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Journal articles on the topic 'Nucleophilic aromatic substitution'

Author: Grafiati

Published: 4 June 2021

Last updated: 29 January 2023

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1

Christoffers, Jens, and Mathias S. Wickleder. "Synthesis of Aromatic and Aliphatic Di-, Tri-, and Tetrasulfonic Acids." Synlett 31, no. 10 (2020): 945–52. http://dx.doi.org/10.1055/s-0039-1691745.

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Oligosulfonic acids are promising linker compounds for coordination polymers and metal-organic frameworks, however, compared to their carboxylic acid congeners, often not readily accessible by established synthetic routes. This Account highlights the synthesis of recently developed aromatic and aliphatic di-, tri- and tetrasulfonic acids. While multiple electrophilic sulfonations of aromatic substrates are rather limited, the nucleophilic aromatic substitution including an intramolecular variant, the Newman–Kwart rearrangement, allows the flexible introduction of up to four sulfur-containing m

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2

Liljenberg, Magnus, Tore Brinck, Tobias Rein та Mats Svensson. "Utilizing the σ-complex stability for quantifying reactivity in nucleophilic substitution of aromatic fluorides". Beilstein Journal of Organic Chemistry 9 (23 квітня 2013): 791–99. http://dx.doi.org/10.3762/bjoc.9.90.

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A computational approach using density functional theory to compute the energies of the possible σ-complex reaction intermediates, the “σ-complex approach”, has been shown to be very useful in predicting regioselectivity, in electrophilic as well as nucleophilic aromatic substitution. In this article we give a short overview of the background for these investigations and the general requirements for predictive reactivity models for the pharmaceutical industry. We also present new results regarding the reaction rates and regioselectivities in nucleophilic substitution of fluorinated aromatics.

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3

Zhang, Xiao, Guo-ping Lu, and Chun Cai. "Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction." Green Chemistry 18, no. 20 (2016): 5580–85. http://dx.doi.org/10.1039/c6gc01742h.

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4

Sadowsky, Daniel, Kristopher McNeill, and Christopher J. Cramer. "Dehalogenation of Aromatics by Nucleophilic Aromatic Substitution." Environmental Science & Technology 48, no. 18 (2014): 10904–11. http://dx.doi.org/10.1021/es5028822.

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5

Flippin, Lec A., David S. Carter, and Nathan J. P. Dubree. "Nucleophilic aromatic substitution on aromatic aldimines." Tetrahedron Letters 34, no. 20 (1993): 3255–58. http://dx.doi.org/10.1016/s0040-4039(00)73675-6.

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6

Li, Jinhua, Zhengyu Lu, Yuhui Hua, Dafa Chen, and Haiping Xia. "Carbolong chemistry: nucleophilic aromatic substitution of a triflate functionalized iridapentalene." Chemical Communications 57, no. 68 (2021): 8464–67. http://dx.doi.org/10.1039/d1cc03261e.

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7

Baum, James Clayton, Jimat Bolhassan, Richard Francis Langler, Paul Joseph Pujol, and Raj Kumar Raheja. "Sulfonyl esters. 2. CS cleavage in some substitution reactions of nitrobenzenesulfonates." Canadian Journal of Chemistry 68, no. 8 (1990): 1450–55. http://dx.doi.org/10.1139/v90-222.

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An attempt to explore aromatic sulfonate esters as agents for the condensation of alcohols with mercaptans revealed an unusual process for sulfonate esters: CS bond rupture. Two mechanistic possibilities for CS bond rupture are explored: (i) radical anion intermediacy via single electron transfer and (ii) nucleophilic aromatic substitution. Both experiments and molecular orbital computations are presented to support the conclusion that nucleophilic aromatic substitutions are occurring. Keywords: sulfonyl esters, nitrobenzenesulfonates, CS bond rupture.

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8

Garçon, Martí, Clare Bakewell, Andrew J. P. White, and Mark R. Crimmin. "Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles." Chemical Communications 55, no. 12 (2019): 1805–8. http://dx.doi.org/10.1039/c8cc09701a.

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Reaction of nucleophiles containing polar (Fe–Mg) and apolar (Mg–Mg) bonds with 2-(pentafluorophenyl)pyridine are calculated to proceed by stepwise and concerted S<sub>N</sub>Ar pathways respectively.

