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Journal articles on the topic 'Activation iminium'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 May 2024

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1

Tontsch, Christian J., Holger Gerster, and Gerhard Maas. "Iminium-functionalized 1,2,3-triazoles by [3+2] cycloaddition reactions of internal acetylenic iminium triflates with organoazides." Zeitschrift für Naturforschung B 74, no. 7-8 (2019): 585–602. http://dx.doi.org/10.1515/znb-2019-0079.

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AbstractPropyne iminium triflates 1–6 react as dipolarophiles in thermal [3 + 2]-cycloadditions with sufficiently electron rich organoazides to form 1,4,5-trisubstituted 1,2,3-triazoles with iminium functionalization. The reactions require rather strong thermal activation, but can be accelerated by microwave irradiation. The regioselectivity of the cycloaddition at the internal acetylenic bond of 3-cyclopropylpropyne and 3-arylpropyne iminium ions (1–3 and 4, respectively) is very high, but is lowered in the presence of sterically demanding substituents at the opposite end of the iminium-subst

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2

Riaño, Iker, Uxue Uria, Luisa Carrillo, Efraim Reyes, and Jose L. Vicario. "4-Alkenyl-5H-1,2,3-oxathiazole 2,2-dioxides in catalytic and enantioselective [4 + 2] cycloaddition through iminium activation. Straightforward access to the trans-decaline framework and to densely functionalized cyclohexanes." Organic Chemistry Frontiers 2, no. 3 (2015): 206–10. http://dx.doi.org/10.1039/c4qo00316k.

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3

Wagh, Sandip, and Ganesh Dhage. "Primary-Secondary Diamine Catalyzed Enantioselective Synthesis of Substituted Cyclohex-2-enones by Cascade Michael–Aldol–Dehydration of Ketones with Chalcones." Synlett 28, no. 11 (2017): 1353–57. http://dx.doi.org/10.1055/s-0036-1588976.

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A simple primary-secondary diamine organocatalyst catalyzes the cascade Michael–aldol–dehydration of chalcones and unmodified ketones to produce substituted cyclohex-2-enones under mild conditions with good yields and high enantio- and/or diastereoselectivities. The success of the catalyst system is possibly due to simultaneous activation of the electrophilic chalcone by iminium formation and the nucleophilic ketone by enamine formation with an overall intramolecular iminium–di-enamine mechanism.

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4

Holland, M. C., J. B. Metternich, C. Mück-Lichtenfeld та R. Gilmour. "Cation–π interactions in iminium ion activation: correlating quadrupole moment & enantioselectivity". Chemical Communications 51, № 25 (2015): 5322–25. http://dx.doi.org/10.1039/c4cc08520e.

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5

Vermeeren, Pascal, Trevor A. Hamlin, Israel Fernández, and F. Matthias Bickelhaupt. "Origin of rate enhancement and asynchronicity in iminium catalyzed Diels–Alder reactions." Chemical Science 11, no. 31 (2020): 8105–12. http://dx.doi.org/10.1039/d0sc02901g.

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6

Lakhdar, Sami, Roland Appel, and Herbert Mayr. "How Does Electrostatic Activation Control Iminium-Catalyzed Cyclopropanations?" Angewandte Chemie International Edition 48, no. 27 (2009): 5034–37. http://dx.doi.org/10.1002/anie.200900933.

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7

Dou, Xiaowei, Weijun Yao, Chunhui Jiang, and Yixin Lu. "Enantioselective N-alkylation of isatins and synthesis of chiral N-alkylated indoles." Chem. Commun. 50, no. 77 (2014): 11354–57. http://dx.doi.org/10.1039/c4cc04586f.

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Asymmetric N-alkylations of isatins with enals were shown to be feasible via a prolinol-catalyzed iminium activation, and N-alkylated isatins and indoles were obtained in good yields and with excellent enantioselectivity.

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8

Kano, Taichi, Yusuke Aota, Daisuke Asakawa, and Keiji Maruoka. "Brønsted acid-catalyzed Mannich reaction through dual activation of aldehydes and N-Boc-imines." Chemical Communications 51, no. 92 (2015): 16472–74. http://dx.doi.org/10.1039/c5cc07290e.

