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Journal articles on the topic 'Electrophilic reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Zheng, Danqing, Mo Chen, Liangqing Yao, and Jie Wu. "A general route to sulfones via insertion of sulfur dioxide promoted by cobalt oxide." Organic Chemistry Frontiers 3, no. 8 (2016): 985–88. http://dx.doi.org/10.1039/c6qo00099a.

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A cobalt-promoted coupling reaction of triethoxysilanes, sulfur dioxide, and electrophiles is developed. Different electrophilic partners including alkyl bromides, iodonium salts, and electron-poor (hetero)aryl chlorides work well under the standard conditions.

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2

Hubbard, Abigail, Takao Okazaki, and Kenneth K. Laali. "Chlorination of Aromatics with Trichloroisocyanuric Acid (TCICA) in Brønsted-Acidic Imidazolium Ionic Liquid [BMIM(SO3H)][OTf]: an Economical, Green Protocol for the Synthesis of Chloroarenes." Australian Journal of Chemistry 60, no. 12 (2007): 923. http://dx.doi.org/10.1071/ch07261.

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A survey study on electrophilic chlorination of aromatics with trichloroisocyanuric acid (TCICA) in Brønsted-acidic imidazolium ionic liquid [BMIM(SO3H)][OTf] is reported. The reactions are performed under very mild conditions (at ~50°C) and give good to excellent yields, depending on the substrates. Chemoselectivity for mono- v. dichlorination can be tuned by changing the arene-to-TCICA ratio and the reaction time. The survey study and competitive experiments suggest that triprotonated/protosolvated TCICA is a selective/moderately reactive transfer-chlorination electrophile. Density functional theory was used as guide to obtain further insight into the nature of the chlorination electrophile and the transfer-chlorination step.

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3

Ismailov, Ismail E., Ivaylo K. Ivanov, and Valerij Ch Christov. "Trifunctionalized Allenes. Part IV. Cyclization Reactions of 4-Phosphorylated 5-Hydroxyhexa-2,3-dienoates." Letters in Organic Chemistry 17, no. 9 (September 17, 2020): 726–33. http://dx.doi.org/10.2174/1570178617666200225104238.

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This manuscript focuses on the reactions of 4-phosphorylated 5-hydroxyhexa-2,3-dienoates with protected or unprotected hydroxy groups involving 5-endo-trig cyclizations. Reactions with electrophiles result in mixtures of the 2,5-dihydro-1,2-oxaphosphole-5-carboxylates and the 5-phosphorylfuran- 2(5H)-ones by competitive electrophilic cyclization due to the neighboring phosphonate (phosphine oxide) and the carboxylate groups participation. 4-Phosphorylated 5-hydroxyhexa-2,3-dienoates were smoothly transformed into the corresponding 4-phosphoryl-2,5-dihydrofuran-2-carboxylates by using 5 mol % of a silver salt as a catalyst in the 5-endo-trig cycloisomerization reaction.

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4

Gansäuer, Andreas, Meriam Seddiqzai, Tobias Dahmen, Rebecca Sure, and Stefan Grimme. "Computational study of the rate constants and free energies of intramolecular radical addition to substituted anilines." Beilstein Journal of Organic Chemistry 9 (August 8, 2013): 1620–29. http://dx.doi.org/10.3762/bjoc.9.185.

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The intramolecular radical addition to aniline derivatives was investigated by DFT calculations. The computational methods were benchmarked by comparing the calculated values of the rate constant for the 5-exo cyclization of the hexenyl radical with the experimental values. The dispersion-corrected PW6B95-D3 functional provided very good results with deviations for the free activation barrier compared to the experimental values of only about 0.5 kcal mol−1 and was therefore employed in further calculations. Corrections for intramolecular London dispersion and solvation effects in the quantum chemical treatment are essential to obtain consistent and accurate theoretical data. For the investigated radical addition reaction it turned out that the polarity of the molecules is important and that a combination of electrophilic radicals with preferably nucleophilic arenes results in the highest rate constants. This is opposite to the Minisci reaction where the radical acts as nucleophile and the arene as electrophile. The substitution at the N-atom of the aniline is crucial. Methyl substitution leads to slower addition than phenyl substitution. Carbamates as substituents are suitable only when the radical center is not too electrophilic. No correlations between free reaction barriers and energies (ΔG ‡ and ΔG R) are found. Addition reactions leading to indanes or dihydrobenzofurans are too slow to be useful synthetically.

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5

Slivka, Mikhailo, and Mikhailo Onysko. "The Use of Electrophilic Cyclization for the Preparation of Condensed Heterocycles." Synthesis 53, no. 19 (May 19, 2021): 3497–512. http://dx.doi.org/10.1055/s-0040-1706036.

