, was the least reactive. Electronic effects have little influence on the reaction yield but st

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14

Rajitha, Bavanthula, Penthala Narsimha Reddy, Buridapad Sunil Kumar, Neeladri Sreenivasulu, and Yerram Reddy Thirupathi Reddy. "VCl3 Catalysed Efficient Synthesis of Bis(indolyl)methanes." Journal of Chemical Research 2005, no. 4 (2005): 222–23. http://dx.doi.org/10.3184/0308234054213384.

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VCl3 is found to be an efficient catalysts for the electrophilic substitution reaction of indoles with aromatic aldehydes in dichloromethane to afford the corresponding bis(indolyl)methanes in excellent yields at room temperature.

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15

Behbahani, Kargar, and Masoumeh Sasani. "Facile synthesis of bis(indolyl)methanes using iron(III) phosphate." Journal of the Serbian Chemical Society 77, no. 9 (2012): 1157–63. http://dx.doi.org/10.2298/jsc110727203b.

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A new, convenient and high yielding procedure for the preparation of bis(indolyl)methanes in glycerol by electrophilic substitution reaction of indole with aldehydes in the presence of catalytic amount of FePO4 (5.0 mol%) as a highly stable and reusable catalyst is described.

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16

Wang, Yi-Ming, Austin C. Durham, and Yidong Wang. "Redox-Neutral Propargylic C–H Functionalization by Using Iron Catalysis." Synlett 31, no. 18 (2020): 1747–52. http://dx.doi.org/10.1055/s-0040-1707271.

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AbstractIn spite of their rich stoichiometric chemistry, cyclopentadienyliron(II) dicarbonyl complexes are rarely used as catalysts in organic synthesis. Inspired by precedents in the chemistry of cationic olefin complexes and neutral allylmetal species, our group has developed a coupling of alkynes or alkenes with aldehydes and other carbonyl electrophiles to give homopropargylic and homoallylic alcohols, respectively, by using a substituted cyclopentadienyliron(II) dicarbonyl complex as the catalyst. In this article, we first contextualize this development within the conceptual background of

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17

Lee, Seung Eun, та Yong Seek Park. "Role of Lipid Peroxidation-Derivedα,β-Unsaturated Aldehydes in Vascular Dysfunction". Oxidative Medicine and Cellular Longevity 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/629028.

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Vascular diseases are the most prominent cause of death, and inflammation and vascular dysfunction are key initiators of the pathophysiology of vascular disease. Lipid peroxidation products, such as acrolein and otherα,β-unsaturated aldehydes, have been implicated as mediators of inflammation and vascular dysfunction.α,β-Unsaturated aldehydes are toxic because of their high reactivity with nucleophiles and their ability to form protein and DNA adducts without prior metabolic activation. This strong reactivity leads to electrophilic stress that disrupts normal cellular function. Furthermore,α,β

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18

Dong, Jianyang, Zhen Wang, Xiaochen Wang, Hongjian Song, Yuxiu Liu, and Qingmin Wang. "Ketones and aldehydes as alkyl radical equivalents for C─H functionalization of heteroarenes." Science Advances 5, no. 10 (2019): eaax9955. http://dx.doi.org/10.1126/sciadv.aax9955.

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The polar nature of the C═O bond commonly allows it to undergo direct attack by nucleophiles at the electrophilic carbon atom in which ketones and aldehydes act as alkyl carbocation equivalents. In contrast, transformations in which ketones and aldehydes act as alkyl radical equivalents (generated in carbonyl carbon) are unknown. Here, we describe a new catalytic activation mode that combines proton-coupled electron transfer (PCET) with spin-center shift (SCS) and enables C─H alkylation of heteroarenes using ketones and aldehydes as alkyl radical equivalents. This transformation proceeded via

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19

Hassaneen, Huwaida M. E., Tayseer A. Abdallah, Hamdi M. Hassaneen, and Mohamed H. Elnagdi. "Functionally Substituted Enamines as Building Blocks in Heterocyclic Synthesis: Reactivity of Glyoxal Diphenylhydrazone toward Electrophilic Reagents." Journal of Chemical Research 2005, no. 11 (2005): 729–32. http://dx.doi.org/10.3184/030823405774909441.

