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Journal articles on the topic 'Diazonium salts chemistry'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

Kasprzak, Artur, Agnieszka Zuchowska, and Magdalena Poplawska. "Functionalization of graphene: does the organic chemistry matter?" Beilstein Journal of Organic Chemistry 14 (August 2, 2018): 2018–26. http://dx.doi.org/10.3762/bjoc.14.177.

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Reactions applying amidation- or esterification-type processes and diazonium salts chemistry constitute the most commonly applied synthetic approaches for the modification of graphene-family materials. This work presents a critical assessment of the amidation and esterification methodologies reported in the recent literature, as well as a discussion of the reactions that apply diazonium salts. Common misunderstandings from the reported covalent functionalization methods are discussed, and a direct link between the reaction mechanisms and the basic principles of organic chemistry is taken into

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2

Oger, Nicolas, Erwan Le Grognec, and François-Xavier Felpin. "Handling diazonium salts in flow for organic and material chemistry." Organic Chemistry Frontiers 2, no. 5 (2015): 590–614. http://dx.doi.org/10.1039/c5qo00037h.

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3

Ahmad, Ahmad A. L., Bizuneh Workie, and Ahmed A. Mohamed. "Diazonium Gold Salts as Novel Surface Modifiers: What Have We Learned So Far?" Surfaces 3, no. 2 (2020): 182–96. http://dx.doi.org/10.3390/surfaces3020014.

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The challenges of diazonium salts stabilization have been overcome by their isolation as metal salts such as tetrachloroaurate(III). The cleavage of molecular nitrogen from diazonium salts even at very low potential or on reducing surfaces by fine tuning the substituents on the phenyl ring expanded their applications as surface modifiers in forensic science, nanomedicine engineering, catalysis and energy. The robustness of the metal–carbon bonding produced from diazonium salts reduction has already opened an era for further applications. The integration of experimental and calculations in this

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4

Huang, Jing, Zhenyao Yin, and Jinggao Wu. "Covalent attachment of chitosan to graphene via click chemistry for superior antibacterial activity." Materials Advances 1, no. 4 (2020): 579–83. http://dx.doi.org/10.1039/d0ma00082e.

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5

Ledenyova, I. V., V. V. Didenko, and Kh S. Shikhaliev. "Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*." Chemistry of Heterocyclic Compounds 50, no. 9 (2014): 1214–43. http://dx.doi.org/10.1007/s10593-014-1585-1.

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6

Servinis, Linden, Kathleen M. Beggs, Thomas R. Gengenbach, et al. "Tailoring the fibre-to-matrix interface using click chemistry on carbon fibre surfaces." Journal of Materials Chemistry A 5, no. 22 (2017): 11204–13. http://dx.doi.org/10.1039/c7ta00922d.

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A convenient and effective strategy to control the surface chemistry of carbon fibres is presented, comprising electro-chemical reduction of aryl diazonium salts onto the surface, followed by ‘click chemistry’ to tether the desired surface characteristic of choice.

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7

Luo, Yun, Yu Xiao, Delphine Onidas, et al. "Raman reporters derived from aryl diazonium salts for SERS encoded-nanoparticles." Chemical Communications 56, no. 50 (2020): 6822–25. http://dx.doi.org/10.1039/d0cc02842h.

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8

Josefík, František, Markéta Svobodová, Valerio Bertolasi, and Petr Šimůnek. "A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates." Beilstein Journal of Organic Chemistry 9 (July 23, 2013): 1463–71. http://dx.doi.org/10.3762/bjoc.9.166.

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Easily obtainable cyclic enaminones (piperidin-2-ylidenealkanones) can be transformed into substituted bicyclic pyridazinium tetrafluoroborates upon treatment with corresponding diazonium salts. The transformation can be performed either in a one-pot way or in a two-step process with the isolation of single azo-coupled enaminone as the intermediate. The former method is superior. Under the optimized conditions, a number of pyridazinium salts substituted with both electron-donating and electron-withdrawing substituents was easily synthesized. A mechanism of the formation of the pyridazinium sal

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9

Habraken, Evi, Andrew Jupp, and J. Slootweg. "Diazonium Salts as Nitrogen-Based Lewis Acids." Synlett 30, no. 08 (2019): 875–84. http://dx.doi.org/10.1055/s-0037-1612109.

