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Journal articles on the topic 'Arenediazonium salts'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 February 2022

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1

Sengupta, Saumitra, and Srinivasan Chandrasekaran. "Modifications of amino acids using arenediazonium salts." Organic & Biomolecular Chemistry 17, no. 36 (2019): 8308–29. http://dx.doi.org/10.1039/c9ob01471c.

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Aryl transfer reactions from arenediazonium salts have started to make their impact in chemical biology with initial forays in the arena of arylative modifications and bio-conjugations of amino acids, peptides and proteins.

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2

Pahovnik, David, Uroš Uršič, Uroš Grošelj, Anton Meden, Jurij Svete, and Branko Stanovnik. "Synthesis of Dimethyl 1-(Hetero)aryl-4-oxo-1,4-dihydropyridazine- 3,5-dicarboxylates from Dimethyl 3-Oxopentane-1,5-dioates." Zeitschrift für Naturforschung B 63, no. 4 (2008): 407–14. http://dx.doi.org/10.1515/znb-2008-0407.

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AbstractDimethyl 3-oxopentane-1,5-dioate (dimethyl acetone-1,3-dicarboxylate) (1) was transformed first with (hetero)arenediazonium salts 3a - j into dimethyl 2-[(hetero)arylhydrazono]pentane-1,5-dioates 4a - j followed by reaction with N,N-dimethylformamide dimethylacetal (DMFDMA) to afford, without isolation of intermediates 5a - j, dimethyl 1-(hetero)aryl-4-oxo-1,4-dihydropyridazine-3,5- dicarboxylates 6a - j. An alternative method represents transformation of 1 with DMFDMA into dimethyl 2-[(dimethylamino)methylidene]-3-oxopentane-1,5-dioate (7) followed by treatment with (hetero)arenediazo

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3

Felpin, François-Xavier, and Saumitra Sengupta. "Biaryl synthesis with arenediazonium salts: cross-coupling, CH-arylation and annulation reactions." Chemical Society Reviews 48, no. 4 (2019): 1150–93. http://dx.doi.org/10.1039/c8cs00453f.

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4

Wang, Xiaojun, Yajun Li, Yuwei Guo, Zhentong Zhu, Yongming Wu, and Weiguo Cao. "Direct isoperfluoropropylation of arenediazonium salts with hexafluoropropylene." Organic Chemistry Frontiers 3, no. 3 (2016): 304–8. http://dx.doi.org/10.1039/c5qo00388a.

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Perfluoropropylene can be used directly for isoperfluoropropylation of arenediazonium salts in the presence of silver fluoride and cuprous iodide. A practical tandem diazotization and isoperfluoropropylation protocol was developed for aniline derivatives to generate isoperfluoropropylarenes with good functional-group compatibility.

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5

Lampard, Christopher, John A. Murphy, Faiza Rasheed, Norman Lewis, Michael B. Hursthouse, and D. E. Hibbs. "Novel synthetic applications of arenediazonium salts." Tetrahedron Letters 35, no. 46 (1994): 8675–78. http://dx.doi.org/10.1016/s0040-4039(00)78469-3.

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6

Koizumi, Toshio, Nadeem Bashir, and John A. Murphy. "Reactions of Arenediazonium Salts with Diazadithiafulvalenes." Tetrahedron Letters 38, no. 43 (1997): 7635–38. http://dx.doi.org/10.1016/s0040-4039(97)01813-3.

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7

Fabrizi, Giancarlo, Antonella Goggiamani, Alessio Sferrazza, and Sandro Cacchi. "Sonogashira Cross-Coupling of Arenediazonium Salts." Angewandte Chemie 122, no. 24 (2010): 4161–64. http://dx.doi.org/10.1002/ange.201000472.

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8

Fabrizi, Giancarlo, Antonella Goggiamani, Alessio Sferrazza, and Sandro Cacchi. "Sonogashira Cross-Coupling of Arenediazonium Salts." Angewandte Chemie International Edition 49, no. 24 (2010): 4067–70. http://dx.doi.org/10.1002/anie.201000472.

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9

Matheis, Christian, Kévin Jouvin, and Lukas J. Goossen. "Sandmeyer Difluoromethylation of (Hetero-)Arenediazonium Salts." Organic Letters 16, no. 22 (2014): 5984–87. http://dx.doi.org/10.1021/ol5030037.