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Glyoxalbis(phenylhydrazone) 1a reacts with aromatic aldehydes and secondary amines to yield either propan-1,2-dialdiphenylhydrazones 2 or arylazopyrazoles 7 depending on the nature of utilised aldehyde. The reactivity of 1a with phosphorus oxychloride (POCl3) and dimethylformamide (DMF) (Vilsmeier reaction) afforded the cinnolin-3-carbaldehyde phenylhydrazone 11. Compound 1a afforded also the tribenzoyl derivative 16 on treatment with benzoyl chloride. Only the diacetyl derivative 17 was produced on refluxing 1a in acetic anhydride. The diphenylhydrazone 20 was produced on treatment of 19, pre

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20

Barrera, Giuseppina, Stefania Pizzimenti, Martina Daga, et al. "Lipid Peroxidation-Derived Aldehydes, 4-Hydroxynonenal and Malondialdehyde in Aging-Related Disorders." Antioxidants 7, no. 8 (2018): 102. http://dx.doi.org/10.3390/antiox7080102.

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Among the various mechanisms involved in aging, it was proposed long ago that a prominent role is played by oxidative stress. A major way by which the latter can provoke structural damage to biological macromolecules, such as DNA, lipids, and proteins, is by fueling the peroxidation of membrane lipids, leading to the production of several reactive aldehydes. Lipid peroxidation-derived aldehydes can not only modify biological macromolecules, by forming covalent electrophilic addition products with them, but also act as second messengers of oxidative stress, having relatively extended lifespans.

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21

Rao, Narra Laxmana, Kolakuluri Chaguruswamy, Mohan Lakshmi Punna Rao Alapati, and Vemulapalli Vandana. "Non-metallic catalyzed synthesis of substituted [3,3':3',3''-terindolin]-2'-ones and 3,3'- (phenylmethylene)bis(1H-indoles)." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 02 (2025): 209. https://doi.org/10.59467/ijhc.2025.35.209.

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Camphor sulfonic acid (CSA) was found to be a low-cost, readily available, and efficient non-metallic catalyst for the electrophilic substitution reaction of a substituted indole with various isatins and aryl aldehydes in 30% MeCN-H2O solvent to afford the corresponding [3,3':3',3''-terindolin]-2'-one and 3,3'-(phenylmethylene)bis(1H-indole) with higher yields at room temperature. This new procedure has remarkable features, such as experimental simplicity, less expensive, high conversions, good to excellent yields, shorter reaction times, and simple work-up procedures.. KEYWORDS :Camphor sulfo

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22

Borodina, O., A. Novikov, G. Zyryanov, and E. Bartashevich. "Theoretical evaluation of phenyl-substituted aziridines, azirines and epoxides reactivity." Bulletin of the South Ural State University series "Chemistry" 15, no. 4 (2023): 149–59. http://dx.doi.org/10.14529/chem230406.

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The reactivity of three-membered heterocycles such as phenyl-substituted aziridines, azirines, epoxides was studied in comparison with styrenes, azomethines and carbonyl com-pounds which are most often used in organic synthesis in nucleophilic and electrophilic reactions. In accordance with electronic reactivity indices of nucleophilicity and electrophilicity calculated on the base of DFT approach, the substituted molecules of azirines, aziridines, and epoxides ex-hibit the similar reactivity to aldehydes and styrenes. In all cases, our predictions were checked against the experimental observa

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23

Costa, Paulo R. R., Alcides J. M. da Silva, Mário L. A. A. Vasconcellos, Cláudio C. Lopes, and Rosangela S. C. Lopes. "Variable Chemo-selective Electrophilic Attack on Silylated Aromatic Aldehydes." Synlett 1996, no. 08 (1996): 783–84. http://dx.doi.org/10.1055/s-1996-5530.

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24

Youn, Joo-Hack, Jinhwa Lee, and Jin Kun Cha. "ChemInform Abstract: Electrophilic Cyclizations of Vinylcyclopropanols to Tethered Aldehydes." ChemInform 33, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.200202046.

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25

Banothu, Janardhan, Rajitha Gali, Ravibabu Velpula, Rajitha Bavantula, and Peter A. Crooks. "An Eco-Friendly Improved Protocol for the Synthesis of Bis(3-indolyl)methanes Using Poly(4-vinylpyridinium)hydrogen Sulfate as Efficient, Heterogeneous, and Recyclable Solid Acid Catalyst." ISRN Organic Chemistry 2013 (September 2, 2013): 1–5. http://dx.doi.org/10.1155/2013/616932.