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Aryldiazonium salts are widely used in many organic transformations with displacement of N2 or through addition to the terminal nitrogen. Such aryldiazonium salts can be viewed as N-based Lewis acids that can react with Lewis bases to synthesize a wide variety of azo compounds. Additionally, diazonium salts are known to undergo single-electron transfer and release N2, forming an aryl radical, which results in different reactivity. Herein, we provide a concise overview of the reactivity of aryldiazonium salts undergoing classical donor-acceptor reactivity or single-electron transfer.

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10

Paulus, Geraldine L. C., Qing Hua Wang, and Michael S. Strano. "Covalent Electron Transfer Chemistry of Graphene with Diazonium Salts." Accounts of Chemical Research 46, no. 1 (2012): 160–70. http://dx.doi.org/10.1021/ar300119z.

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11

Xu, Jian-Xing, Robert Franke, and Xiao-Feng Wu. "Phosphite-catalyzed alkoxycarbonylation of aryl diazonium salts." Organic & Biomolecular Chemistry 16, no. 34 (2018): 6180–82. http://dx.doi.org/10.1039/c8ob01744a.

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12

Liu, Guozhen. "Modification of Aryldiazonium Salts on Electrodes towards Designing Stable and Versatile Sensing Interfaces." Australian Journal of Chemistry 64, no. 5 (2011): 658. http://dx.doi.org/10.1071/ch11002.

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This paper reports the strategy of electrochemically reductive adsorption of aryldiazonium salts on electrodes for designing stable sensing interface. The diazonium salt chemistry can serve as an alternative system to alkanethiol-gold chemistry for the modification of electrode surfaces for biosensor applications.

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13

Gam-Derouich, Sarra, Jean Pinson, Philippe Decorse, et al. "Diazonium salt chemistry for the design of nano-textured anti-icing surfaces." Chemical Communications 54, no. 65 (2018): 8983–86. http://dx.doi.org/10.1039/c8cc02601g.

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Aryl diazonium salts have emerged as a new generation of robust surface modifiers for a wide range of applications. In this paper, we explore their potentialities to impart anti-icing properties to nano-textured copper surfaces.

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14

Shahnavaz, Zohreh, Lia Zaharani, Mohd Rafie Johan, and Nader Ghaffari Khaligh. "A Green Alternative for Aryl Iodide Preparation from Aromatic Amines." Current Organic Synthesis 17, no. 2 (2020): 131–35. http://dx.doi.org/10.2174/1570179417666200203121437.

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Background: In continuation of our previous work and the applications of saccharin, we encouraged to investigate the one-pot synthesis of the aryl iodides by the diazotization of the arene diazonium saccharin salts. Objective: Arene diazonium salts play an important role in organic synthesis as intermediate and a wide variety of aromatic compounds have been prepared using them. A serious drawback of arene diazonium salts is their instability in a dry state; therefore, they must be stored and handled carefully to avoid spontaneous explosion and other hazard events. Methods: The arene diazonium

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15

Kurasawa, Yoshihisa, and Atsushi Takada. "Synthesis of Quinoxalines Utilizing Aryl Diazonium Salts." HETEROCYCLES 24, no. 1 (1986): 232. http://dx.doi.org/10.3987/r-1986-01-0232.

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16

Saez, Rebeca, M. Dolores Otero, Belen Batanero, and Fructuoso Barba. "Microwave reaction of diazonium salts with nitriles." Journal of Chemical Research 2008, no. 9 (2008): 492–94. http://dx.doi.org/10.3184/030823408x340780.

