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Journal articles on the topic 'Haloarens'

Author: Grafiati

Published: 5 June 2025

Last updated: 2 August 2025

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1

Nocera, Giuseppe, and John A. Murphy. "Ground State Cross-Coupling of Haloarenes with Arenes Initiated by Organic Electron Donors, Formed in situ: An Overview." Synthesis 52, no. 03 (2019): 327–36. http://dx.doi.org/10.1055/s-0039-1690614.

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Many reactions have been discovered that lead to coupling of haloarenes to arenes using potassium tert-butoxide as the base, and one of a variety of organic compounds as an additive. The organic additive reacts with the base to form a strong organic electron donor in situ that initiates a base-induced homolytic aromatic substitution (BHAS) coupling reaction, by converting the haloarene into an aryl radical. This brief report presents an overview of the wide range of organic additives that can be used, and the organic electron donors that they form.

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2

Saberov, Vagiz Sh, Daniel A. Evans, Nikolai I. Korotkikh, et al. "Exceptionally efficient catalytic hydrodechlorination of persistent organic pollutants: application of new sterically shielded palladium carbene complexes." Dalton Trans. 43, no. 48 (2014): 18117–22. http://dx.doi.org/10.1039/c4dt02908a.

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3

Nozawa-Kumada, Kanako, Yuki Iwakawa, So Onuma, Masanori Shigeno, and Yoshinori Kondo. "NaH-mediated direct C–H arylation in the presence of 1,10-phenanthroline." Chemical Communications 56, no. 56 (2020): 7773–76. http://dx.doi.org/10.1039/d0cc00730g.

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4

Del Grosso, Alessandro, Josue Ayuso Carrillo, and Michael J. Ingleson. "Regioselective electrophilic borylation of haloarenes." Chemical Communications 51, no. 14 (2015): 2878–81. http://dx.doi.org/10.1039/c4cc10153g.

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5

Bzeih, Tourin, Timothée Naret, Ali Hachem, et al. "A general synthesis of arylindoles and (1-arylvinyl)carbazoles via a one-pot reaction from N-tosylhydrazones and 2-nitro-haloarenes and their potential application to colon cancer." Chemical Communications 52, no. 88 (2016): 13027–30. http://dx.doi.org/10.1039/c6cc07666a.

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6

Konishi, Hideyuki, Hiroki Nagase, and Kei Manabe. "Concise synthesis of cyclic carbonyl compounds from haloarenes using phenyl formate as the carbonyl source." Chemical Communications 51, no. 10 (2015): 1854–57. http://dx.doi.org/10.1039/c4cc09413a.

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7

Hassan, Mohamed E. "Palladium catalyzed coupling reaction for the synthesis of C-5 aryl and heteroaryl substituted 2’-deoxycytidine." Collection of Czechoslovak Chemical Communications 56, no. 6 (1991): 1295–99. http://dx.doi.org/10.1135/cccc19911295.

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Cytosine nucleosides substituted at C-5 with differently substituted aryls and heteroaryls have been prepared via a palladium catalyzed reaction utilizing 5-chloromercuri or acetoxymercuri nucleosides and haloarenes or heteroarenes.

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8

Mahmood, Qaiser, Erlin Yue, Wenjuan Zhang, Gregory A. Solan, Tongling Liang, and Wen-Hua Sun. "Bisimino-functionalized dibenzo[a,c]acridines as highly conjugated pincer frameworks for palladium(ii): synthesis, characterization and catalytic performance in Heck coupling." Organic Chemistry Frontiers 3, no. 12 (2016): 1668–79. http://dx.doi.org/10.1039/c6qo00469e.

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The NNC-Pd pincer complexes, systematically derived from phenanthrene-9,10-dione, are able to efficiently mediate the coupling of haloarenes with vinyl-containing substrates (up to TON = 174 000) with a broad substrate scope.

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9

Favier, Isabelle, Marie-Lou Toro, Pierre Lecante, Daniel Pla, and Montserrat Gómez. "Palladium-mediated radical homocoupling reactions: a surface catalytic insight." Catalysis Science & Technology 8, no. 18 (2018): 4766–73. http://dx.doi.org/10.1039/c8cy00901e.