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9

Vasilenko, Dmitry A., Sevastian E. Dronov, Dzianis U. Parfiryeu, et al. "5-Nitroisoxazoles in SNAr reactions: access to polysubstituted isoxazole derivatives." Organic & Biomolecular Chemistry 19, no. 29 (2021): 6447–54. http://dx.doi.org/10.1039/d1ob00816a.

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An efficient protocol for the straightforward functionalization of the isoxazole ring via the reactions of aromatic nucleophilic substitution of the nitro group with various nucleophiles has been elaborated.

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10

Ajenjo, Javier, Martin Greenhall, Camillo Zarantonello, and Petr Beier. "Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene." Beilstein Journal of Organic Chemistry 12 (February 3, 2016): 192–97. http://dx.doi.org/10.3762/bjoc.12.21.

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3-Fluoro-5-nitro-1-(pentafluorosulfanyl)benzene was prepared by three different ways: as a byproduct of direct fluorination of 1,2-bis(3-nitrophenyl)disulfane, by direct fluorination of 4-nitro-1-(pentafluorosulfanyl)benzene, and by fluorodenitration of 3,5-dinitro-1-(pentafluorosulfanyl)benzene. The title compound was subjected to a nucleophilic aromatic substitution of the fluorine atom with oxygen, sulfur and nitrogen nucleophiles affording novel (pentafluorosulfanyl)benzenes with 3,5-disubstitution pattern. Vicarious nucleophilic substitution of the title compound with carbon, oxygen, and

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11

Ross, Joseph P., Philippe Couture, and John Warkentin. "Nucleophilic aromatic substitution with dialkoxycarbenes." Canadian Journal of Chemistry 75, no. 10 (1997): 1331–35. http://dx.doi.org/10.1139/v97-159.

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Dimethoxycarbene, generated at 110 °C by thermolysis of 2,2-dimethoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazoline, displaces fluoride from aromatic rings that are activated with electron-withdrawing groups. Intermolecular substitution on Sanger's reagent and on hexafluorobenzene are reported, together with intramolecular substitution by a dioxycarbene with a tethered aryl group. Keywords: aromatic substitution, aryl(dimethoxy)fluoromethanes, aryl fluoride, dialkoxycarbene, nucleophilic substitution.

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12

Hudson, R., N. P. Bizier, K. N. Esdale, and J. L. Katz. "Synthesis of indoles, benzofurans, and related heterocycles via an acetylene-activated SNAr/intramolecular cyclization cascade sequence in water or DMSO." Organic & Biomolecular Chemistry 13, no. 8 (2015): 2273–84. http://dx.doi.org/10.1039/c4ob02549k.

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The synthesis of 2-substituted indoles and benzofurans was achieved by nucleophilic aromatic substitution, followed by subsequent 5-endo-dig cyclization between the nucleophile and an ortho acetylene.

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13

Bacaloglu, Radu, Clifford A. Bunton, and Giorgio Cerichelli. "Intermediates in nucleophilic aromatic substitution." Journal of the American Chemical Society 109, no. 2 (1987): 621–23. http://dx.doi.org/10.1021/ja00236a072.

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14

Rohrbach, Simon, Andrew J. Smith, Jia Hao Pang, et al. "Concerted Nucleophilic Aromatic Substitution Reactions." Angewandte Chemie International Edition 58, no. 46 (2019): 16368–88. http://dx.doi.org/10.1002/anie.201902216.

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15

Crampton, Michael R. "ChemInform Abstract: Nucleophilic Aromatic Substitution." ChemInform 31, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.200016310.

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16

CRAMPTON, M. R. "ChemInform Abstract: Nucleophilic Aromatic Substitution." ChemInform 26, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.199536311.

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17

Crampton, M. R. "ChemInform Abstract: Nucleophilic Aromatic Substitution." ChemInform 33, no. 50 (2010): no. http://dx.doi.org/10.1002/chin.200250268.

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18

Crampton, M. R. "ChemInform Abstract: Nucleophilic Aromatic Substitution." ChemInform 42, no. 46 (2011): no. http://dx.doi.org/10.1002/chin.201146252.

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19

Crampton, M. R. "ChemInform Abstract: Nucleophilic Aromatic Substitution." ChemInform 42, no. 26 (2011): no. http://dx.doi.org/10.1002/chin.201126239.

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20

CRAMPTON, M. R. "ChemInform Abstract: Nucleophilic Aromatic Substitution." ChemInform 24, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.199302302.

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21

CRAMPTON, M. R. "ChemInform Abstract: Nucleophilic Aromatic Substitution." ChemInform 22, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199133305.