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10

Gracza, Tibor, Zdeněk Arnold, and Jaroslav Kováč. "Electrophilic ipso substitutions of furan vinamidinium salts." Collection of Czechoslovak Chemical Communications 53, no. 5 (1988): 1053–59. http://dx.doi.org/10.1135/cccc19881053.

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5-(N,N-Dialkylamino)-2-furfurylidene-N,N-dialkylimminium salts I (the vinamidinium salts of furan) react with arenediazonium salts to give products of ipso substitution in position 2 of the furan ring, i.e. 5-(N,N-dialkylamino)-2-azoarenefuran salts II. The structure of these products was evidenced by 1H NMR and UV spectral data.

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11

Wu, Wei, Xiaoyan Han, and Zhiqiang Weng. "Synthesis of pertrifluoromethyl pyridazine derivatives via a tandem reaction of aryldiazonium salts with hexafluoroacetylacetone." Organic Chemistry Frontiers 7, no. 21 (2020): 3499–504. http://dx.doi.org/10.1039/d0qo00955e.

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12

Carrillo-Arcos, Ulises A., and Susana Porcel. "Gold promoted arylative cyclization of alkynoic acids with arenediazonium salts." Organic & Biomolecular Chemistry 16, no. 11 (2018): 1837–42. http://dx.doi.org/10.1039/c7ob02447a.

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13

Gund, Sitaram Haribhau, Radheshyam Suresh Shelkar, and Jayashree Milind Nagarkar. "Copper catalyzed synthesis of unsymmetrical diaryl sulfones from an arenediazonium salt and sodium p-toluenesulfinate." RSC Advances 5, no. 77 (2015): 62926–30. http://dx.doi.org/10.1039/c5ra10291j.

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14

Chaudhari, Tohasib Yusub, Asik Hossian, Manash Kumar Manna, and Ranjan Jana. "Chemo-, regio-, and stereoselective Heck–Matsuda arylation of allylic alcohols under mild conditions." Organic & Biomolecular Chemistry 13, no. 17 (2015): 4841–45. http://dx.doi.org/10.1039/c5ob00235d.

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15

Schmidt, Bernd, Nastja Riemer, Christin Coswig, and Mike Shipman. "Palladium-Catalyzed Cross-Coupling of Arenediazonium Salts with Organoindium or Organobismuth Reagents." Synlett 29, no. 18 (2018): 2427–31. http://dx.doi.org/10.1055/s-0037-1611001.

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16

Chen, Zhen, Shuang-Qing Fan, Yan Zheng, and Jun-An Ma. "Silver-catalyzed regioselective [3+2] cycloaddition of arene-diazonium salts with 2,2,2-trifluorodiazoethane (CF3CHN2): a facile access to 2-aryl-5-trifluoromethyltetrazoles." Chemical Communications 51, no. 92 (2015): 16545–48. http://dx.doi.org/10.1039/c5cc07324c.

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17

Slepchenko, Galina B., Evgeniya S. Moiseeva, Elena V. Dorozhko, et al. "An electrochemical sensor for detecting selenium in biological fluids on an arenediazonium tosylate-modified metal electrode." Analytical Methods 13, no. 13 (2021): 1584–90. http://dx.doi.org/10.1039/d1ay00156f.

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18

Sugimoto, Takashi, and Wolfgang Pfleiderer. "Arylation of 1,3-Dimethyllumazines by Arenediazonium Salts." HETEROCYCLES 45, no. 4 (1997): 765. http://dx.doi.org/10.3987/com-97-7748.

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19

Pratsch, Gerald, Christian A. Anger, Katharina Ritter, and Markus R. Heinrich. "Hydroxy- and Aminophenyl Radicals from Arenediazonium Salts." Chemistry - A European Journal 17, no. 15 (2011): 4104–8. http://dx.doi.org/10.1002/chem.201003713.

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20

Chen, Shuangshuang, Zhangjin Pan, and Yan Wang. "PPh3-Mediated Borylation of Arenediazonium Salts with Bis(pinacolato)diborane." Zeitschrift für Naturforschung B 69, no. 9-10 (2014): 982–86. http://dx.doi.org/10.5560/znb.2014-4139.