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In the presence of a Brønsted acid catalyst, both aldehydes and N-Boc-aminals were converted to enecarbamates and N-Boc-iminium salts as activated nucleophiles and electrophiles, respectively, giving unprecedented Mannich adducts.

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9

Domingo, Luis R., Mar Ríos-Gutiérrez, and María José Aurell. "Unveiling the Ionic Diels–Alder Reactions within the Molecular Electron Density Theory." Molecules 26, no. 12 (2021): 3638. http://dx.doi.org/10.3390/molecules26123638.

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The ionic Diels–Alder (I-DA) reactions of a series of six iminium cations with cyclopentadiene have been studied within the Molecular Electron Density Theory (MEDT). The superelectrophilic character of iminium cations, ω > 8.20 eV, accounts for the high reactivity of these species participating in I-DA reactions. The activation energies are found to be between 13 and 20 kcal·mol−1 lower in energy than those associated with the corresponding Diels–Alder (DA) reactions of neutral imines. These reactions are low endo selective as a consequence of the cationic character of the TSs, but highly r

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10

Appel, Roland, Saloua Chelli, Takahiro Tokuyasu, Konstantin Troshin, and Herbert Mayr. "Electrophilicities of Benzaldehyde-Derived Iminium Ions: Quantification of the Electrophilic Activation of Aldehydes by Iminium Formation." Journal of the American Chemical Society 135, no. 17 (2013): 6579–87. http://dx.doi.org/10.1021/ja401106x.

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11

Vicario, Jose L., Efraim Reyes, Dolores Badia, and Luisa Carrillo. "ChemInform Abstract: Iminium Activation in Catalytic Enantioselective Conjugate Additions." ChemInform 42, no. 50 (2011): no. http://dx.doi.org/10.1002/chin.201150247.

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12

Zhu, Haipan, Peile Du, Jianjun Li, et al. "Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals." Beilstein Journal of Organic Chemistry 12 (June 29, 2016): 1340–47. http://dx.doi.org/10.3762/bjoc.12.127.

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A cooperative catalytic strategy of chiral iminium catalysis by regioselective activation of the C=C bond in enals and a transition metal promoting to open the 2-vinylcyclopropanes for highly regio- and enantioselective [3 + 2] cycloaddition reaction of 2-vinylcyclopropanes with α,β-unsaturated aldehydes has been developed.

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13

Sparr, Christof, and Ryan Gilmour. "Cyclopropyl Iminium Activation: Reactivity Umpolung in Enantioselective Organocatalytic Reaction Design." Angewandte Chemie International Edition 50, no. 36 (2011): 8391–95. http://dx.doi.org/10.1002/anie.201103360.

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14

Sparr, Christof, and Ryan Gilmour. "Cyclopropyl Iminium Activation: Reactivity Umpolung in Enantioselective Organocatalytic Reaction Design." Angewandte Chemie 123, no. 36 (2011): 8541–45. http://dx.doi.org/10.1002/ange.201103360.

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15

Zhang, Xiao-Ru, Su-Lan Zhou, Yi Yuan, Wei Du та Ying-Chun Chen. "Chemo- and Regioselective Asymmetric Friedel–Crafts Reaction of Furans and Thiophenes with α,β-Unsaturated Aldehydes through Dual Activation". Synlett 28, № 14 (2017): 1771–74. http://dx.doi.org/10.1055/s-0036-1588831.

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A highly chemo- and regioselective Friedel–Crafts alkylation reaction of furans and thiophenes has been developed, which relies on the activation from the remote conjugated Mukaiyama silyl enol ether motif. Excellent enantioslectivity is generally obtained in reactions with α,β-unsaturated aldehydes under the well-established iminium ion catalysis of a chiral secondary amine.

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16

Zanardi, Franca, Claudio Curti, Andrea Sartori та Lucia Battistini. "Exploring the Remote Reactivity of π-Extended Carbonyl Compounds: The Vinylogous Alkylidene Malononitrile Activation Strategy". Synlett 29, № 03 (2017): 266–81. http://dx.doi.org/10.1055/s-0036-1589125.