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Highly efficient and eco-friendly protocol for the synthesis of bis(3-indolyl)methanes by the electrophilic substitution reaction of indole with aldehydes catalyzed by poly(4-vinylpyridinium)hydrogen sulfate was described. Excellent yields, shorter reaction times, simple work-up procedure, avoiding hazardous organic solvents, and reusability of the catalyst are the most obvious advantages of this method.

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26

Chatterjee, Paresh Nath, Dipankar Paul, Micky Lanster Sawkmie, Arun Kumar Sinha, and Snehadrinarayan Khatua. "Synthesis, characterization of active Sn(0), and its application in selective propargylation of aldehyde at room temperature in water." Canadian Journal of Chemistry 97, no. 1 (2019): 29–36. http://dx.doi.org/10.1139/cjc-2017-0745.

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Active Sn(0) particles are synthesized in high yields by the chemical reduction of the blue–black stannous oxide using freshly prepared sodium stannite solution as reducing agent at 40 °C and 60 °C. The Sn(0) particles are characterized using powder XRD, SEM, and DSC. The as-synthesized Sn(0) particles are applied as reagent for the regioselective synthesis of homopropargyl alcohols from propargyl bromide and aldehydes in distilled water at room temperature (in 50%–84% yields). No assistance of heat, microwave, ultrasound, organic co-solvent, co-reagent, or inert atmosphere is required for thi

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27

Singh, Shailesh, Jyoti Tiwari, Deepali Jaiswal, et al. "Nucleophilic Acylation with Aromatic Aldehydes to 2 Bromoacetonitrile: An Umpolung Strategy for the Synthesis of Active Methylene Compounds." Current Organic Synthesis 17, no. 7 (2020): 518–24. http://dx.doi.org/10.2174/1570179417666200615153536.

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Background: A novel one-pot N-heterocyclic carbene (NHC)-catalysed acylation of 2- bromoacetonitrile with aromatic aldehydes is reported. The protocol involves carbonyl umpolung reactivity of aldehydes in which the carbonyl carbon attacks nucleophilically (as d1 nucleophile) on the electrophilic terminal of 2-bromoacetonitrile to afford 3-aryl-3-oxopropanenitrile. The salient features of this procedure are short reaction time, operational simplicity, ambient temperature, no by-product formation and high yields. Materials and Methods: A flame-dried round bottom flask was charged with Imidazoliu

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28

Zayed, Salem E., Eiman I. Abou Elmaged, Saud A. Metwally та Mohamed H. Elnagdi. "Reactions of six-membered heterocyclic β-enaminonitriles with electrophilic reagents". Collection of Czechoslovak Chemical Communications 56, № 10 (1991): 2175–82. http://dx.doi.org/10.1135/cccc19912175.

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The nitriles I reacted with acetylacetone and with ethyl acetoacetate to afford 2-amino-3-cyano-4H-pyran derivatives. They reacted further to yield pyranopyridine derivatives. The reaction of V with acetylacetone afforded the pyridinethione VIII. This afforded, reacting with aromatic aldehydes or with cinnamonitriles quinoline derivatives XVII.

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29

Senthil Kumar Raju, Archana Settu, Archana Thiyagarajan, Divya Rama, Praveen Sekar, and Shridharshini Kumar. "Biological applications of Schiff bases: An overview." GSC Biological and Pharmaceutical Sciences 21, no. 3 (2022): 203–15. http://dx.doi.org/10.30574/gscbps.2022.21.3.0484.

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Schiff bases are the compounds containing the azomethine group (-HC=N-). They are formed by the condensation of ketones or aldehydes with a primary amine. Formation of Schiff base generally takes place under acid/base catalysis or with heat. The common Schiff bases are crystalline solids, which are basic but at least some form insoluble salts with strong acids. Schiff bases are used as intermediates for the synthesis of amino acids or as ligands for the preparation of metal complexes having a series of different structures. The electrophilic carbon and nucleophilic nitrogen in the C=N imine bo

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30

Senthil, Kumar Raju, Settu Archana, Thiyagarajan Archana, Rama Divya, Sekar Praveen, and Kumar Shridharshini. "Biological applications of Schiff bases: An overview." GSC Biological and Pharmaceutical Sciences 21, no. 3 (2022): 203–15. https://doi.org/10.5281/zenodo.7654212.