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AbstractA metal-free, PPh3-mediated borylation reaction of arenediazonium salts with bis(pinacolato)diborane has been developed under mild conditions. The process provides an attractive alternative to the traditional preparation of arylboronates, albeit in moderate yields

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21

Asomoza-Solís, Eric Omar, Jonathan Rojas-Ocampo, Rubén Alfredo Toscano, and Susana Porcel. "Arenediazonium salts as electrophiles for the oxidative addition of gold(i)." Chemical Communications 52, no. 45 (2016): 7295–98. http://dx.doi.org/10.1039/c6cc03105f.

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Arenediazonium salts have been found to behave as efficient electrophiles for the oxidation of gold(i). Starting from anilines, a one pot cross-coupling reaction of anilines with silver acetylides mediated by gold has been developed.

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22

Elnagdi, Mohamed Hilmy, Kamal Usef Sadek, Nadia Mohamed Taha, and Youssef Mahfous Yassin. "The structure of products of coupling of arenediazonium salts with 3-aminocrotononitrile derivatives." Collection of Czechoslovak Chemical Communications 55, no. 3 (1990): 734–44. http://dx.doi.org/10.1135/cccc19900734.

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The structure of products of coupling arenediazonium salts with 3-aminocrotononitrile derivatives is reported. The spectral data as well as the chemical behaviour of coupling products indicated that it is the hydrazone in (E)-form.

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23

Ju, Baihang, Shigui Chen, and Wangqing Kong. "Enantioselective palladium-catalyzed diarylation of unactivated alkenes." Chemical Communications 55, no. 95 (2019): 14311–14. http://dx.doi.org/10.1039/c9cc07036b.

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Enantioselective Pd-catalyzed diarylation of unactivated alkenes between arenediazonium salts and arylboronic acids has been developed. This method provides an efficient route to dihydrobenzofurans with all-carbon quaternary centers in good yields with 88–99% ee.

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24

Koziakov, Denis, Guojiao Wu, and Axel Jacobi von Wangelin. "Aromatic substitutions of arenediazonium salts via metal catalysis, single electron transfer, and weak base mediation." Organic & Biomolecular Chemistry 16, no. 27 (2018): 4942–53. http://dx.doi.org/10.1039/c8ob00591e.

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Radical aromatic substitutions of arenediazonium salts can be initiated by various methods. The recent developments of weak base-mediated protocols provide great advantages over conventional metal-mediated or photoredox reactions by their operational simplicity, price, hazard potential and scalability.

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25

BILA, Evgenia, Daryna SOLTYS, and Mykola OBUSHAK. "THREE-COMPONENT REACTIONS OF UNSATURATED COMPOUNDS WITH ARENEDIASONIUM SALTS AND NEUTRAL NUCLEOPHILS. ARYLSULFONYLATION." Proceedings of the Shevchenko Scientific Society. Series Сhemical Sciences 2020, no. 60 (2020): 31–54. http://dx.doi.org/10.37827/ntsh.chem.2020.60.031.

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The results of recent achievements on the interaction of arenediazonium salts with unsaturated compounds in the presence of neutral nucleophiles are summarized. New examples of multicomponent transformations with the participation of such neutral nucleophiles as CO (arylcarbonylation), NO (arylnitrosylation), aceto¬nitrile (aminoarylation), SO2 (arylsulfonylation) and others are given. These reactions can be applied to alkenes, alkynes, aromatic compounds. Mild reaction conditions allow the use of reagents with different functional groups. Reactions of this type open up the possibility of one-

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26

Doyle, Michael P., Judith K. Guy, Kathlynn C. Brown, Surendra N. Mahapatro, Craig M. VanZyl, and Jack R. Pladziewicz. "Outer-sphere one-electron reductions of arenediazonium salts." Journal of the American Chemical Society 109, no. 5 (1987): 1536–40. http://dx.doi.org/10.1021/ja00239a038.

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27

Salabert, Jordi, Rosa María Sebastián, Adelina Vallribera, José Francisco Cívicos, and Carmen Nájera. "Heck–Matsuda reaction of arenediazonium salts in water." Tetrahedron 69, no. 12 (2013): 2655–59. http://dx.doi.org/10.1016/j.tet.2013.01.049.

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28

Collins, Gillian, Peter Fleming, Colm O’Dwyer, Michael A. Morris, and Justin D. Holmes. "Organic Functionalization of Germanium Nanowires using Arenediazonium Salts." Chemistry of Materials 23, no. 7 (2011): 1883–91. http://dx.doi.org/10.1021/cm103573m.