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The installation of malononitrile into π-extended carbonyl compounds gives rise to vinylogous alkylidene malononitriles (also known as π-extended dicyanovinylidenes), the direct functionalization of which at remote C(sp3) pronucleophilic sites becomes possible and viable. Starting from easily accessible representative polyunsaturated malononitriles, mild conditions were found to directly couple them to complementary enal acceptors. In all cases, the malononitrile handle proved an indispensable (and optionally traceless) activating ingredient for the vinylogous reactions to proceed efficiently

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17

Flores-Morales, Virginia, Eduardo D. Ayala-Medrano, José García-Elías, Margarita L. Martínez-Fierro, Edgar Marquez, and José Mora. "Understanding the Lack of Reactivity of 2,4-Dihydroxybenzaldehyde Towards the Biginelli Adduct Using Density Functional Theory Molecular Modeling." Processes 7, no. 8 (2019): 521. http://dx.doi.org/10.3390/pr7080521.

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The Biginelli reaction is a multicomponent reaction for obtaining dihydropyrimidinthiones quickly, with multiple substitution patterns. The reaction mechanism remains unclear. Three possible pathways proposed for the reaction are the iminium route, an enamine intermediate, and the Knoevenagel pathway. However, when thiourea was used, no theoretical calculations were reported. Thus, based on the literature, the iminium pathway was used to obtain evidence explaining the lack of reactivity of 2,4-dihydroxybenzaldehyde towards the Biginelli adduct, compared with 4-hydroxybenzaldehyde. This computa

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18

Maas, Gerhard, Bianca Seitz, Thomas Schneider, Nikola Majstorovic, and Maximilian Fleischmann. "Reactions of 1-Trifluoromethylprop-2-yne 1-Iminium Salts with Nitroanilines: Synthesis of 4-Trifluoromethylnitroquinolines and 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles." Synthesis 54, no. 08 (2021): 2057–69. http://dx.doi.org/10.1055/a-1685-2279.

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AbstractA variety of 4-trifluoromethylquinolines bearing an aryl (or cyclopropyl, tert-butyl, trimethylsilyl) group at C-2 and a nitro group at ring position 6, 7 or 8 have been prepared in good to high yields from 3-substituted 1-(trifluoromethyl)prop-2-yne 1-iminium triflate salts and o-, m- or p-nitroaniline. These reactions include an aza-Michael reaction at room temperature followed by an intramolecular electrophilic aromatic substitution step, which requires additional thermal activation in most cases. In contrast, the conjugate addition of 2,4-dinitroanilines at the acetylenic iminium i

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19

Watson, Allan J. B., and David W. C. MacMillan. "ChemInform Abstract: Enantioselective Organocatalysis Involving Iminium, Enamine, Somo, and Photoredox Activation." ChemInform 42, no. 26 (2011): no. http://dx.doi.org/10.1002/chin.201126206.

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20

Dilman, Alexander D., Vitalij V. Levin, Miriam Karni, and Yitzhak Apeloig. "Activation of Pentafluorophenylsilanes by Weak Lewis Bases in Reaction with Iminium Cations." Journal of Organic Chemistry 71, no. 19 (2006): 7214–23. http://dx.doi.org/10.1021/jo0606812.

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21

Sparr, Christof, and Ryan Gilmour. "ChemInform Abstract: Cyclopropyl Iminium Activation: Reactivity Umpolung in Enantioselective Organocatalytic Reaction Design." ChemInform 43, no. 1 (2011): no. http://dx.doi.org/10.1002/chin.201201042.

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22

Holland, Mareike C., Jan Benedikt Metternich, Constantin Daniliuc, W. Bernd Schweizer, and Ryan Gilmour. "Aromatic Interactions in Organocatalyst Design: Augmenting Selectivity Reversal in Iminium Ion Activation." Chemistry - A European Journal 21, no. 28 (2015): 10031–38. http://dx.doi.org/10.1002/chem.201500270.

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23

Holland, Mareike C., Jan Benedikt Metternich, Constantin Daniliuc, W. Bernd Schweizer, and Ryan Gilmour. "Aromatic Interactions in Organocatalyst Design: Augmenting Selectivity Reversal in Iminium Ion Activation." Chemistry - A European Journal 21, no. 28 (2015): 9937. http://dx.doi.org/10.1002/chem.201501468.