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17

Kondratenko, P. A., T. A. Gordina, R. A. Mkhitarov, and E. N. Petrova. "Photocatalytic composition of diazonium salts in solution." Theoretical and Experimental Chemistry 20, no. 5 (1985): 543–48. http://dx.doi.org/10.1007/bf00522447.

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18

Al-Naggar, Abdul Aziz, Mervat Mohammed Abdel-Khalik, and Mohammed Hilmy Elnagdi. "Benzotriazol-1-yl-Acetone as a Building Block in Heterocyclic Chemistry: A Route to Benzotriazolylpyridazines, Benzotriazolylphthalazines and Benzotriazolylpyrazolo[5,1-c]-1,2,4-triazines." Journal of Chemical Research 23, no. 11 (1999): 648–49. http://dx.doi.org/10.1177/174751989902301106.

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Benzotriazolylacetone is coupled with aromatic diazonium salts to yield arylhydrazones, which can be condensed with ethyl cyanoacetate yielding pyridazinones whose reactivity towards activated double bond systems is investigated.

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19

Schmidt, Bernd, René Berger, and Frank Hölter. "Functionalized alkoxy arene diazonium salts from paracetamol." Organic & Biomolecular Chemistry 8, no. 6 (2010): 1406. http://dx.doi.org/10.1039/b924619c.

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20

Ledenyova, I. V., V. V. Didenko, and Kh S. Shikhaliev. "ChemInform Abstract: Chemistry of Pyrazole-3(5)-diazonium Salts (Review)." ChemInform 46, no. 16 (2015): no. http://dx.doi.org/10.1002/chin.201516339.

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21

Gosset, Cyrille, Sylvain Pellegrini, Romain Jooris, Till Bousquet, and Lydie Pelinski. "Visible-Light-Mediated Hydroxycarbonylation of Diazonium Salts." Advanced Synthesis & Catalysis 360, no. 17 (2018): 3401–5. http://dx.doi.org/10.1002/adsc.201800532.

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22

Schirowski, Milan, Christoph Tyborski, Janina Maultzsch, Frank Hauke, Andreas Hirsch, and Jakub Goclon. "Reductive diazotation of carbon nanotubes: an experimental and theoretical selectivity study." Chemical Science 10, no. 3 (2019): 706–17. http://dx.doi.org/10.1039/c8sc03737j.

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23

Moazzam, Ali, and Farnaz Jafarpour. "Chlorophyll-catalyzed photochemical regioselective coumarin C–H arylation with diazonium salts." New Journal of Chemistry 44, no. 39 (2020): 16692–96. http://dx.doi.org/10.1039/d0nj02012e.

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24

Krause, Andreas, Eric Sperlich, and Bernd Schmidt. "Matsuda–Heck arylation of itaconates: a versatile approach to heterocycles from a renewable resource." Organic & Biomolecular Chemistry 19, no. 19 (2021): 4292–302. http://dx.doi.org/10.1039/d1ob00392e.

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25

Tatunashvili, Elene, Bun Chan, Philippe E. Nashar та Christopher S. P. McErlean. "σ-Bond initiated generation of aryl radicals from aryl diazonium salts". Organic & Biomolecular Chemistry 18, № 9 (2020): 1812–19. http://dx.doi.org/10.1039/d0ob00205d.

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26

Bhojane, Jeevan Manohar, Vilas Gangadhar Jadhav, and Jayashree Milind Nagarkar. "Pd(NHC)PEPPSI-diazonium salts: an efficient blend for the decarboxylative Sonogashira cross coupling reaction." New Journal of Chemistry 41, no. 14 (2017): 6775–80. http://dx.doi.org/10.1039/c7nj00877e.

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27

Mezour, M. A., Y. Oweis, A. A. El-Hadad, S. Algizani, F. Tamimi, and M. Cerruti. "Surface modification of CoCr alloys by electrochemical reduction of diazonium salts." RSC Advances 8, no. 41 (2018): 23191–98. http://dx.doi.org/10.1039/c8ra02634c.