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29

Matheis, Christian, Kevin Jouvin, and Lukas J. Goossen. "ChemInform Abstract: Sandmeyer Difluoromethylation of (Hetero-)Arenediazonium Salts." ChemInform 46, no. 18 (2015): no. http://dx.doi.org/10.1002/chin.201518078.

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30

KOIZUMI, T., N. BASHIR, and J. A. MURPHY. "ChemInform Abstract: Reactions of Arenediazonium Salts with Diazadithiafulvalenes." ChemInform 29, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.199805121.

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31

LAMPARD, C., J. A. MURPHY, F. RASHEED, N. LEWIS, M. B. HURSTHOUSE, and D. E. HIBBS. "ChemInform Abstract: Novel Synthetic Applications of Arenediazonium Salts." ChemInform 26, no. 16 (1995): no. http://dx.doi.org/10.1002/chin.199516046.

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32

Fabrizi, Giancarlo, Antonella Goggiamani, Alessio Sferrazza, and Sandro Cacchi. "ChemInform Abstract: Sonogashira Cross-Coupling of Arenediazonium Salts." ChemInform 41, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.201040084.

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33

Hata, Dai, Mamoru Tobisu, and Toru Amaya. "Electrolytic Cross-Coupling of Arenediazonium Salts and Heteroarenes." Bulletin of the Chemical Society of Japan 91, no. 12 (2018): 1749–51. http://dx.doi.org/10.1246/bcsj.20180193.

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34

Cacchi, Sandro, Giancarlo Fabrizi, Antonella Goggiamani, and Daniela Persiani. "Palladium-Catalyzed Hydroarylation of Alkynes with Arenediazonium Salts." Organic Letters 10, no. 8 (2008): 1597–600. http://dx.doi.org/10.1021/ol800266e.

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35

Bertoli, Giulia, Benjamin Exner, Mathies V. Evers, Kristina Tschulik, and Lukas J. Gooßen. "Metal-free trifluoromethylthiolation of arenediazonium salts with Me4NSCF3." Journal of Fluorine Chemistry 210 (June 2018): 132–36. http://dx.doi.org/10.1016/j.jfluchem.2018.03.011.

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36

Kutonova, Ksenia V., Marina E. Trusova, Andrey V. Stankevich, Pavel S. Postnikov, and Victor D. Filimonov. "Matsuda–Heck reaction with arenediazonium tosylates in water." Beilstein Journal of Organic Chemistry 11 (March 16, 2015): 358–62. http://dx.doi.org/10.3762/bjoc.11.41.

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An environmentally friendly Matsuda–Heck reaction with arenediazonium tosylates has been developed for the first time. A range of alkenes was arylated in good to quantitative yields in water. The reaction is significantly accelerated when carried out under microwave heating. The arylation of haloalkylacrylates with diazonium salts has been implemented for the first time.

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37

Beckwith, ALJ, RA Jackson, and RW Longmore. "The Intermediacy of Free Aryl Radicals in the Reaction of o-Alkenyloxybenzenediazonium Salts With Ferrocene." Australian Journal of Chemistry 45, no. 5 (1992): 857. http://dx.doi.org/10.1071/ch9920857.

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The formation of 3-ferrocenylmethyl-2,3-dihydrobenzofuran (5a) and similar products bearing cyclized substituents, when ferrocene or mixtures of ferrocene and ferrocenium ion are treated witho - allyloxybenzene - or o-but-3-enyloxybenzene-dimonium salts, provides unequivocal evidence for the intermediacy of free aryl radicals in the reaction of ferrocene with arenediazonium salts. The results are consistent with a mechanism involving electron transfer and dediazoniation followed by homolytic attack on ferroce nium ion.

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38

Chuprun, Sergey, Dmitry Dar’in, Grigory Kantin та Mikhail Krasavin. "[3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles". Synthesis 51, № 21 (2019): 3998–4005. http://dx.doi.org/10.1055/s-0039-1690159.

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[3+2]-Cycloaddition of arenediazonium salts with diazo compounds (earlier exemplified only for trimethylsilyldiazomethane and 2,2,2-trifluorodiazoethane) has been developed to include a wide range of readily available α-diazocarbonyl compounds. The resulting 2-aryl-5-acyl-2H-tetrazoles are of high value in medicinal chemistry.