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In this work, we report a palladium nanoparticle-promoted reductive homocoupling of haloarenes, exhibiting a broad functional group tolerance. A mechanistic study was carried out, suggesting single-electron transfer processes on the metal surface.

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10

Emery, Katie J., Tell Tuttle, and John A. Murphy. "Evidence of single electron transfer from the enolate anion of an N,N′-dialkyldiketopiperazine additive in BHAS coupling reactions." Org. Biomol. Chem. 15, no. 41 (2017): 8810–19. http://dx.doi.org/10.1039/c7ob02209c.

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A designed N,N′-dialkyldiketopiperazine (DKP) provides evidence for the role of DKP additives as initiators that act by electron transfer in base-induced homolytic aromatic substitution reactions, involving coupling of haloarenes to arenes.

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11

Panda, Subhalaxmi, Santosh Kumar Sahu, Pradyota Kumar Behera, Reba Panigrahi, Bamakanta Garnaik, and Laxmidhar Rout. "Bimetallic BaMoO4 nanoparticles for the C–S cross-coupling of thiols with haloarenes." New Journal of Chemistry 44, no. 6 (2020): 2500–2504. http://dx.doi.org/10.1039/c9nj05581a.

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The C–S cross-coupling of alkyl/aryl thiols with haloarenes using BaMoO<sub>4</sub> nanoparticles was accomplished with high yields, and good functional group tolerance and selectivity. Unactivated bromo and 4-acetyl fluoroarenes can afford thioethers in high yields.

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12

Hirai, Yoshinori, and Yasuhiro Uozumi. "Preparation of Aryl(dicyclohexyl)phosphines by C–P Bond-Forming Cross-Coupling in Water Catalyzed by an Amphiphilic-Resin-Supported Palladium Complex." Synlett 28, no. 20 (2017): 2966–70. http://dx.doi.org/10.1055/s-0036-1590926.

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Aryl(dicyclohexyl)phosphines were prepared by a catalytic C–P bond-forming cross-coupling reaction of haloarenes with dicyclohexylphosphine under heterogeneous conditions in water containing an immobilized palladium complex coordinated to an amphiphilic polystyrene–poly(ethylene glycol) resin supported di(tert-butyl)phosphine ligand.

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13

Baik, Woonphil, Wanqiang Luan, Hyun Joo Lee, Cheol Hun Yoon, Sangho Koo, and Byeong Hyo Kim. "Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ." Canadian Journal of Chemistry 83, no. 3 (2005): 213–19. http://dx.doi.org/10.1139/v05-026.

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Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic

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14

More, Dipak S., Dr Pushpendra Sharma, and Dr Neelu Jain. "Green Innovative Synthesis of Chlorofluoroarenes from Nitrohaloarenes." INTERANTIONAL JOURNAL OF SCIENTIFIC RESEARCH IN ENGINEERING AND MANAGEMENT 07, no. 12 (2023): 1–9. http://dx.doi.org/10.55041/ijsrem27801.

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A new series of Haloarenes is synthesized by the de-nitrochlorination of difluoronitrobenze with dichlorobenzene as solvent without presence of catalyst. The synthesized compounds have been characterized by boiling point, elemental analysis, MS, one-dimensional NMR (1H & 13C) spectroscopic data. -------------------------------------------------------------------------------------------------------------------------------------------------------- Keywords: Nitrofluoroarenes, De-nitrochloroination, NMR, Mass Spectroscopy etc.

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15

SUCHITRA, DWIVEDI, SINGH MANORAMA, and ACHAL MISRA RAM. "Reaction of Organohalogens with in situ Electrogenerated Superoxide Ion." Journal of Indian Chemical Society Vol. 72, Jan 1995 (1995): 37–39. https://doi.org/10.5281/zenodo.5900455.