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AbstractCondensed heterocycles are well-known for their excellent biological effects and they are undeniably important compounds in organic chemistry. Electrophilic cyclization reactions are widely used for the synthesis of mono-heterocyclic compounds. This review highlights the utility of electrophilic cyclization reactions as an effective generic tool for the synthesis of various condensed heterocycles containing functional groups that are able to undergo further chemical transformations, such as nucleophilic substitution, elimination, re-cyclization, cleavage, etc. This review describes the reactions of unsaturated derivatives of different heterocycles with various electrophilic agents (halogens, arylsulfanyl chlorides, mineral acids) resulting in annulation of an additional partially saturated heterocycle. The electrophilic reaction conditions, plausible mechanisms and the use of such transformations in organic synthesis are also discussed. The review mainly focuses on research published since 2002 in order to establish the current state of the art in this area. 1 Introduction2 Electrophilic Cyclization Pathways Involving a Nitrogen Nucleophilic Center3 Electrophilic Cyclization Pathways Involving a Chalcogen Nucleophilic Center3.1 Sulfur Centers3.2 Oxygen Centers3.3 Selenium Centers4 Strategies and Mechanisms5 Conclusion

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6

Caron, Maurice, Takeshi Kawamata, Luc Ruest, Pierre Soucy, and Pierre Deslongchamps. "The addition of electrophiles on ester enolates containing an oxygen in the β-position. A stereoelectronically controlled reaction." Canadian Journal of Chemistry 64, no. 9 (September 1, 1986): 1781–87. http://dx.doi.org/10.1139/v86-293.

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The enolate anion derived from spiro ketal methyl esters (1, 3, and 4) reacts with various electrophiles (PhSeBr, Ch3I, O2, I2, (CH3S)2, and (PhS)2) to yield as the major product, the isomer resulting from an equatorial approach of the electrophilic reagent. This stereochemically controlled reaction is discussed in terms of stereoelectronic effects that increase the electron density of the α face of the enolate anion.

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7

Dust, Julian M., and Erwin Buncel. "Reactions of the super-electrophile, 2-(2′,4′-dinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide, with methoxide and tert-butoxide: basicity and steric hindrance as factors in σ-complex formation versus nucleophilic displacement." Canadian Journal of Chemistry 69, no. 6 (June 1, 1991): 978–86. http://dx.doi.org/10.1139/v91-143.

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The course of the reactions of methoxide and tert-butoxide with 2-(2′,4′-dinitrophenyl)-4,6-dinitrobenzotriazole 1-oxide (4) clearly shows that the C-7 electrophilic site is significantly more reactive than the C-1′ site of the substrate. The reaction pathways of these alkoxides, which differ in basicity (as a measure of nucleophilicity) and steric bulk, were followed by 400 MHz 1H nuclear magnetic resonance spectroscopy. While both alkoxides lead to immediate formation of the respective C-7 anionic σ-adducts, a greater percentage of C-7 adduct formation occurs with methoxide as attacking nucleophile. Reaction with excess alkoxide results in attack at C-1′ being observed, as well. This leads to formation of metastable C-1′ σ-adducts, whose rapid decomposition results in formation of 2,4-dinitrophenyl ethers and the dinitrobenzotriazole 1-oxyanion in an overall nucleophilic displacement reaction. Under these excess conditions, methoxide also causes a faster rate of displacement than does tert-butoxide as nucleophile. These results are discussed on the basis of the basicity of the nucleophiles, the relative electrophilicity of the positions in the substrate (C-7 versus C-1′), the steric hindrance involved in attack and in the resultant C-7 and C-1′ complexes, and in terms of an activation energy/reaction coordinate profile comparing the pathways for attack at the two electrophilic sites. Key words: anionic σ-complexes, super-electrophiles, aromatic nucleophilic substitution (SN Ar).

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8

Doyle, Michael P. "Electrophilic metal carbenes as reaction intermediates in catalytic reactions." Accounts of Chemical Research 19, no. 11 (November 1986): 348–56. http://dx.doi.org/10.1021/ar00131a004.

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9

Kikuchi, Osamu. "Reaction potential map analysis of electrophilic aromatic substitution reactions." Journal of Molecular Structure: THEOCHEM 138, no. 1-2 (June 1986): 121–29. http://dx.doi.org/10.1016/0166-1280(86)87015-4.

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10

Ceaser, E. K., D. R. Moellering, S. Shiva, A. Ramachandran, A. Landar, A. Venkartraman, J. Crawford, et al. "Mechanisms of signal transduction mediated by oxidized lipids: the role of the electrophile-responsive proteome." Biochemical Society Transactions 32, no. 1 (February 1, 2004): 151–55. http://dx.doi.org/10.1042/bst0320151.

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Cellular redox signalling is mediated by the post-translational modification of proteins by reactive oxygen/nitrogen species or the products derived from their reactions. In the case of oxidized lipids, several receptor-dependent and -independent mechanisms are now emerging. At low concentrations, adaptation to oxidative stress in the vasculature appears to be mediated by induction of antioxidant defences, including the synthesis of the intracellular antioxidant glutathione. At high concentrations apoptosis occurs through mechanisms that have yet to be defined in detail. Recent studies have revealed a mechanism through which electrophilic lipids, formed as the reaction products of oxidation, orchestrate these adaptive responses in the vasculature. Using a proteomics approach, we have identified a subset of proteins in cells that we term the electrophile-responsive proteome. Electrophilic modification of thiol groups in these proteins can initiate cell signalling events through the transcriptional activation of genes regulated by consensus sequences for the antioxidant response element found in their promoter regions. The insights gained from our understanding of the biology of these mechanisms will be discussed in the context of cardiovascular disease.