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22

Zhang, Xiao, Guo-ping Lu, and Chun Cai. "Correction: Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction." Green Chemistry 18, no. 22 (2016): 6143. http://dx.doi.org/10.1039/c6gc90108e.

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Correction for ‘Facile aromatic nucleophilic substitution (S<sub>N</sub>Ar) reactions in ionic liquids: an electrophile–nucleophile dual activation by [Omim]Br for the reaction’ by Xiao Zhang, et al., Green Chem., 2016, 18, 5580–5585.

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23

Wang, Jianghong, Ashot Kh Khanamiryan, and Clifford C. Leznoff. "Multisubstituted phthalonitriles for phthalocyanine synthesis." Journal of Porphyrins and Phthalocyanines 08, no. 11 (2004): 1293–99. http://dx.doi.org/10.1142/s1088424604000660.

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3,4,5,6-tetrafluorophthalonitrile and 3,4,5,6-tetrachlorophthalonitrile were used as substrates with various phenoxides to prepare 3,4,6-trihalo-5-p-substitutedphenoxyphthalonitriles, containing four substituents other than hydrogen, by nucleophilic aromatic substitution reactions. Subsequent reactions with unsymmetrical catechols gave tetrasubstitutedphthalonitriles, having four different substituents. In one instance, attempts to displace the last remaining fluoro group by an octanoxide nucleophile led to substitution of a p-methylphenoxy group, showing that phenoxy substituents are also lab

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24

Amatore, Christian, Catherine Combellas, Jean Pinson, Jean-Michel Savéant, and André Thiébault. "Phenoxide ions as nucleophiles in SRN1 aromatic nucleophilic substitution." J. Chem. Soc., Chem. Commun., no. 1 (1988): 7–8. http://dx.doi.org/10.1039/c39880000007.

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25

Charushin, V. N., and O. N. Chupakhin. "SNH methodology and new approaches to condensed heterocyclic systems." Pure and Applied Chemistry 76, no. 9 (2004): 1621–31. http://dx.doi.org/10.1351/pac200476091621.

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The review surveys the reactions of electron-deficient azaaromatic compounds with mono- and bifunctional nucleophilies in which a nucleophilic attack at the unsubstituted CH carbon of an aromatic ring is one of the key steps. Use of the SNH methodology for the synthesis of fused heterocyclic systems by means of nucleophilic addition –addition AN–AN, addition –substitution of hydrogen AN–SNH, tandem substitution of hydrogen SNH–SNH, and other strategies will be discussed. Intramolecular SNH reactions will also be considered as effective synthetic tools to obtain condensed heterocyclic systems.

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26

Alam, Nayat, Christian Amatore, Catherine Combellas, et al. "Electrochemically catalyzed aromatic nucleophilic substitution. Phenoxide ion as nucleophile." Journal of Organic Chemistry 53, no. 7 (1988): 1496–504. http://dx.doi.org/10.1021/jo00242a029.

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27

Sbarbati Nudelman, N., and D. Palleros. "Evidence for A “Dimer” Nucleophile in Aromatic Nucleophilic Substitution." Bulletin des Sociétés Chimiques Belges 91, no. 5 (2010): 411. http://dx.doi.org/10.1002/bscb.19820910570.

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28

Mąkosza, Mieczysław. "How Does Nucleophilic Aromatic Substitution in Nitroarenes Really Proceed: General Mechanism." Synthesis 49, no. 15 (2017): 3247–54. http://dx.doi.org/10.1055/s-0036-1588444.

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On the basis of previously published experimental studies and ab initio calculations, a general corrected mechanism of nucleophilic aromatic substitution was formulated. It was shown that conventional nucleophilic substitution of halogens is a slow secondary reaction whereas nucleophilic substitution of hydrogen is the fast primary process. The general mechanism embraces both of these alternative and complementary reactions.

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29

FLIPPIN, L. A., D. S. CARTER, and N. J. P. DUBREE. "ChemInform Abstract: Nucleophilic Aromatic Substitution on Aromatic Aldimines." ChemInform 24, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199340092.

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30

Santos, Tanausú, David S. Rivero, Yaiza Pérez‐Pérez, et al. "Dynamic Nucleophilic Aromatic Substitution of Tetrazines." Angewandte Chemie 133, no. 34 (2021): 18931–39. http://dx.doi.org/10.1002/ange.202106230.