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Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi-221 005 <em>Manuscript received 26 May 1993, revised 4 August 1993, accepted 12 October 1993</em> Superoxide ion, generated by electrochemical reduction of 02 in dimethylformamide at mercury cathode, reacts as an effective nucleophile with haloarenes (1a-4a) and as a base with phenacyl halides (5a and 6a) affording phenols (la-4b) and <em>trans</em>-dibenzoylethene (5b) respectively.

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16

Buchwald, S., and A. Shafir. "A Mild Copper-Catalyzed Amination of Haloarenes." Synfacts 2006, no. 10 (2006): 1055. http://dx.doi.org/10.1055/s-2006-949307.

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17

Brenda, Martin, Arno Knebelkamp, Andreas Greiner, and Walter Heitz. "Novel Palladium-Catalyzed Biaryl Synthesis with Haloarenes." Synlett 1991, no. 11 (1991): 809–10. http://dx.doi.org/10.1055/s-1991-20885.

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18

Vlasova, N. N., L. I. Belousova, A. V. Vlasov, T. I. Vakul’skaya, S. S. Khutsishvili, and M. G. Voronkov. "Photochemical reactions of acyl iodides with haloarenes." Doklady Chemistry 438, no. 2 (2011): 164–66. http://dx.doi.org/10.1134/s0012500811060048.

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19

Del Grosso, Alessandro, Josue Ayuso Carrillo, and Michael J. Ingleson. "ChemInform Abstract: Regioselective Electrophilic Borylation of Haloarenes." ChemInform 46, no. 27 (2015): no. http://dx.doi.org/10.1002/chin.201527234.

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20

Senoo, Takahiro, Aiko Inoue та Keiji Mori. "Facile Synthesis of π-Conjugated Heteroaromatic Compounds via Weak-Base-Promoted Transition-Metal-Free C–N Coupling". Synthesis 52, № 07 (2020): 1096–102. http://dx.doi.org/10.1055/s-0039-1690788.

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A K2CO3-promoted transition-metal-free C–N coupling reaction was developed. When a solution of 1-(2-aminophenyl)-8-iodonaphthalenes in DMSO was treated with 2.5 equivalents of K2CO3 and 5.0 equivalents of MeI, intramolecular C–N coupling reaction proceeded smoothly even at low temperature (room temperature) to afford various heteroaromatic compounds in good chemical yields. Additional experiments suggested that this reaction might have proceeded through an unusual SNAr reaction between haloarenes and a bulky tertiary amine moiety.

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21

Gao, Cai-Yan, Xingbo Cao, and Lian-Ming Yang. "Nickel-catalyzed cross-coupling of diarylamines with haloarenes." Organic & Biomolecular Chemistry 7, no. 19 (2009): 3922. http://dx.doi.org/10.1039/b911286c.

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22

Mfuh, Adelphe M., Brett D. Schneider, Westley Cruces, and Oleg V. Larionov. "Metal- and additive-free photoinduced borylation of haloarenes." Nature Protocols 12, no. 3 (2017): 604–10. http://dx.doi.org/10.1038/nprot.2016.184.

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23

Cantrell, William R., William E. Bauta, and Tracy Engles. "Hydrogen peroxide promoted hydroxylation of haloarenes and heteroarenes." Tetrahedron Letters 47, no. 25 (2006): 4249–51. http://dx.doi.org/10.1016/j.tetlet.2006.04.020.

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24

Sedishev, I. P., N. E. Agafonov, A. A. Kutin, and V. M. Zhulin. "Haloarenes in the Duff reaction under high pressures." Russian Chemical Bulletin 44, no. 11 (1995): 2127–30. http://dx.doi.org/10.1007/bf00696718.

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25

Dahlmann, Uwe, and K. Peter C. Vollhardt. "Oligoether-Substituted Derivatives of Carbon-Rich 1,4,7,10,13,16-Hexaethynyltribenzo[a,e,i]cyclododeca-5,11,17-triyne (C36H12) and 1,4,9,12-Tetrakis(ethynyl)dibenzo[a,g]cyclododeca-5,7,13,15-tetrayne (C28H8): Potential Precursors to the Circular [6]Phenylene (‘Antikekulene’) Frame." Synthesis 52, no. 08 (2020): 1287–300. http://dx.doi.org/10.1055/s-0039-1690050.