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11

Satoh, Takumi, and Stuart Lipton. "Recent advances in understanding NRF2 as a druggable target: development of pro-electrophilic and non-covalent NRF2 activators to overcome systemic side effects of electrophilic drugs like dimethyl fumarate." F1000Research 6 (December 14, 2017): 2138. http://dx.doi.org/10.12688/f1000research.12111.1.

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Dimethyl fumarate (DMF) is an electrophilic compound previously called BG-12 and marketed under the name Tecfidera®. It was approved in 2013 by the US Food and Drug Administration and the European Medicines Agency for the treatment of relapsing multiple sclerosis. One mechanism of action of DMF is stimulation of the nuclear factor erythroid 2-related factor 2 (NRF2) transcriptional pathway that induces anti-oxidant and anti-inflammatory phase II enzymes to prevent chronic neurodegeneration. However, electrophiles such as DMF also produce severe systemic side effects, in part due to non-specific S-alkylation of cysteine thiols and resulting depletion of glutathione. This mini-review presents the present status and future strategy for NRF2 activators designed to avoid these side effects. Two modes of chemical reaction leading to NRF2 activation are considered here. The first mode is S-alkylation (covalent reaction) of thiols in Kelch-like ECH-associated protein 1 (KEAP1), which interacts with NRF2. The second mechanism involves non-covalent pharmacological inhibition of protein-protein interactions, in particular domain-specific interaction between NRF2 and KEAP1 or other repressor proteins involved in this transcriptional pathway. There have been significant advances in drug development using both of these mechanisms that can potentially avoid the systemic side effects of electrophilic compounds. In the first case concerning covalent reaction with KEAP1, monomethyl fumarate and monoethyl fumarate appear to represent safer derivatives of DMF. In a second approach, pro-electrophilic drugs, such as carnosic acid from the herb Rosmarinus officinalis, can be used as a safe pro-drug of an electrophilic compound. Concerning non-covalent activation of NRF2, drugs are being developed that interfere with the direct interaction of KEAP1-NRF2 or inhibit BTB domain and CNC homolog 1 (BACH1), which is a transcriptional repressor of the promoter where NRF2 binds.

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12

LIU, MIN-HSIEN, KEN-FA CHENG, CHENG CHEN, and YAW-SUN HONG. "SOLVENT EFFECT ON ELECTROPHILIC AND RADICAL SUBSTITUTION OF TOLUENE MONONITRATION REACTIONS." Journal of Theoretical and Computational Chemistry 07, no. 05 (October 2008): 965–76. http://dx.doi.org/10.1142/s0219633608004222.

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Two kinds of nitrating reagents, a nitronium cation [Formula: see text] and a nitro radical (· NO 2), were used in the gaseous phase toluene mononitration reaction. The closed shell calculation for electrophilic substitution and open shell calculation for radical substitution were both performed in solventless, H 2 O -solvated, and CH 3 OH -solvated molecular reaction systems. In the series of electrophilic toluene nitration reactions, both ortho-nitro toluene (o-MNT) and para-nitro toluene (p-MNT) are more abundant products than meta-nitro toluene (m-MNT), no matter what solvent is used in the reaction system. The reaction energy barrier for obtaining each kind of mononitro toluene follows a stepwise decreasing trend when the reaction is carried out in the solventless, H 2 O -solvated, and CH 3 OH -solvated systems. In all radical toluene nitration reactions, solventless or solvated, m-MNT is the most abundant product. The energy barrier data also show that the nitration reaction is more feasible in a solvated than in a solventless system. H 2 O has a more obvious solvent effect than CH 3 OH in the · NO 2 radical substitution reaction, and the H 2 O -solvated system provides a lower activation energy reaction path.

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13

Ouled Aitouna, Abdelhak, Lahoucine Bahsis, Hicham Ben El Ayouchia, Ahmed Chekroun, Redouan Hammal, and Ahmed Benharref. "A DFT reinvestigation of chemo- and stereoselectivity epoxidation from α- and ɣ-trans himachalene with meta Chloroperoxybenzoic acid." Mediterranean Journal of Chemistry 9, no. 2 (September 19, 2019): 133–41. http://dx.doi.org/10.13171/mjc92190919645aoa/hbe.

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In this work the epoxidation reaction of the α- and ɣ-trans himachalene in the presence of meta chloroperoxybenzoic acid (m-CPBA) has been studied within the Density Functional Theory (DFT) method at the B3LYP/6-311G(d,p) level in dichloromethane as a solvent, in order to shed light on the chemo- and stereoselectivity in the course of the reaction. Analysis of the Conceptual Density Functional Theory (CDFT) reactivity indices indicate that the m-CPBA will behave as electrophilic while α- and ɣ-trans himachalene will behave as a nucleophile and the attacks observed experimentally are correctly predicted by the electrophilic Pk + and nucleophilic Pk - Parr functions. The two reactive paths associated with chemo and stereoselectivity approach modes of m-CPBA on C=C reactive sites in α and ɣ-trans himachalene have been analyzed. They showed that m-CPBA reacted as electrophile whereas α- and ɣ- trans himachalene as a nucleophile. The Monoepoxidation of α- and ɣ- trans himachalene leads to the formation of two stereoisomers, on the most substituted double bond "C=C», one of the two is a majority. The diepoxidation reaction of α- and ɣ- trans h

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14

Gravel, Denis, and Marc Labelle. "The γ-alkylation of cyclic β-ketoesters via their enamine derivatives." Canadian Journal of Chemistry 63, no. 7 (July 1, 1985): 1874–83. http://dx.doi.org/10.1139/v85-311.