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Schiff bases are the compounds containing the azomethine group (-HC=N-). They are formed by the condensation of ketones or aldehydes with a primary amine. Formation of Schiff base generally takes place under acid/base catalysis or with heat. The common Schiff bases are crystalline solids, which are basic but at least some form insoluble salts with strong acids. Schiff bases are used as intermediates for the synthesis of amino acids or as ligands for the preparation of metal complexes having a series of different structures. The electrophilic carbon and nucleophilic nitrogen in the C=N imine bo

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31

Mayr, Herbert, Sami Lakhdar, Biplab Maji, and Armin R. Ofial. "A quantitative approach to nucleophilic organocatalysis." Beilstein Journal of Organic Chemistry 8 (September 5, 2012): 1458–78. http://dx.doi.org/10.3762/bjoc.8.166.

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The key steps in most organocatalytic cyclizations are the reactions of electrophiles with nucleophiles. Their rates can be calculated by the linear free-energy relationship log k(20 °C) = s N(E + N), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the solvent-dependent nucleophilicity (N) and sensitivity (s N) parameters. Electrophilicity parameters in the range –10 < E < –5 were determined for iminium ions derived from cinnamaldehyde and common organocatalysts, such as pyrrolidines and imidazolidinones, by studying the rates of their rea

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32

Gharat, Vaishnav D., and Vishvanath D. Patil. "Multicomponent synthesis of pyrazole-3-one under mild conditions using an effective novel ceria-doped copper nanocatalyst." Research Journal of Chemistry and Environment 29, no. 1 (2024): 52–60. https://doi.org/10.25303/291rjce052060.

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Synthesis of pyrazole-3-one derivative was successfully catalyzed by a copper nanocatalyst that had been doped with cerium. With outstanding yields of pyrazol- 3-one derivatives, this approach has been applied to a wide range of substrates including electrophilic and sterically hindered aromatic aldehydes. The remarkable selectivity under mild conditions of this commercially available inexpensive catalyst is an attractive feature of this method.

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33

Li, Jie, Lei Liu, Zhao Zhang, Yucheng Wang, and Yan Zhang. "Electrophilic Amination with Anthranils through Thioamide-Assisted Cobalt(III)-Catalyzed C(sp3)–H Activation." Synthesis 52, no. 24 (2020): 3881–90. http://dx.doi.org/10.1055/s-0039-1690087.

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Cobalt(III)-catalyzed electrophilic amination of inert C(sp3)–H bonds of weakly coordinating thioamides with readily accessible anthranil derivatives was accomplished under mild conditions, with good functional group tolerance, thus providing various amino aldehydes and amino ketones. Moreover, our protocol with the versatile [Cp*Co(MeCN)3][SbF6]2 features excellent atom-economy and oxidant-free conditions, and allows facile late-stage functionalization.

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34

Desmarchelier, Alaric, Hasret Yalgin, Vincent Coeffard, Xavier Moreau та Christine Greck. "Primary amine catalyzed electrophilic amination of α,α-disubstituted aldehydes". Tetrahedron Letters 52, № 34 (2011): 4430–32. http://dx.doi.org/10.1016/j.tetlet.2011.06.063.

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35

Appel, Roland, and Herbert Mayr. "Quantification of the Electrophilic Reactivities of Aldehydes, Imines, and Enones." Journal of the American Chemical Society 133, no. 21 (2011): 8240–51. http://dx.doi.org/10.1021/ja200820m.

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36

COSTA, P. R. R., A. J. M. DA SILVA, M. L. A. A. VASCONCELLOS, C. C. LOPES, and R. S. C. LOPES. "ChemInform Abstract: Variable Chemoselective Electrophilic Attack on Silylated Aromatic Aldehydes." ChemInform 27, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.199650070.

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37

Esposti, Silvia, Daniele Dondi, Maurizio Fagnoni, and Angelo Albini. "Acylation of Electrophilic Olefins through Decatungstate-Photocatalyzed Activation of Aldehydes." Angewandte Chemie 119, no. 14 (2007): 2583–86. http://dx.doi.org/10.1002/ange.200604820.