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The title compounds, in which the terminal alkyne functions are adorned with -CH2OCH2CH2OCH2CH2OCH2CH3 or -p-C6H4OCH2CH2 OCH2CH2OCH3 substituents, were synthesized. The strategies for their preparation relied on prior art and involved the use of Sonogashira alkynylations of appropriate haloarenes, Stephens–Castro cyclizations of 1,2,4-trialkynyl-3-iodobenzenes, and Hay oxidative couplings of 1,2,3,4-tetralkynylbenzenes. The targets form yellow materials, exhibiting yellow-green fluorescence, and they are very soluble in polar solvents, but only sparingly so in nonpolar media. Attempts to conve

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26

Abudken, Ahmed M. H., and Duaa Q. Kamil. "Cu-Catalyzed Halogenation of Diaryliodonium Salts Containing Ortho-sidearm." International Academic Journal of Science and Engineering 11, no. 1 (2024): 65–70. http://dx.doi.org/10.9756/iajse/v11i1/iajse1109.

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A simple and efficient halogenation pathway has been delivered with various diaryliodonium salts, containing an ortho alcoholic sidearm, and CuCl or CuBr to produce chloroarenes and bromoarenes in para position only without any ortho aromatic isomer. The reaction conditions include temperature (60 oC), solvent (DMF) and reaction time (2 hours) were optimized in order to obtain high yields of products. All products were isolated and characterized via 1H-NMR and 13C-NMR. With further investigation, these methods could be the main entrance to prepare herbicides, insecticides and bactericides cont

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27

Studzinskii, O. P., L. M. Borisova, and R. P. Ponomareva. "Photolysis of Optical Whiteners in the Presence of Haloarenes." Russian Journal of General Chemistry 73, no. 11 (2003): 1803–5. http://dx.doi.org/10.1023/b:rugc.0000018659.33367.b0.

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28

Monopoli, A., A. Nacci, V. Calò, et al. "Reductive Homocoupling of Haloarenes in Water with Palladium Nanoparticles." Synfacts 2010, no. 09 (2010): 1083. http://dx.doi.org/10.1055/s-0030-1257983.

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29

Henly, Timothy J., Carolyn B. Knobler, and M. Frederick Hawthorne. "Reactions of anionic carborane nucleophiles with chromium-coordinated haloarenes." Organometallics 11, no. 6 (1992): 2313–16. http://dx.doi.org/10.1021/om00042a057.

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30

Keane, Mark A. "Hydrodehalogenation of haloarenes over Silica supported Pd and Ni." Applied Catalysis A: General 271, no. 1-2 (2004): 109–18. http://dx.doi.org/10.1016/j.apcata.2004.02.051.

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31

Ong, Derek Yiren, Ciputra Tejo, Kai Xu, Hajime Hirao, and Shunsuke Chiba. "Hydrodehalogenation of Haloarenes by a Sodium Hydride-Iodide Composite." Angewandte Chemie International Edition 56, no. 7 (2017): 1840–44. http://dx.doi.org/10.1002/anie.201611495.

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32

BRENDA, M., A. KNEBELKAMP, A. GREINER, and W. HEITZ. "ChemInform Abstract: Novel Palladium-Catalyzed Biaryl Synthesis with Haloarenes." ChemInform 23, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199220135.

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33

Ong, Derek Yiren, Ciputra Tejo, Kai Xu, Hajime Hirao, and Shunsuke Chiba. "Hydrodehalogenation of Haloarenes by a Sodium Hydride-Iodide Composite." Angewandte Chemie 129, no. 7 (2017): 1866–70. http://dx.doi.org/10.1002/ange.201611495.

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34

PARK, Y. T., Y. H. KIM, C. G. HWANG, and D. D. SUNG. "ChemInform Abstract: Photochemical Reactivities of Benzenes Tethered to Haloarene." ChemInform 27, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199646055.