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The γ-alkylation – functionalization of cyclic β-ketoesters via their enamine derivatives is discussed with particular emphasis on their preparation from β-ketoesters and their reaction with various electrophiles such as electrophilic olefins, halogenoïds, and allylic and benzylic halides. Although the amine ring size does not appear to affect reactivity to a great extent, the reaction is very sensitive to β-ketoester ring size, with six-membered rings giving the best results. In the latter case the alkylation–functionalization is general and specific to the γ-position and therefore provides an important complement to the dianion and related methodologies.

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15

Rocard, Lou, and Piétrick Hudhomme. "Recent Developments in the Suzuki–Miyaura Reaction Using Nitroarenes as Electrophilic Coupling Reagents." Catalysts 9, no. 3 (February 26, 2019): 213. http://dx.doi.org/10.3390/catal9030213.

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Palladium-catalyzed cross-coupling reactions are nowadays essential in organic synthesis for the construction of C–C, C–N, C–O, and other C-heteroatom bonds. The 2010 Nobel Prize in Chemistry to Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki was awarded for the discovery of these reactions. These great advances for organic chemists stimulated intense research efforts worldwide dedicated to studying these reactions. Among them, the Suzuki–Miyaura coupling (SMC) reaction, which usually involves an organoboron reagent and an organic halide or triflate in the presence of a base and a palladium catalyst, has become, in the last few decades, one of the most popular tools for the creation of C–C bonds. In this review, we present recent progress concerning the SMC reaction with the original use of nitroarenes as electrophilic coupling partners reacting with the organoboron reagent.

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16

Fan, Xuesen, Xueyuan Hu, Xinying Zhang, and Jianji Wang. "Ionic Liquid Promoted Knoevenagel and Michael Reactions." Australian Journal of Chemistry 57, no. 11 (2004): 1067. http://dx.doi.org/10.1071/ch04060.

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The utilization of the ionic liquid [bmim][BF4] as both reaction medium and promoter for the Knoevenagel condensation and Michael addition reactions is described in this paper. Through these reactions, several useful electrophilic alkenes and chromene derivatives are obtained in high yields. The advantages of these two novel procedures include their environmentally benign nature, atom economy, simple operation process, and mild reaction conditions.

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17

Choi, Han Young, Ekaruth Srisook, Kun Sam Jang, and Dae Yoon Chi. "Electrophilic Aromatic Addition Reaction: Electrophilic Attack at an Aromatic H Substituent Position." Journal of Organic Chemistry 70, no. 4 (February 2005): 1222–26. http://dx.doi.org/10.1021/jo048297x.

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18

Rousseaux, Sophie, and L. Mills. "Electrophilic Metal Homoenolates and Their Application in the Synthesis of Cyclopropylamines." Synlett 29, no. 06 (February 19, 2018): 683–88. http://dx.doi.org/10.1055/s-0036-1591536.

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Since their discovery, metal homoenolates have been widely explored as carbon-based nucleophiles for the β-functionalization of carbonyl derivatives. Only recently has it been reported that metal homoenolates can react as carbonyl electrophiles. In this context, we have recently discovered that cyclopropylamines can be prepared from cyclopropanols via zinc homoenolate intermediates. This Synpacts article will present an overview of the reactivity of homoenolates and our strategy to employ these intermediates for the synthesis of cyclopropylamines. Key mechanistic observations and their influence on reaction optimization will also be discussed.1 Introduction2 Homoenolates as Nucleophiles—Selected Reactivity3 Homoenolates as Electrophilic Reagents4 Conclusion

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19

Cai, Yuanting, Yuhui Hua, Zhengyu Lu, Qing Lan, Zuzhang Lin, Jiawei Fei, Zhixin Chen, Hong Zhang, and Haiping Xia. "Electrophilic aromatic substitution reactions of compounds with Craig-Möbius aromaticity." Proceedings of the National Academy of Sciences 118, no. 39 (September 20, 2021): e2102310118. http://dx.doi.org/10.1073/pnas.2102310118.

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Electrophilic aromatic substitution (EAS) reactions are widely regarded as characteristic reactions of aromatic species, but no comparable reaction has been reported for molecules with Craig-Möbius aromaticity. Here, we demonstrate successful EAS reactions of Craig-Möbius aromatics, osmapentalenes, and fused osmapentalenes. The highly reactive nature of osmapentalene makes it susceptible to electrophilic attack by halogens, thus osmapentalene, osmafuran-fused osmapentalene, and osmabenzene-fused osmapentalene can undergo typical EAS reactions. In addition, the selective formation of a series of halogen substituted metalla-aromatics via EAS reactions has revealed an unprecedented approach to otherwise elusive compounds such as the unsaturated cyclic chlorirenium ions. Density functional theory calculations were conducted to study the electronic effect on the regioselectivity of the EAS reactions.

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20

Bagheri, Mojtaba, Najmedin Azizi, and Mohammad R. Saidi. "An intriguing effect of lithium perchlorate dispersed on silica gel in the bromination of aromatic compounds by N-bromosuccinimide." Canadian Journal of Chemistry 83, no. 2 (February 1, 2005): 146–49. http://dx.doi.org/10.1139/v05-001.