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31

Santos, Tanausú, David S. Rivero, Yaiza Pérez‐Pérez, et al. "Dynamic Nucleophilic Aromatic Substitution of Tetrazines." Angewandte Chemie International Edition 60, no. 34 (2021): 18783–91. http://dx.doi.org/10.1002/anie.202106230.

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32

G. Rasmussen, Paul, and Paul G. Apen. "Nucleophilic Aromatic substitution in 4,5-Dicyanoimidazoles." HETEROCYCLES 29, no. 7 (1989): 1325. http://dx.doi.org/10.3987/com-89-4980.

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33

Dotterer, Sally K., and Ronald L. Harris. "MNDO study of nucleophilic aromatic substitution." Journal of Organic Chemistry 53, no. 4 (1988): 777–79. http://dx.doi.org/10.1021/jo00239a015.

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34

Liljenberg, Magnus, Tore Brinck, Björn Herschend, Tobias Rein, Simone Tomasi, and Mats Svensson. "Predicting Regioselectivity in Nucleophilic Aromatic Substitution." Journal of Organic Chemistry 77, no. 7 (2012): 3262–69. http://dx.doi.org/10.1021/jo202569n.

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35

You, Fengxiang, and Robert J. Twieg. "Aromatic nucleophilic substitution with 4-hydroxypyridine." Tetrahedron Letters 40, no. 50 (1999): 8759–62. http://dx.doi.org/10.1016/s0040-4039(99)01694-9.

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36

Ong, Wen Jie, and Timothy M. Swager. "Dynamic self-correcting nucleophilic aromatic substitution." Nature Chemistry 10, no. 10 (2018): 1023–30. http://dx.doi.org/10.1038/s41557-018-0122-8.

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37

Abraham, Liza. "A Green Nucleophilic Aromatic Substitution Reaction." Journal of Chemical Education 97, no. 10 (2020): 3810–15. http://dx.doi.org/10.1021/acs.jchemed.0c00181.

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38

El Kassmi, A., G. Héraud, W. Büchner, F. Fache, and M. Lemaire. "Aromatic nucleophilic substitution on thiophene rings." Journal of Molecular Catalysis 72, no. 3 (1992): 299–305. http://dx.doi.org/10.1016/0304-5102(92)85007-3.

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39

Salamov, Ali Kh, Abdulakh K. Mikitaev, Aues A. Beev, Julietti A. Beeva, Mukhamed Kh Ligidov, and Sergey I. Pakhomov. "POLYARYLENEETHERKETONES OBTAINING WITH REACTION OF NUCLEOPHILIC SUBSTITUTION." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 59, no. 7 (2018): 4. http://dx.doi.org/10.6060/tcct.20165907.5389.

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The article deals with the study of influence of the synthesis conditions on the molecular weight of polyaryleneetherketones (PAEK), received with nucleophilic substitution reaction of activated aryl halide. The synthesis of PAEK with the nucleophilic substitution reaction carried out as partially hydrolyzed homopolycondensation of phenolates and aromatic dihalides containing a carbonyl group in the molecule and derivatives of polycondensation of aromatic bisphenols with activated aromatic dihalides, and aromatic nitro compounds. The nucleophilic substitution of halogen in aryldihalogens proce

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40

Gong, Liang-Chu, and David Dolphin. "Nucleophilic substitution of meso-nitrooctaethylporphyrins." Canadian Journal of Chemistry 63, no. 2 (1985): 406–11. http://dx.doi.org/10.1139/v85-067.

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Nitrooctaethylporphyrins readily undergo nucleophilic aromatic substitution in the presence of HCl or HBr. In the presence of methoxide, nucleophilic addition to give a porphodimethane occurs, followed by autoxidation to the methoxyporphyrin. Unlike the nitrated complexes, the chlorosubstituted porphyrins exhibit redox potentials similar to those of unsubstituted analogs. Meso-halogenated porphyrins do, however, show steric distortion due to the bulk of the halogen atoms.

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41

Lu, Xiaosong, and John Warkentin. "Mechanism of ipso aromatic substitution by reaction of aryloxy(methoxy)carbenes and diaryloxycarbenes with DMAD." Canadian Journal of Chemistry 79, no. 4 (2001): 364–69. http://dx.doi.org/10.1139/v01-029.