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28

Abdelrazek, Fathy Mohamed, and Ahmed Ali Fadda. "Nitriles in Heterocyclic Synthesis: A Novel Synthesis of Polyfunctionally Substituted Pyrrole Derivatives." Zeitschrift für Naturforschung B 41, no. 4 (1986): 499–501. http://dx.doi.org/10.1515/znb-1986-0416.

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29

Gribanov, Pavel S., Maxim A. Topchiy, Yulia D. Golenko, et al. "An unprecedentedly simple method of synthesis of aryl azides and 3-hydroxytriazenes." Green Chemistry 18, no. 22 (2016): 5984–88. http://dx.doi.org/10.1039/c6gc02379g.

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30

McLaren, Rachel L., Christian J. Laycock, David J. Morgan, and Gareth R. Owen. "Boronic acids for functionalisation of commercial multi-layer graphitic material as an alternative to diazonium salts." New Journal of Chemistry 44, no. 44 (2020): 19144–54. http://dx.doi.org/10.1039/d0nj04187d.

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Commercially obtained plasma-synthesised multi-layer graphene was functionalised with 4-(trifluoromethyl)phenyl groups utilising the corresponding boronic acid providing a safer alternative to diazonium salts.

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31

Zhang, Xin, Yaoyao Mei, Yangyang Li, Jingang Hu, Dayun Huang, and Yicheng Bi. "Visible‐Light‐Mediated Functionalization of Aryl Diazonium Salts." Asian Journal of Organic Chemistry 10, no. 3 (2021): 453–63. http://dx.doi.org/10.1002/ajoc.202000636.

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32

Jin, Cheng, Lianzheng Su, Daxi Ma, and Mingrong Cheng. "Transition-metal-free, visible-light-mediated cyclization of o-azidoarylalkynes with aryl diazonium salts." New Journal of Chemistry 41, no. 23 (2017): 14053–56. http://dx.doi.org/10.1039/c7nj03144k.

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A visible-light promoted transformation of o-azidoarylalkynes and aryl diazonium salts for the synthesis of unsymmetrical 2,3-diaryl-substituted indoles under transition-metal-free conditions was described.

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33

Halámek, Emil, and Zbyněk Kobliha. "Extraction Spectrophotometric Determination of [(2-Chlorophenyl)methylene]propane Dinitrile with Reactive Dyes of the Stabilized Diazonium Salt Type." Collection of Czechoslovak Chemical Communications 57, no. 6 (1992): 1221–29. http://dx.doi.org/10.1135/cccc19921221.

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A spectrophotometric method has been developed for the determination of [(2-chlorophenyl)methylene]propane dinitrile (CS) stabilized by the diazonium salts Fast Red TR and Fast Blue B after extraction with chloroform. Mass spectrometry, 1H and 13C NMR and elemental analysis confirmed the presence of the hydrazoform of the azo dye formed by reaction with malononitrile, as a product of the alkaline hydrolysis of substance CS, and the diazonium salt Fast Red TR.

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34

Yu, Xiuling, Peter Metz, and Horst Hartmann. "A simple route to 2-aryl-substituted naphtho[2,1-e][1,2,4]triazinium and naphtho[2,1-e][1,2,3,4]tetrazinium salts from 1-arylazo-substituted 2-naphthylamines." Zeitschrift für Naturforschung B 73, no. 7 (2018): 431–35. http://dx.doi.org/10.1515/znb-2018-0003.

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Abstract 1-Arylazo-substituted 2-naphthylamines, which are easily obtainable by the coupling of arene diazonium salts with 2-aminonaphthalene-sulfonic acid, can be transformed by reaction with reactive carboxylic acid derivatives or nitrosation reagents into novel 2-aryl-substituted naphtho[2,1-e][1,2,4]triazinium and naphtho[2,1-e][1,2,3,4]tetrazinium salts, respectively.