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A convenient and efficient procedure for electrophilic aromatic bromination has been developed by mixing of N-bromosuccinimide and an aromatic compound at room temperature on the surface of silica gel mixed with solid anhydrous LiClO4. All of the substrates examined underwent clean electrophilic aromatic bromination in reaction times of a few minutes to afford the corresponding bromoarenes under neutral conditions in excellent yield. In the case of thiophenol, no substitution reaction occurred, and the corresponding disulfide was obtained in excellent yield.Key words: LP-SiO2, NBS, arenes, electrophilic bromination, regioselectivity.

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21

Sheng, Xia, Kaijun Chen, Chengjin Shi, and Dayun Huang. "Recent Advances in Reactions of Propargylamines." Synthesis 52, no. 01 (October 8, 2019): 1–20. http://dx.doi.org/10.1055/s-0039-1690684.

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Propargylamines are extremely versatile and common building blocks in the field of chemistry. This review highlights the recent advances made in the reactions of propargylamines between 2009 and 2019. The reaction types are classified into six categories based on the trigger mechanisms: (1) amino moieties as leaving groups, (2) hydrogenation, (3) rearrangement, (4) nucleophilic amines, (5) nucleophilic carbons, and (6) electrophilic alkynes. We hope that this review will promote future research in this area.1 Introduction2 Amino Moieties as Leaving Groups3 Hydrogenation4 Rearrangement5 Nucleophilic Amines6 Nucleophilic Carbons 7 Electrophilic Alkynes8 Conclusions

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22

Hartmann, Horst, Jürgen Liebscher, and Peter Czerney. "Reaction of N-acylthioureas with electrophilic reagents." Tetrahedron 41, no. 22 (January 1985): 5371–76. http://dx.doi.org/10.1016/s0040-4020(01)96792-4.

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23

Jang, Keun Sam, Hee Young Shin, and Dae Yoon Chi. "Electrophilic aromatic addition reaction (AdEAr) to anthracene." Tetrahedron 64, no. 24 (June 2008): 5666–71. http://dx.doi.org/10.1016/j.tet.2008.04.032.

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24

Li, Guigen, Han-Xun Wei, Sun Hee Kim, and Michael D. Carducci. "A Novel Electrophilic Diamination Reaction of Alkenes." Angewandte Chemie International Edition 40, no. 22 (November 16, 2001): 4277–80. http://dx.doi.org/10.1002/1521-3773(20011119)40:22<4277::aid-anie4277>3.0.co;2-i.

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25

Li, Guigen, Han-Xun Wei, Sun Hee Kim, and Michael D. Carducci. "A Novel Electrophilic Diamination Reaction of Alkenes." Angewandte Chemie 113, no. 22 (November 19, 2001): 4407–10. http://dx.doi.org/10.1002/1521-3757(20011119)113:22<4407::aid-ange4407>3.0.co;2-u.

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26

Kravchenko, A. N., A. S. Sigachev, G. A. Gazieva, E. Yu Maksareva, N. S. Trunova, K. A. Chegaev, K. A. Lyssenko, et al. "Reaction of N-alkylglycolurils with electrophilic reagents." Chemistry of Heterocyclic Compounds 42, no. 3 (March 2006): 365–76. http://dx.doi.org/10.1007/s10593-006-0094-2.

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27

Arnett, Edward M., Kalyani Amarnath, and Sampath Venimadhavan. "Heats of reaction for nucleophilic and electrophilic displacement reactions in solution." Journal of Organic Chemistry 55, no. 11 (May 1990): 3593–96. http://dx.doi.org/10.1021/jo00298a040.

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28

Reddy, A. Srinivas, and Kenneth K. Laali. "Reaction of allene esters with Selectfluor/TMSX (X = I, Br, Cl) and Selectfluor/NH4SCN: Competing oxidative/electrophilic dihalogenation and nucleophilic/conjugate addition." Beilstein Journal of Organic Chemistry 11 (September 16, 2015): 1641–48. http://dx.doi.org/10.3762/bjoc.11.180.

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Reaction of benzyl and ethyl allenoates with TMSX (X = I, Br, Cl) and with NH4SCN were investigated in MeCN, DMF, and in imidazolium ionic liquids [BMIM][NTf2] and [BMIM][PF6] as solvent, in the presence and absence of Selectfluor. Comparative product analysis studies demonstrate that the ability of Selectflour to promote oxidative/electrophilic dihalogenation/dithiocyanation with TMSX/NH4SCN (as observed previously for 1-arylallenes) is diminished in allenoates, most significantly in reactions with TMSCl, and essentially disappearing in reactions with NH4SCN, in favor of nucleophilic/conjugate addition. The study underscores the contrasting reactivity patterns in 1-arylallenes and allenoates toward electrophilic and nucleophilic additions in halofunctionalization with TMSX/Selectfluor and thiocyanation reactions with NH4SCN/Selectfluor. These competing pathways are influenced by the nature of the anion, allene structure, and the choice of solvent.

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29

Kranke, Birgit, and Horst Kunz. "Stereoselective synthesis of chiral piperidine derivatives employing arabinopyranosylamine as the carbohydrate auxiliary." Canadian Journal of Chemistry 84, no. 4 (April 1, 2006): 625–41. http://dx.doi.org/10.1139/v06-060.