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35

Schulte, Robin, and Heiko Ihmels. "Borylated norbornadiene derivatives: Synthesis and application in Pd-catalyzed Suzuki–Miyaura coupling reactions." Beilstein Journal of Organic Chemistry 18 (April 1, 2022): 368–73. http://dx.doi.org/10.3762/bjoc.18.41.

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The photochromic norbornadiene/quadricyclane system is among the most promising candidates for molecular solar thermal (MOST) energy storage. As in this context there is still the need for new tailor-made derivatives, borylated norbornadienes were synthesized that may be used as versatile building blocks. Thus, the 4,4,5,5-tetramethyl-2-(bicyclo[2.2.1]heptadien-2-yl)-1,3,2-dioxaborolane was prepared and shown to be a suitable substrate for Pd-catalyzed Suzuki–Miyaura coupling reactions with selected haloarenes. It was demonstrated exemplarily that the novel monosubstituted 2-(1-naphthyl)norbor

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36

Moursounidis, John, and Dieter Wege. "Benzannulated Isobenzofurans." Australian Journal of Chemistry 41, no. 2 (1988): 235. http://dx.doi.org/10.1071/ch9880235.

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A number of arynes, generated by treatment of haloarenes with sodium or potassium amide in tetrahydrofuran, were trapped with furan. The resulting dihydro epoxy arenes were converted into the following annulated isobenzofuran derivatives by using reverse Diels-Alder methodology: naphtho[l,2-clfuran, phenanthro[9,10-elfuran, pyreno[l,2-elfuran, pyreno[3,4- elfuran, anthra[l,2- elfuran, phenanthro[l,2- clfuran and phenanthro[3,4- elfuran. Bimolecular rate constants for the addition of maleic anhydride to these furans were measured, and were correlated with the Herndon structure count. Addition o

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37

Le, Chip, Tiffany Q. Chen, Tao Liang, Patricia Zhang, and David W. C. MacMillan. "A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes." Science 360, no. 6392 (2018): 1010–14. http://dx.doi.org/10.1126/science.aat4133.

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Transition metal–catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a wide variety of coupling fragments. However, the sluggish nature of oxidative addition has limited copper’s capacity to broadly facilitate haloarene coupling protocols. Here, we demonstrate that this copper oxidative addition problem can be overcome with an aryl radical–capture mechanism, wherein the aryl radical is

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38

Saberov, Vagiz, Alexander Avksentiev, Gennady Rayenko, et al. "CATALYSIS OF HYDRODEHALOGENATION REACTION OF HALOARENES BY CARBENE PEPPSI-PALLADIUM COMPLEXES." Ukrainian Chemistry Journal 88, no. 1 (2022): 67–81. http://dx.doi.org/10.33609/2708-129x.88.01.2022.67-81.

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The synthesis of a number of carbene PEPPSI-complexes of palladium with various pyridine and carbene ligands was carried out by reactions of 1,3-bis-(2,6-dibenzhydryl-4-methylphenyl)imidazolium chloride IPr*.HCl [compounds 7a-c IPr*PdCl2L’, L’ = pyridine (а), 3-chloropyridine (b), 4-dimethylaminopyridine (с)], 1,3-bis-(2,6-diisopropylphenyl)imidazolium perchlorate IPr.HClO4 [compounds 8a,b IPr.PdCl2L’, L’ = 3-chloropyridine (а), о-phenanthroline (b)], 1,3-diphenyl-4-(2,6-diisopropylphenyl)-1,2,4-triazolium perchlorate L.HClO4 (complex 9 LPdCl2L’, L’ = 3-chloropyridine) and 1,3-dicetylimi

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39

Lin, Yi-Ching, Ko-Wang Yen, Hsuan-Jen Lin, Yi-Chi Yang, and Yen-Ku Wu. "Haloarene-guided cascade arylation of cyclic vinylogous esters under palladium catalysis." Chemical Communications 57, no. 91 (2021): 12119–22. http://dx.doi.org/10.1039/d1cc05006k.