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39

Kharissova, Oxana V., H. Leija, and E. G. de Casas-Ortiz. "Functionalization of carbon nanotubes with arenedyazonium salts in urea." MRS Proceedings 1451 (2012): 103–10. http://dx.doi.org/10.1557/opl.2012.1336.

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ABSTRACTThe functionalization of single wall carbon nanotubes (SWCNT) with arenediazonium salts, formed in situ from anilines as dimethyl-5-aminoisophthalate, sulfanilamide and p-anisidine, using the environmentally solvent urea. The functionalized SWNTs were then characterized using spectroscopic and microscopic methods along with thermogravimetric analysis (TGA). According to enhance solubility in solvents after that introduce them into the industrial processes. The molecules added appear on the nanotubes like chemical anchors.

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40

Naveen, Naganaboina, Saumitra Sengupta, and Srinivasan Chandrasekaran. "Metal-Free S-Arylation of Cysteine Using Arenediazonium Salts." Journal of Organic Chemistry 83, no. 7 (2018): 3562–69. http://dx.doi.org/10.1021/acs.joc.7b03160.

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41

Zheng, Changge, Yang Liu, Jianquan Hong, et al. "Copper(I)-promoted trifluoromethylthiolation of arenediazonium salts with AgSCF3." Tetrahedron Letters 60, no. 21 (2019): 1404–7. http://dx.doi.org/10.1016/j.tetlet.2019.04.018.

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42

Huang, Liangbin, Dagmar Hackenberger, and Lukas J. Gooßen. "Iridium-Catalyzedortho-Arylation of Benzoic Acids with Arenediazonium Salts." Angewandte Chemie International Edition 54, no. 43 (2015): 12607–11. http://dx.doi.org/10.1002/anie.201505769.

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43

Ambroz, Hanna B., Keith R. Jennings, and Terence J. Kemp. "Mass spectrometry of arenediazonium salts by fast atom bombardment." Organic Mass Spectrometry 23, no. 8 (1988): 605–8. http://dx.doi.org/10.1002/oms.1210230810.

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44

Wu, Wei, Qinli Tian, Taotao Chen, and Zhiqiang Weng. "Copper-Mediated Trifluoroacetylation of Arenediazonium Salts with Ethyl Trifluoropyruvate." Chemistry - A European Journal 22, no. 46 (2016): 16455–58. http://dx.doi.org/10.1002/chem.201604300.

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45

Hata, Dai, Toshiyuki Moriuchi, Toshikazu Hirao, and Toru Amaya. "Polyaniline-Induced Arylation with Arenediazonium Salts Derived from Anilines." Chemistry - A European Journal 23, no. 32 (2017): 7703–9. http://dx.doi.org/10.1002/chem.201700630.

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46

SUGIMOTO, T., and W. PFLEIDERER. "ChemInform Abstract: Arylation of 1,3-Dimethyllumazines by Arenediazonium Salts." ChemInform 28, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199741200.

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47

Churkina, L. N., E. Yu Belyaev, and E. M. Lopatina. "ChemInform Abstract: Reactions of Benzamide Oximes with Arenediazonium Salts." ChemInform 32, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.200135081.

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48

Pratsch, Gerald, Christian A. Anger, Katharina Ritter, and Markus R. Heinrich. "ChemInform Abstract: Hydroxy- and Aminophenyl Radicals from Arenediazonium Salts." ChemInform 42, no. 33 (2011): no. http://dx.doi.org/10.1002/chin.201133035.

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49

Liu, Yongan, Donghai Yu, Yong Guo, Ji-Chang Xiao, Qing-Yun Chen, and Chao Liu. "Arenesulfonyl Fluoride Synthesis via Copper-Catalyzed Fluorosulfonylation of Arenediazonium Salts." Organic Letters 22, no. 6 (2020): 2281–86. http://dx.doi.org/10.1021/acs.orglett.0c00484.

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50

Trusova, Marina E., Ksenia V. Kutonova, Victor V. Kurtukov, Victor D. Filimonov, and Pavel S. Postnikov. "Arenediazonium salts transformations in water media: Coming round to origins." Resource-Efficient Technologies 2, no. 1 (2016): 36–42. http://dx.doi.org/10.1016/j.reffit.2016.01.001.

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