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Stereoselective synthesis of 2-substituted dehydropiperidinones and their further transformation to variously disubstituted piperidine derivatives was achieved employing D-arabinopyranosylamine as the stereodifferentiating carbohydrate auxiliary. A domino MannichMichael reaction of 1-methoxy-3-(trimethylsiloxy)butadiene (Danishefsky's diene) with O-pivaloylated arbinosylaldimines furnished N-arabinosyl dehydropiperidinones in high diastereoselectivity. Subsequent conjugate cuprate addition gave 2,6-cis-substituted piperidinones, while enolate alkylation furnished 2,3-trans-substituted dehydropiperidinones. Electrophilic substitution at the enamine structure afforded 5-nitro- and 5-halogen dehydropiperidinones of which the latter were applied in palladium-catalyzed coupling reactions. The absolute configuration of the obtained products was proven by NMR and X-ray structure analysis as well as by syntheses of the alkaloids (+)-coniine and (+)-dihydropinidine.Key words: piperidine alkaloids, carbohydrate auxiliary, domino MannichMichael reaction, conjugate cuprate and hydride addition, electrophilic substitution of enamines.

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30

Kysil, Andrii, Angelina Biitseva, Tetyana Yegorova, Igor Levkov, and Zoia Voitenko. "Reaction of 1-aminoisoindole with methyl 4-chloro-3-oxobutanoate." French-Ukrainian Journal of Chemistry 6, no. 2 (2018): 32–37. http://dx.doi.org/10.17721/fujcv6i2p32-37.

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Condensation of bifunctional 1-aminoisoindole with bis-electrophilic methyl 4-chloro-3-oxobutanoate undergoes regioselectively to afford 2-(chloromethyl)-2-hydroxy-2,6-dihydropyrimido[2,1-a]isoindol-4(3H)-one. The structure of the reaction product was unambiguously established by HMQC and HMBC heteronuclear correlations. The functionalization of the synthesized compound by reactions with a series of aliphatic amines was carried out.

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31

Suárez-Pantiga, Samuel, and José M. González. "Electrophilic activation of unsaturated systems: Applications to selective organic synthesis." Pure and Applied Chemistry 85, no. 4 (March 13, 2013): 721–39. http://dx.doi.org/10.1351/pac-con-12-10-24.

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Selected examples from previous work on iodonium-triggered approaches for the functionalization of unsaturated systems, which summarize innovative transformations, are presented. This section is mostly focused on C–C bond-forming processes from alkynes that are directly bonded to relevant heteroatoms, such as iodine, silicon, or sulfur. Besides, recent advances related to iodonium-promoted C–H functionalization reactions are briefly outlined. A second section shows representative examples of our current research activity on electrophilic reactions aimed at the activation of unsaturated systems, which now are built upon the potential offered by the so-called carbophilic catalysis. More specifically, a new catalytic cyclopentannulation sequence from N-tosylimines and propargyl tosylates and novel C–H functionalization processes from related tosylates are studied. Likewise, representative examples for the intermolecular Au(I)-catalyzed [2 + 2] cycloaddition reaction of sulfonylallenamides with activated alkenes are given, including the first enantioselective reaction of this type, which is also among the first examples of an intermolecular asymmetric gold-catalyzed reaction. The discussion of the reported iodonium and gold chemistry emphasizes a search for new intermolecular processes, although intramolecular reactions are also pursued and developed.

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32

Ríos-Gutiérrez, Mar, Andrea Darù, Tomás Tejero, Luis R. Domingo, and Pedro Merino. "A molecular electron density theory study of the [3 + 2] cycloaddition reaction of nitrones with ketenes." Organic & Biomolecular Chemistry 15, no. 7 (2017): 1618–27. http://dx.doi.org/10.1039/c6ob02768g.

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The zw-type 32CA reactions of nitrones with ketenes are controlled by the nucleophilic character of the nitrone and the electrophilic character of the ketene. They are chemo- and regio-selective and the use of electrophilic ketenes changes the mechanism from one-step to two-step.

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33

Tokarz-Sobieraj, Renata, Robert Grybos, Małgorzata Witko, and Klaus Hermann. "Oxygen Sites at Molybdena and Vanadia Surfaces: Energetics of the Re-Oxidation Process." Collection of Czechoslovak Chemical Communications 69, no. 1 (2004): 121–40. http://dx.doi.org/10.1135/cccc20040121.

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In oxidation reactions proceeding in accordance with the Mars-van Krevelen mechanism lattice oxygen plays the role of an oxidizing agent. Surface vacancies created by incorporation of lattice oxygen into reacting molecules are filled in a subsequent step by gaseous oxygen or, if not enough oxygen is present in the reaction environment, by oxygen diffusion from the bulk. During this process, a very active, electrophilic surface oxygen species may be formed. In effect, total combustion takes place decreasing the selectivity for partial oxidation products. The thermodynamic aspect of this effect (neglecting reaction barriers) is demonstrated for molybdenum trioxide and vanadium pentoxide. On the catalytically most interesting surfaces, MoO3(010) and V2O5(010), three structurally different types of oxygen sites are present which exhibit different properties with respect to vacancy creation and annihilation. Re-oxidation of the catalyst by gaseous oxygen leads to oxygen molecules adsorbed in vacancies, preferably in an orientation parallel to the surface. Adsorption of the oxygen molecule in the vacancy leads to its activation followed by easy release of a neutral oxygen atom, which can be identified as the electrophilic species responsible for total combustion.