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35

Heimburger, Doriane, Sarra Gam-Derouich, Philippe Decorse, Claire Mangeney, and Jean Pinson. "Reversible Trapping of Functional Molecules at Interfaces Using Diazonium Salts Chemistry." Langmuir 32, no. 38 (2016): 9714–21. http://dx.doi.org/10.1021/acs.langmuir.6b02468.

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36

Zhu, Tong-Hao, Xiao-Chen Zhang, Kai Zhao, and Teck-Peng Loh. "Cu(OTf)2-mediated C(sp2)–H arylsulfonylation of enamides via the insertion of sulfur dioxide." Organic Chemistry Frontiers 6, no. 1 (2019): 94–98. http://dx.doi.org/10.1039/c8qo01144c.

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37

Rečnik, Simon, Jurij Svete, and Branko Stanovnik. "Reactions of Quinolizine- and Pyridino[1,2–a]pyrimidine-3-diazonium Tetrafluoroborates with Aliphatic Amines." Zeitschrift für Naturforschung B 59, no. 4 (2004): 380–85. http://dx.doi.org/10.1515/znb-2004-0405.

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KeywordsReactions of 1-cyano-4-oxo-4H-quinolizine-3-diazonium tetrafluoroborate (1a) and 4-oxo-4Hpyridino[ 1,2-a]pyrimidine-3-diazonium tetrafluoroborate (1b) with aliphatic amines 2a - g were studied. Treatment of heteroaryldiazonium salts 1 with secondary amines 2a - d afforded the corresponding N-alkyl-N’-heteroaryltriazenes 3a - h in high yields. On the other hand, reactions of 1a with aliphatic primary amines 2e - g resulted in an unexpected rearrangements into the corresponding picolinic acid N-alkylcarboxamides 4a - c.

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38

Troian-Gautier, Ludovic, Alice Mattiuzzi, Olivia Reinaud, Corinne Lagrost, and Ivan Jabin. "Use of calixarenes bearing diazonium groups for the development of robust monolayers with unique tailored properties." Organic & Biomolecular Chemistry 18, no. 19 (2020): 3624–37. http://dx.doi.org/10.1039/d0ob00070a.

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Calixarene-based diazonium salts can be easily synthesized in a few steps. This review surveys recent examples that illustrate the key advantages of these highly reactive molecular platforms for surface modification.

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39

Hafiz, I. S. Abdel, A. A. Hassanien, and A. M. Hussein. "Alkyl Heteroaromatics as Building Blocks in Organic Synthesis: The Reactivity of Alkyl Azoles toward Electrophilic Reagents." Zeitschrift für Naturforschung B 54, no. 7 (1999): 923–28. http://dx.doi.org/10.1515/znb-1999-0716.

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Oxazolone (1) couples with aromatic diazonium salts to yield the arylhydrazones (3a-c). Compound 3 reacts with aniline to give aryl hydrazone (5). Compound 5 was also obtained via converting 1 into the imidazolone (4) and subsequent treatment of 4 with aromatic diazonium salts. Compounds 1 and 12 reacted with arylidenemalononitrile (6) to yield compounds 8 and 14 respectively. Also compounds 1, 12 condensed with an aromatic aldehydes to yield 11 and 17. Compounds 11, 17 reacted further with one molecule of malononitrile to give compounds 8 and 14, respectively. Compound 20 which was generated

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40

Fedenok, Lidiya G., and Nataliya A. Zolnikova. "On the cyclization of ortho-alkynylbenzene diazonium salts." Tetrahedron Letters 44, no. 29 (2003): 5453–55. http://dx.doi.org/10.1016/s0040-4039(03)01295-4.

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41

Barba, Fructuoso, Fernando Ranz, and Belen Batanero. "Electrochemical transformation of diazonium salts into diaryl disulfides." Tetrahedron Letters 50, no. 49 (2009): 6798–99. http://dx.doi.org/10.1016/j.tetlet.2009.09.102.