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40

Mečiarová, Mária, Štefan Toma, and Peter Magdolen. "Ultrasound effect on the aromatic nucleophilic substitution reactions on some haloarenes." Ultrasonics Sonochemistry 10, no. 4-5 (2003): 265–70. http://dx.doi.org/10.1016/s1350-4177(02)00157-8.

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41

Keane, Mark A., and Ragnar Larsson. "Isokinetic behaviour in gas phase catalytic haloarene hydrodehalogenation reactions: Mechanistic considerations." Journal of Molecular Catalysis A: Chemical 249, no. 1-2 (2006): 158–65. http://dx.doi.org/10.1016/j.molcata.2006.01.017.

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42

Shida, Naoki, Shohei Yoshinaga та Mahito Atobe. "Electrochemical C-N Coupling Reaction Mediated by π-Extended Haloarene Catalyst". ECS Meeting Abstracts MA2023-01, № 41 (2023): 2324. http://dx.doi.org/10.1149/ma2023-01412324mtgabs.

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Hypervalent iodine is a useful reagent in synthetic organic chemistry,[1] but because these reagents are synthesized by reaction with stoichiometric amounts of oxidants, their large-scale use is associated with safety and environmental impact concerns. Hypervalent iodine can also be synthesized by electrochemical oxidation of the corresponding iodoarenes, and the electrochemically generated hypervalent iodine can be immediately reacted and used catalytically, i.e., as an electrochemical mediator, to enable a reaction system that is safe and generates little waste.[2] The use of hypervalent iod

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43

Ben-Ari, Eyal, Mark Gandelman, Haim Rozenberg, Linda J. W. Shimon, and David Milstein. "Selective Ortho C−H Activation of Haloarenes by an Ir(I) System." Journal of the American Chemical Society 125, no. 16 (2003): 4714–15. http://dx.doi.org/10.1021/ja028362p.

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44

Simonetti, Marco, Rositha Kuniyil, Stuart A. Macgregor, and Igor Larrosa. "Benzoate Cyclometalation Enables Oxidative Addition of Haloarenes at a Ru(II) Center." Journal of the American Chemical Society 140, no. 37 (2018): 11836–47. http://dx.doi.org/10.1021/jacs.8b08150.

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45

Nazareno, Mónica A., and Roberto A. Rossi. "SmI2 catalyzed SRN1 reactions of haloarenes with acetophenone enolate ions in DMSO." Tetrahedron Letters 35, no. 29 (1994): 5185–88. http://dx.doi.org/10.1016/s0040-4039(00)77059-6.

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46

Maestri, Giovanni, Tatiana Cañeque, Nicola Della Ca’, et al. "Pd Catalysis in Cyanide-Free Synthesis of Nitriles from Haloarenes via Isoxazolines." Organic Letters 18, no. 23 (2016): 6108–11. http://dx.doi.org/10.1021/acs.orglett.6b03103.

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47

Fier, Patrick S., and Kevin M. Maloney. "Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions." Organic Letters 18, no. 9 (2016): 2244–47. http://dx.doi.org/10.1021/acs.orglett.6b00876.

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48

Linnert, Harrald V., and José M. Riveros. "Benzyne-related mechanisms in the gas phase ion/molecule reactions of haloarenes." International Journal of Mass Spectrometry and Ion Processes 140, no. 1 (1994): 163–76. http://dx.doi.org/10.1016/0168-1176(94)04079-6.

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49

Allen, C. C. R., C. J. Boudet, C. Hardacre, and M. E. Migaud. "Enhancement of whole cell dioxygenase biotransformations of haloarenes by toxic ionic liquids." RSC Adv. 4, no. 38 (2014): 19916–24. http://dx.doi.org/10.1039/c4ra00640b.

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50

Gorecka, Joanna, Christophe Heiss, Rosario Scopelliti, and Manfred Schlosser. "Buttressing Effects on Haloarene Deprotonation: A Merely Kinetic or Also Thermodynamic Phenomenon?" Organic Letters 6, no. 24 (2004): 4591–93. http://dx.doi.org/10.1021/ol0480022.

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