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24

Jiang, Lin, Wen-Fei Jin, Liu-Dong Yu, et al. "Regioselective synthesis of benzonitriles via amino-catalyzed [3+3] benzannulation reaction." Journal of Chemical Research 44, no. 9-10 (2020): 592–97. http://dx.doi.org/10.1177/1747519820915163.

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A straightforward synthesis of benzonitriles is achieved via amino-catalyzed [3+3] benzannulation of α,β-unsaturated aldehydes and 4-arylsulfonyl-2-butenenitriles. Using pyrrolidine as an organocatalyst via iminium activation, a series of substituted benzonitriles were obtained in good to high yields in a regioselective manner. This reaction can proceed smoothly under mild reaction conditions and without the aid of any metals, additional oxidants, or strong bases, thus making this an efficient and environmentally friendly method to access benzonitriles.

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25

Easwar, Srinivasan, Ajit Jha, and Heena Inani. "A Nucleophilic Activation of Carboxylic Acids by Proline: Oxa-Michael Addition to Methyl Vinyl Ketone under Solvent-Free Conditions." Synlett 28, no. 12 (2017): 1473–77. http://dx.doi.org/10.1055/s-0036-1588172.

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A serendipitous nucleophilic activation of carboxylic acids by proline helped to achieve a direct hydrocarboxylation of methyl vinyl ketone at 60 °C under solvent-free conditions. A variety of carboxylic acids were used successfully in this oxa-Michael addition, affording useful 4-acyloxy-2-butanones in moderate yields. The reactions are carried out under solvent-free conditions, and the products are isolated in high purity by a simple work-up procedure without any need for column chromatographic purification, imparting a green quotient to the protocol. A heterodimeric non-covalent interaction

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26

Tan, Choon-Hong, Bo Teng, and Wei Lim. "Recent Advances in Enantioselective Brønsted Base Organocatalytic Reactions." Synlett 28, no. 11 (2017): 1272–77. http://dx.doi.org/10.1055/s-0036-1588847.

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Enantioselective Brønsted base catalyzed reactions have established themselves as powerful tools for the construction of optically pure compounds. Most strategies aim at improving these reactions involve the modification of substrates to decrease the pK a of the acidic proton. Typically, an electron-withdrawing group such as an ester or a fluorine is placed at the α-carbon, where the proton is also residing. The activation of less active proton, thus, becomes a major challenge in this field of research. In order to overcome this pK a barrier, some new innovative approaches have been demonstrat

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27

Melchiorre, Paolo, та Giuseppe Bartoli. "A Novel Organocatalytic Tool for the Iminium Activation of α,β-Unsaturated Ketones". Synlett 2008, № 12 (2008): 1759–72. http://dx.doi.org/10.1055/s-2008-1078503.

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28

Gao, Xin-Yue, Ru-Jie Yan, Ben-Xian Xiao, Wei Du, Łukasz Albrecht, and Ying-Chun Chen. "Asymmetric Formal Vinylogous Iminium Ion Activation for Vinyl-Substituted Heteroaryl and Aryl Aldehydes." Organic Letters 21, no. 23 (2019): 9628–32. http://dx.doi.org/10.1021/acs.orglett.9b03794.

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29

Morales, Sara. "Preparation of N-Sulfinyl Aldimines using Pyrrolidine as Catalyst via Iminium Ion Activation." Organic Syntheses 94 (2017): 346–57. http://dx.doi.org/10.15227/orgsyn.094.0346.

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30

Jiang, Lin, Hang Li, Jiang-Feng Zhou, et al. "Secondary amine-catalyzed [3 + 3] benzannulation to access polysubstituted benzenes through iminium activation." Synthetic Communications 48, no. 3 (2018): 336–43. http://dx.doi.org/10.1080/00397911.2017.1402351.

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31

Chau, Stephen T., J. Patrick Lutz, Kevin Wu, and Abigail G. Doyle. "Nickel‐Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode." Angewandte Chemie 125, no. 35 (2013): 9323–26. http://dx.doi.org/10.1002/ange.201303994.