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34

Lindner, Christoph, Raman Tandon, Boris Maryasin, Evgeny Larionov, and Hendrik Zipse. "Cation affinity numbers of Lewis bases." Beilstein Journal of Organic Chemistry 8 (August 31, 2012): 1406–42. http://dx.doi.org/10.3762/bjoc.8.163.

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Using selected theoretical methods the affinity of a large range of Lewis bases towards model cations has been quantified. The range of model cations includes the methyl cation as the smallest carbon-centered electrophile, the benzhydryl and trityl cations as models for electrophilic substrates encountered in Lewis base-catalyzed synthetic procedures, and the acetyl cation as a substrate model for acyl-transfer reactions. Affinities towards these cationic electrophiles are complemented by data for Lewis-base addition to Michael acceptors as prototypical neutral electrophiles.

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35

Wang, Yuqing, Gaigai Wang, Anatoly A. Peshkov, Ruwei Yao, Muhammad Hasan, Manzoor Zaman, Chao Liu, Stepan Kashtanov, Olga P. Pereshivko, and Vsevolod A. Peshkov. "Controlling the stereochemistry in 2-oxo-aldehyde-derived Ugi adducts through the cinchona alkaloid-promoted electrophilic fluorination." Beilstein Journal of Organic Chemistry 16 (August 11, 2020): 1963–73. http://dx.doi.org/10.3762/bjoc.16.163.

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In this report, we introduce a new strategy for controlling the stereochemistry in Ugi adducts. Instead of controlling stereochemistry directly during the Ugi reaction we have attempted to stereodefine the chiral center at the peptidyl position through the post-Ugi functionalization. In order to achieve this, we chose to study 2-oxo-aldehyde-derived Ugi adducts many of which partially or fully exist in the enol form that lacks the aforementioned chiral center. This in turn led to their increased nucleophilicity as compared to the standard Ugi adducts. As such, the stereocenter at the peptidyl position could be installed and stereodefined through the reaction with a suitable electrophile. Towards this end, we were able to deploy an asymmetric cinchona alkaloid-promoted electrophilic fluorination producing enantioenriched post-Ugi adducts fluorinated at the peptidyl position.

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36

Walter, Christopher, Natalie Fallows, and Tanay Kesharwani. "Copper-Catalyzed Electrophilic Chlorocyclization Reaction Using Sodium Chloride as the Source of Electrophilic Chlorine." ACS Omega 4, no. 4 (April 9, 2019): 6538–45. http://dx.doi.org/10.1021/acsomega.9b00300.

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37

Kim, Young Heui, Tae Ho Kim, Na Young Kim, Eun Sook Cho, Bun Yeoul Lee, Dong Mok Shin, and Young Keun Chung. "Activation of Enamido Zirconium Complexes for Ethylene Polymerization: Electrophilic Addition versus Electrophilic Abstraction Reaction." Organometallics 22, no. 7 (March 2003): 1503–11. http://dx.doi.org/10.1021/om020949p.

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38

Díaz-Urrutia, Christian, and Timo Ott. "Response to Comment on “Activation of methane to CH3+: A selective industrial route to methanesulfonic acid”." Science 369, no. 6504 (August 6, 2020): eaax9966. http://dx.doi.org/10.1126/science.aax9966.

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Roytman and Singleton argue that our proposed electrophilic mechanism for the sulfonation of methane in superacid conditions is “not plausible.” We clarify certain terms that might have caused misinterpretation of our proposed mechanism and supplement the discussion. We reaffirm that an electrophilic mechanism may be operative under our reaction conditions.

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39

Tan, Jiajing, Binbin Liu, and Shuaisong Su. "Aryne triggered dearomatization reaction of isoquinolines and quinolines with chloroform." Organic Chemistry Frontiers 5, no. 21 (2018): 3093–97. http://dx.doi.org/10.1039/c8qo00838h.

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40

Brownridge, Scott, Jack Passmore, and Xiaoping Sun. "The electrophilic substitution reaction of the dithionitronium cation [SNS]+ with benzene." Canadian Journal of Chemistry 76, no. 8 (August 1, 1998): 1220–31. http://dx.doi.org/10.1139/v98-148.