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42

Liu, Yu, Ren-Jie Song, and Jin-Heng Li. "Palladium-catalyzed dearomatizative [2 + 2 + 1] carboannulation of 1,7-enynes with aryl diazonium salts and H2O: facile synthesis of spirocyclohexadienone-fused cyclopenta[c]quinolin-4(5H)-ones." Chemical Communications 53, no. 61 (2017): 8600–8603. http://dx.doi.org/10.1039/c7cc02830j.

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43

Chawla, Ruchi, and Lal Dhar S. Yadav. "Organic photoredox catalysis enabled cross-coupling of arenediazonium and sulfinate salts: synthesis of (un)symmetrical diaryl/alkyl aryl sulfones." Organic & Biomolecular Chemistry 17, no. 19 (2019): 4761–66. http://dx.doi.org/10.1039/c9ob00864k.

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Transition-metal- and oxidant/reductant-free visible-light-mediated synthesis of (un)symmetrical diaryl/alkyl aryl sulfones from aryl diazonium and sulfinate salts employing eosin Y as an organo-photoredox catalyst is reported.

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44

Xuan, Shangci, Xiaodan Wang, Jianwei Wang, Baoli Zhao, Kai Cheng, and Chenze Qi. "Research Progress on Cross-Coupling with Aryl Diazonium Salts." Chinese Journal of Organic Chemistry 34, no. 9 (2014): 1743. http://dx.doi.org/10.6023/cjoc201404004.

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45

Zhilin, Egor S., Leonid L. Fershtat, Dmitry M. Bystrov, et al. "Renaissance of 1,2,5-Oxadiazolyl Diazonium Salts: Synthesis and Reactivity." European Journal of Organic Chemistry 2019, no. 26 (2019): 4248–59. http://dx.doi.org/10.1002/ejoc.201900622.

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46

Heinrich, Markus R., Olga Blank, and Sabrina Wölfel. "Reductive Carbodiazenylation of Nonactivated Olefins via Aryl Diazonium Salts." Organic Letters 8, no. 15 (2006): 3323–25. http://dx.doi.org/10.1021/ol0611393.

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47

Bergbreiter, David E., and Nilusha Priyadarshani. "Syntheses of terminally functionalized polyisobutylene derivatives using diazonium salts." Journal of Polymer Science Part A: Polymer Chemistry 49, no. 8 (2011): 1772–83. http://dx.doi.org/10.1002/pola.24601.

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48

Oger, Nicolas, Erwan Le Grognec, and Francois-Xavier Felpin. "ChemInform Abstract: Handling Diazonium Salts in Flow for Organic and Material Chemistry." ChemInform 46, no. 29 (2015): no. http://dx.doi.org/10.1002/chin.201529318.

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49

Kuprat, Marcus, Axel Schulz, and Alexander Villinger. "Arsa-Diazonium Salts With an Arsenic-Nitrogen Triple Bond." Angewandte Chemie International Edition 52, no. 28 (2013): 7126–30. http://dx.doi.org/10.1002/anie.201302725.

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50

Brown, D. Sean, Jason V. Jollimore, Marcus P. Merrin, Keith Vaughan, and Donald L. Hooper. "Formation of methyl 2-arylhydrazono-3-oxobutanoates and 2-arylhydrazono-3-oxobutanenitriles during the coupling reaction of arenediazonium ions with methyl 3-aminocrotonate and 3-aminocrotononitrile." Canadian Journal of Chemistry 73, no. 2 (1995): 169–75. http://dx.doi.org/10.1139/v95-025.

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Reaction of aryldiazonium salts with methyl 3-aminocrotonate (1) affords high yields of the methyl 2-arylhydrazono-3-oxobutanoates (4); analogous diazonium coupling with 3-aminocrotononitrile (2) gives the 2-arylhydrazono-3-oxobutanenitriles (5). The hydrazones are the product of diazonium coupling at the C2-vinylic carbon, concomitant with hydrolysis of the 3-amino substituent to the 3-oxo derivative; there is no evidence for the formation of a triazene (6), which would be the product of N-coupling. All hydrazones (4a–e and 5a–d) have been fully characterized by IR and 1H and 13C NMR spectros

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