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32

Palomo, Claudio, Aitor Landa, Antonia Mielgo, Mikel Oiarbide, Ángel Puente, and Silvia Vera. "Water-Compatible Iminium Activation: Organocatalytic Michael Reactions of Carbon-Centered Nucleophiles with Enals." Angewandte Chemie International Edition 46, no. 44 (2007): 8431–35. http://dx.doi.org/10.1002/anie.200703261.

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33

Chau, Stephen T., J. Patrick Lutz, Kevin Wu, and Abigail G. Doyle. "Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode." Angewandte Chemie International Edition 52, no. 35 (2013): 9153–56. http://dx.doi.org/10.1002/anie.201303994.

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34

Palomo, Claudio, Aitor Landa, Antonia Mielgo, Mikel Oiarbide, Ángel Puente, and Silvia Vera. "Water-Compatible Iminium Activation: Organocatalytic Michael Reactions of Carbon-Centered Nucleophiles with Enals." Angewandte Chemie 119, no. 44 (2007): 8583–87. http://dx.doi.org/10.1002/ange.200703261.

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35

Kalek, Marcin, Manoj Ghosh, and Adam Rajkiewicz. "Organocatalytic Group Transfer Reactions with Hypervalent Iodine Reagents." Synthesis 51, no. 02 (2018): 359–70. http://dx.doi.org/10.1055/s-0037-1609639.

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In recent years, a plethora of synthetic methods that employ hypervalent iodine compounds donating an atom or a group of atoms to an acceptor molecule have been developed. Several of these transformations utilize organocatalysis, which complements well the economic and environmental advantages offered by iodine reagents. This short review provides a systematic survey of the organocatalytic approaches that have been used to promote group transfer from hypervalent iodine species. It covers both the reactions in which an organocatalyst is applied to activate the acceptor, as well as those that ex

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36

Tian, Xu, Yankai Liu, and Paolo Melchiorre. "Aminocatalytic Enantioselective 1,6 Additions of Alkyl Thiols to Cyclic Dienones: Vinylogous Iminium Ion Activation." Angewandte Chemie 124, no. 26 (2012): 6545–48. http://dx.doi.org/10.1002/ange.201202392.

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37

Mukherjee, Shirshendu, and Bhaskar Biswas. "Organo‐Cascade Catalysis: Application of Merged Iminium‐Enamine Activation Technique and Related Cascade Reactivities." ChemistrySelect 5, no. 34 (2020): 10704–26. http://dx.doi.org/10.1002/slct.202003070.

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38

Tian, Xu, Yankai Liu, and Paolo Melchiorre. "Aminocatalytic Enantioselective 1,6 Additions of Alkyl Thiols to Cyclic Dienones: Vinylogous Iminium Ion Activation." Angewandte Chemie International Edition 51, no. 26 (2012): 6439–42. http://dx.doi.org/10.1002/anie.201202392.

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39

Holland, Mareike C., Jan Benedikt Metternich, Constantin Daniliuc, W. Bernd Schweizer, and Ryan Gilmour. "ChemInform Abstract: Aromatic Interactions in Organocatalyst Design: Augmenting Selectivity Reversal in Iminium Ion Activation." ChemInform 46, no. 45 (2015): no. http://dx.doi.org/10.1002/chin.201545022.

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40

List, Benjamin, Vijay N. Wakchaure, and Carla Obradors. "Chiral Brønsted Acids Catalyze Asymmetric Additions to Substrates that Are Already Protonated: Highly Enantioselective Disulfonimide-Catalyzed Hantzsch Ester Reductions of NH–Imine Hydrochloride Salts." Synlett 31, no. 17 (2020): 1707–12. http://dx.doi.org/10.1055/s-0040-1706413.

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While imines are frequently used substrates in asymmetric Brønsted acid catalysis, their corresponding salts are generally considered unsuitable reaction partners. Such processes are challenging because they require the successful competition of a catalytic amount of a chiral anion with a stoichiometric amount of an achiral one. We now show that enantiopure disulfonimides enable the asymmetric reduction of N–H imine hydrochloride salts using Hantzsch esters as hydrogen source. Our scalable reaction delivers crystalline primary amine salts in great efficiency and enantioselectivity and the disc

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41

Rueping, Magnus, Henrik Sundén, and Erli Sugiono. "Unifying Metal- and Organocatalysis for Asymmetric Oxidative Iminium Activation: A Relay Catalytic System Enabling the Combined Allylic Oxidation of Alcohols and Prolinol Ether Catalyzed Iminium Reactions." Chemistry - A European Journal 18, no. 12 (2012): 3649–53. http://dx.doi.org/10.1002/chem.201102551.