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38

Esposti, Silvia, Daniele Dondi, Maurizio Fagnoni, and Angelo Albini. "Acylation of Electrophilic Olefins through Decatungstate-Photocatalyzed Activation of Aldehydes." Angewandte Chemie International Edition 46, no. 14 (2007): 2531–34. http://dx.doi.org/10.1002/anie.200604820.

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39

Bardajee, Ghasem, and Farnaz Jafarpour. "Bi(NO3)3 · 5H2O mediated synthesis of 4,4′-diaminotriarylmethane leuco malachite compounds under solvent-free conditions." Open Chemistry 7, no. 1 (2009): 138–42. http://dx.doi.org/10.2478/s11532-008-0100-x.

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AbstractIn this report, we described the synthesis and characterization of a variety of diaminotriarylmethane derivatives with dimethylamino functional groups. These compounds were synthesized by the tandem regio-selective electrophilic aromatic substitution reaction of N,N-dimethylaniline with aryl aldehydes to form the corresponding diaminotriarylmethane compounds. In our strategy, Bi(NO3)3 was used as a catalyst under solvent free conditions to afford the desired products in good to excellent yields.

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Olyaei, Abolfazl, Mohsen Vaziri, Reza Razeghi, Shams Bahareh, and Hasan Bagheri. "Novel approach to bis(indolyl)methanes using nickel nanoparticles as a reusable catalyst under solvent-free conditions." Journal of the Serbian Chemical Society 78, no. 4 (2013): 463–68. http://dx.doi.org/10.2298/jsc120506076o.

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A nanosized Nickel as catalyst has been developed for the electrophilic substitution reactions of indole with variousaromatic aldehydes under solvent-free conditions to afford the corresponding bis(indolyl)methanes in high to excellent yields. The described method has promising features such as no hazardous organic solvents or catalysts, short reaction time, high product yields, simple work-up procedure, reusable catalyst and easy product separation without further purification with column chromatography.

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Rivas-Loaiza, Juan A., Carlos E. Reyes-Escobedo, Yliana Lopez, Susana Rojas-Lima, Juan Pablo García-Merinos, and Heraclio López-Ruiz. "(Thio)urea-catalyzed Friedel-Crafts Reaction: Synthesis of Bis(indolyl)- methanes." Letters in Organic Chemistry 16, no. 12 (2019): 959–68. http://dx.doi.org/10.2174/1570178616666190222150915.

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:Bis(indolyl)methane derivatives (BIMs) were synthesized in moderate to good yields by (thio)urea catalyzed electrophilic substitution of indole (2) with various aldehydes 1. Reactions were performed under conventional and microwave (MW) heating, either using 1,2-dichloroetane as solvent or without solvent. The procedure using microwave heating was also applied to the synthesis of the natural products vibrindole A (3n), arsindoline A (3i), arundine (3o) and tris(1H-indol-3-yl)methane (3j). Additionally, the synthesis of streptindole was carried out via intermediate 3g. This methodology is well

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Hasaninejad, Alireza, Abdolkarim Zare, Hashem Sharghi, et al. "A solvent-free protocol for facile condensation of indoles with carbonyl compounds using silica chloride as a new, highly efficient, and mild catalyst." Canadian Journal of Chemistry 85, no. 6 (2007): 416–20. http://dx.doi.org/10.1139/v07-051.

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A simple and efficient solvent-free procedure for the preparation of bis(indolyl)methanes via electrophilic substitution reactions of indoles with aldehydes and ketones is described. The reactions took place in the presence of a catalytic amount of silica chloride at room temperature. The advantages of this method are high yields, short reaction times, low cost, and compliance with green-chemistry protocols.Key words: silica chloride, indole, carbonyl compound, solvent-free, bis(indolyl)methane.

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Zoli, Luca, and Pier Giorgio Cozzi. "Electrophilic Activation of Aldehydes “On Water”: A Facile Route to Dipyrromethanes." ChemSusChem 2, no. 3 (2009): 218–20. http://dx.doi.org/10.1002/cssc.200900023.

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Kumar, Pradeep, та Brijesh Sharma. "Proline-Catalyzed Asymmetric α-Amination in the Synthesis of Bioactive Molecules". Synlett 29, № 15 (2018): 1944–56. http://dx.doi.org/10.1055/s-0037-1610022.