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Some aryloxy(methoxy)carbenes and diaryloxycarbenes attack dimethyl acetylenedicarboxylate (DMAD) with aryl group transfer to an alkyne carbon of DMAD. In this study diaryloxycarbenes with different aryl groups that could be transferred competitively, were generated in the presence of DMAD to probe for the mechanism of that ipso aromatic substitution. It was found that a para electron-withdrawing substituent, relative to an electron-donating substituent, facilitated migration of an aryl group. Mechanisms in accord with these findings involve initial nucleophilic attack by the carbene at an alk

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42

Okhlobystina, Aleksandra V., Andrey O. Okhlobystin, Nadezhda T. Berberova, and Daria A. Burmistrova. "HYDROGEN SULFIDE IN NUCLEOPHILIC SUBSTITUTION REACTIONS OF HYDROXY GROUPS IN AROMATIC ALCOHOLS." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENIY KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 61, no. 9-10 (2018): 36–41. http://dx.doi.org/10.6060/ivkkt.20186109-10.5716.

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Most methods of obtaining aromatic thiols are based on nucleophilic substitution reactions at halogen derivatives of aromatic hydrocarbons when used as nucleophilic reagents sodium thiolate, thiourea or potassium xanthate at high temperatures, pressure and in the presence of catalysts. The direct reaction of nucleophilic substitution of OH-groups in the phenols, pyrocatechol and benzyl alcohol to the HS-group in conditions of one-electron reducrion of hydrogen sulfide in acetonitrile and pyridinium ionic liquid was investigated for the first time. The proposed reactions proceed at room tempera

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43

Abd-El-Aziz, Alaa S., Christine R. de Denus, and Harold M. Hutton. "Ironcyclopentadienyl mediated 2-alkyl-2-arylphenylsulphonylacetonitrile synthesis." Canadian Journal of Chemistry 73, no. 2 (1995): 289–95. http://dx.doi.org/10.1139/v95-039.

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A unique route to the synthesis of 2-alkyl-2-arylphenylsulphonylacetonitriles via the nucleophilic aromatic substitution (SNAr) of chloroarene cyclopentadienyliron complexes with 2-alkyl phenylsulphonylacetonitriles has been investigated. Reactions of chloroarene complexes (1a–d) with 2-alkyl phenylsulphonylacetonitrile (2a,b) in the presence of K2CO3 in DMF at room temperature led to the formation of complexes 3a–d and 4a,c,d in good yields. The use of alkylated phenylsulphonylacetonitriles as nucleophiles in the reactions with the p-dichlorobenzene complex (1e) allowed the formation of the d

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44

Khutorianskyi, Viktor V., Norbert Baris, and Petr Beier. "Oxidative nucleophilic alkoxylation of nitrobenzenes." Organic Chemistry Frontiers 8, no. 1 (2021): 77–81. http://dx.doi.org/10.1039/d0qo01291b.

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45

Drew, Mark D., David A. Jackson, Nicholas J. Lawrence, John Liddle, and Robin G. Pritchard. "Asymmetric aromatic vicarious nucleophilic substitution of hydrogen." Chemical Communications, no. 2 (1997): 189–90. http://dx.doi.org/10.1039/a606921e.

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46

Engelhart, Jens U., Benjamin D. Lindner, Olena Tverskoy, Frank Rominger, and Uwe H. F. Bunz. "Partially Fluorinated Tetraazaacenes by Nucleophilic Aromatic Substitution." Journal of Organic Chemistry 78, no. 21 (2013): 10832–39. http://dx.doi.org/10.1021/jo401824g.

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47

Huber, Florian, Joel Roesslein, and Karl Gademann. "Preparation of Indolenines via Nucleophilic Aromatic Substitution." Organic Letters 21, no. 8 (2019): 2560–64. http://dx.doi.org/10.1021/acs.orglett.9b00489.

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48

Avila, Walter B., Jeffrey L. Crow, and Clifford M. Utermoehlen. "Nucleophilic aromatic substitution: A microscale organic experiment." Journal of Chemical Education 67, no. 4 (1990): 350. http://dx.doi.org/10.1021/ed067p350.

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49

Artamkina, G. A., A. Yu Mil'chenko, I. P. Beletskaya, and O. A. Reutov. "Transition metal carbonylates in nucleophilic aromatic substitution." Journal of Organometallic Chemistry 311, no. 1-2 (1986): 199–206. http://dx.doi.org/10.1016/0022-328x(86)80233-9.

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50

Whiddon, Christy R., Clifford A. Bunton, and Olle Soderman. "Aromatic nucleophilic substitution in nonionic alkylglucoside micelles." Journal of Colloid and Interface Science 278, no. 2 (2004): 461–64. http://dx.doi.org/10.1016/j.jcis.2004.06.018.

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