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The compound [SNS]+([SNS][AsF6]) reacts with benzene in liquid sulfur dioxide to give orange-, blue-, and then purple-colored solutions. The assignment of the orange color to a molecule-ion charge-transfer complex [C6H6·SNS]+ is supported by the linear dependence of the ionization potential of the arenes (C6H6, C6HMe5, C6H5But, C6HMe5) and the energy of the charge-transfer absorption of freshly prepared arene-[SNS][AsF6] mixtures in liquid SO2 solution. Variable-temperature multinuclear NMR studies of the reactions of [SNS][AsF6] and [SNS][Sb2F11] with benzene are consistent with the blue color being due to a sulfur protonated substitution product [C6H5(S2N)H]+, providing the first example of a CH electrophilic substitution reaction of SNS+. The geometries calculated at the RHF/6-31G' level for [C6H5(SNS)H]+, the isomeric [C6H5NSSH]+, and [C6H5N(S)SH]+, together with NMR data, support [C6H5(SNS)H]+(i.e., suggest S, not N, is attached to the ring) as the structure of the cation. The electrophilic aromatic substitution reaction of [SNS]+ and benzene is also supported by NMR studies of [SNS][AsF6] and other arenes (e.g., C6HMe5) in SO2 solution. The UV-visible spectrum of [SNS]+ ([SNS][AsF6]) in liquid SO2 is reported, and the absorption ( lamda = 406 nm, epsilon = 80) responsible for the yellow color is assigned to the [SNS]+ HOMO-LUMO transition. Evidence is also presented for the formation of a molecule-ion charge-transfer complex between 5-methyl-1,3,2,4-dithiadiazolium and hexamethylbenzene in liquid SO2, the first dithiadiazolium charge-transfer complex.Key words: UV-visible, charge transfer, dithionitronium, benzene, electrophilic substitution.

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41

Gualandi, Andrea, Luca Mengozzi, and Pier Cozzi. "Stereoselective SN1-Type Reaction of Enols and Enolates." Synthesis 49, no. 15 (June 13, 2017): 3433–43. http://dx.doi.org/10.1055/s-0036-1588871.

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Stereoselective alkylation of enolates represents a valuable and important procedure for accessing carbon–carbon-bond frameworks in natural and nonnatural product synthesis. Usually, activated electrophilic partners that react through an SN2 mechanism are employed. To overcome the limitations due to reduced reactivity and steric hindrance, SN1-type reactions can be considered a valid and practical alternative. Accessible enolates can be used in stereoselective (diastereo- or enantioselective) reactions with electrophilic carbenium ions, either used as stable reagents or generated in situ from suitable precursors. The results achieved in this active field are summarized in this review.1 Introduction2 Alcohols in SN1-Type Reactions with Enolates2.1 Enantioselective Reactions with Metal Complexes2.2 Organocatalytic Enantioselective Reactions3 Alcohols and Alcohol Derivatives in SN1-Type Reactions with Enolates: Enantioselective Reactions with Metal Enolates4 Isolated Carbenium Ions in SN1-Type Reactions with Enolates: Enantioselective Reactions with Metal Enolates5 Miscellaneous6 Conclusion

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42

Appelbaum, L., D. Danovich, G. Lazanes, M. Michman, and M. Oron. "An electrochemical aromatic chlorination, comparison with electrophilic reaction." Journal of Electroanalytical Chemistry 499, no. 1 (February 2001): 39–47. http://dx.doi.org/10.1016/s0022-0728(00)00465-4.

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43

Liu, Zhongquan, Bo Zhou, Zhongli Liu, and Longmin Wu. "Electrophilic reaction of nitric oxide with Wittig reagents." Tetrahedron Letters 46, no. 7 (February 2005): 1095–97. http://dx.doi.org/10.1016/j.tetlet.2004.12.087.

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44

COOMBES, R. G. "ChemInform Abstract: Electrophilic Aromatic Substitution (Organic Reaction Mechanisms)." ChemInform 25, no. 18 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199418284.

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45

Yamada, Kohei, Yukiko Karuo, Yuichi Tsukada, and Munetaka Kunishima. "Mild Amide-Cleavage Reaction Mediated by Electrophilic Benzylation." Chemistry - A European Journal 22, no. 39 (August 16, 2016): 14042–47. http://dx.doi.org/10.1002/chem.201603120.

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46

Grushin, Vladimir V., William J. Marshall, and David L. Thorn. "Electrophilic Stannylation of Arenes: A New SEAr Reaction." Advanced Synthesis & Catalysis 343, no. 5 (July 2001): 433–38. http://dx.doi.org/10.1002/1615-4169(200107)343:5<433::aid-adsc433>3.0.co;2-3.

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47

MOODIE, R. B. "ChemInform Abstract: Electrophilic Aromatic Substitution (Organic Reaction Mechanisms)." ChemInform 22, no. 45 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199145326.

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48

Pelkey, Erin T., and Gordon W. Gribble. "Novel electrophilic ipso acylation - detosylation reaction of pyrroles." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1338–42. http://dx.doi.org/10.1139/v06-075.

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A pyrrole and two pyrroloindoles that are substituted with a p-toluenesulfonyl group undergo an ipso acylation – detosylation reaction with acid chlorides and aluminum chloride to afford the corresponding acyl-substituted pyrroles and pyrroloindoles.Key words: pyrrole, pyrroloindole, ipso acylation, detosylation, Friedel–Crafts reaction.

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49

Liepins, Vilnis, and Jan-E. Bäckvall. "Silylcupration of styrenes followed by electrophilic trapping reaction." Chemical Communications, no. 3 (2001): 265–66. http://dx.doi.org/10.1039/b009148k.

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50

Nikonov, G. N., A. S. Balueva, A. A. Karasik, I. A. Litvinov, O. A. Erastov, B. A. Arbuzov, and V. A. Nauraov. "Reaction of ammonium 1,3,2,5-dioxaborataphosphorinanes with electrophilic reagents." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 37, no. 1 (January 1988): 143–47. http://dx.doi.org/10.1007/bf00962675.

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