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42

Xiao, Ben-Xian, Ru-Jie Yan, Xin-Yue Gao, Wei Du, and Ying-Chun Chen. "Asymmetric Benzylic Functionalizations of 3-Vinyl Benzofurans via Cascade Formal Trienamine–Vinylogous Iminium Ion Activation." Organic Letters 19, no. 17 (2017): 4652–55. http://dx.doi.org/10.1021/acs.orglett.7b02287.

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43

Chau, Stephen T., J. Patrick Lutz, Kevin Wu, and Abigail G. Doyle. "ChemInform Abstract: Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode." ChemInform 45, no. 4 (2014): no. http://dx.doi.org/10.1002/chin.201404148.

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44

Mao, Zhifeng, Yaomei Jia, Wenyi Li та Rui Wang. "Water-Compatible Iminium Activation: Highly Enantioselective Organocatalytic Michael Addition of Malonates to α,β-Unsaturated Enones". Journal of Organic Chemistry 75, № 21 (2010): 7428–30. http://dx.doi.org/10.1021/jo101188m.

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45

Roudier, Mylène, Thierry Constantieux, Adrien Quintard, and Jean Rodriguez. "Triple Iron/Copper/Iminium Activation for the Efficient Redox Neutral Catalytic Enantioselective Functionalization of Allylic Alcohols." ACS Catalysis 6, no. 8 (2016): 5236–44. http://dx.doi.org/10.1021/acscatal.6b01102.

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46

Tian, Xu, Yankai Liu, and Paolo Melchiorre. "ChemInform Abstract: Aminocatalytic Enantioselective 1,6-Additions of Alkyl Thiols to Cyclic Dienones: Vinylogous Iminium Ion Activation." ChemInform 43, no. 43 (2012): no. http://dx.doi.org/10.1002/chin.201243074.

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47

Rueping, Magnus, Henrik Sunden, and Erli Sugiono. "ChemInform Abstract: Unifying Metal- and Organocatalysis for Asymmetric Oxidative Iminium Activation: A Relay Catalytic System Enabling the Combined Allylic Oxidation of Alcohols and Prolinol Ether Catalyzed Iminium Reactions." ChemInform 43, no. 30 (2012): no. http://dx.doi.org/10.1002/chin.201230027.

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48

Kunz, Roxanne K., and David W. C. MacMillan. "Enantioselective Organocatalytic Cyclopropanations. The Identification of a New Class of Iminium Catalyst Based upon Directed Electrostatic Activation." Journal of the American Chemical Society 127, no. 10 (2005): 3240–41. http://dx.doi.org/10.1021/ja042774b.

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49

Tomizawa, Motohiro, and John E. Casida. "NEONICOTINOID INSECTICIDE TOXICOLOGY: Mechanisms of Selective Action." Annual Review of Pharmacology and Toxicology 45, no. 1 (2005): 247–68. http://dx.doi.org/10.1146/annurev.pharmtox.45.120403.095930.

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The neonicotinoids, the newest major class of insecticides, have outstanding potency and systemic action for crop protection against piercing-sucking pests, and they are highly effective for flea control on cats and dogs. Their common names are acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam. They generally have low toxicity to mammals (acute and chronic), birds, and fish. Biotransformations involve some activation reactions but largely detoxification mechanisms. In contrast to nicotine, epibatidine, and other ammonium or iminium nicotinoids, whi

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50

Rodrigo, Eduardo, M. Belén Cid, Christian Roussel, et al. "A Proof of Concept: 2-Pyrazolines (4,5-Dihydro-1H-pyrazoles) Can Be Used as Organocatalysts via Iminium Activation." Letters in Organic Chemistry 13, no. 6 (2016): 414–19. http://dx.doi.org/10.2174/1570178613666160815163117.

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