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The direct α-amination of carbonyl compounds using organocatalysts represents a powerful and atom-economical tool for asymmetric C–N bond formation. We describe a complete account of α-functionalization of carbonyl compounds, through iterative sequential α-aminoxylation/amination using electrophilic O and N sources, as well as sequential α-amination/HWE reaction for enantio- and diastereoselective synthesis of both syn- and anti-1,3-aminoalcohols and 1,3-diamines. Additionally this protocol is further extended for the easy construction of alkaloids such as indolizidine, pyrrolizidine, and quin

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Desmarchelier, Alaric, Hasret Yalgin, Vincent Coeffard, Xavier Moreau та Christine Greck. "ChemInform Abstract: Primary Amine Catalyzed Electrophilic Amination of α,α-Disubstituted Aldehydes." ChemInform 42, № 46 (2011): no. http://dx.doi.org/10.1002/chin.201146049.

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STETTER, H., and H. KUHLMANN. "ChemInform Abstract: The Catalyzed Nucleophilic Addition of Aldehydes to Electrophilic Double Bonds." ChemInform 23, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199203295.

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Ji, Kegong, Jonathan Nelson та Liming Zhang. "Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes". Beilstein Journal of Organic Chemistry 9 (24 вересня 2013): 1925–30. http://dx.doi.org/10.3762/bjoc.9.227.

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Gold-catalyzed intermolecular oxidation of carboxylates of primary or secondary propargylic alcohols are realized with excellent regioselectivity, which is ascribed to inductive polarization of the C–C triple bond by the electron-withdrawing carboxy group. The gold carbene intermediates thus generated undergo selective 1,2-acyloxy migration over a 1,2-C–H insertion, and the selectivities could be dramatically improved by the use of a P,S-bidentate ligand, which is proposed to enable the formation of tris-coordinated and hence less electrophilic gold carbene species. α-Carboxy α,β-unsaturated k

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Zou, Song, Sheng Wang, and Chanjuan Xi. "ROTf-induced annulation of heteroatom reagents and unsaturated substrates leading to cyclic compounds." Royal Society Open Science 5, no. 11 (2018): 181389. http://dx.doi.org/10.1098/rsos.181389.

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The development of metal-free organic reactions is one of the hotspots in the synthesis of cyclic compounds. ROTf (alkyl trifluoromethanesulfonates), due to their good electrophilicity, are powerful alkylating reagents at heteroatoms such as nitrogen, oxygen, sulfur and phosphorus to induce an electrophilic centre for carbon–carbon or carbon–heteroatom bond formation. Inspired by this chemistry, a variety of research concentrating on heterocycles synthesis has been carried out. In this review, we mainly summarize the ROTf-induced annulation of heteroatom reagents such as nitriles, carbodiimide

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Aeyad, Tahani, Jason Williams, Anthony Meijer, and Iain Coldham. "Lithiation–Substitution of N-Boc-2-phenylazepane." Synlett 28, no. 20 (2017): 2765–68. http://dx.doi.org/10.1055/s-0036-1590857.

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Preparation of 2,2-disubstituted azepanes was accomplished from N-tert-butoxy(N-Boc)-2-phenylazepane by treatment with butyllithium then electrophilic quench. The lithiation was followed by in situ ReactIR spectroscopy and the rate of rotation of the carbamate was determined by variable temperature (VT)-NMR spectroscopy and by DFT studies. Most electrophiles add α to the nitrogen atom but cyanoformates and chloroformates gave ortho-substituted products. Cyclic carbamates were formed from an aldehyde or ketone electrophile. Kinetic resolution with sparteine was only poorly selective. Removal of

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França, Carla Giometti, Denise Gradella Villalva, and Maria Helena Andrade Santana. "Oxi-HA/ADH Hydrogels: A Novel Approach in Tissue Engineering and Regenerative Medicine." Polysaccharides 2, no. 2 (2021): 477–96. http://dx.doi.org/10.3390/polysaccharides2020029.

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Hyaluronic acid (HA) is a natural polyelectrolyte abundant in mammalian connective tissues, such as cartilage and skin. Both endogenous and exogenous HA produced by fermentation have similar physicochemical, rheological, and biological properties, leading to medical and dermo-cosmetic products. Chemical modifications such as cross-linking or conjugation in target groups of the HA molecule improve its properties and in vivo stability, expanding its applications. Currently, HA-based scaffolds and matrices are of great interest in tissue engineering and regenerative medicine. However, the partial

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