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Journal articles on the topic 'Diaryliodonium salt'

Author: Grafiati

Published: 30 November 2024

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1

Corrie, Tom J. A., and Guy C. Lloyd-Jones. "Formal Synthesis of (±)-Allocolchicine Via Gold-Catalysed Direct Arylation: Implication of Aryl Iodine(III) Oxidant in Catalyst Deactivation Pathways." Topics in Catalysis 60, no. 8 (April 19, 2017): 570–79. http://dx.doi.org/10.1007/s11244-017-0742-z.

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Abstract A concise formal synthesis of racemic allocolchicine has been developed, centred on three principal transformations: a retro-Brook alkylation reaction to generate an arylsilane, a gold-catalysed arylative cyclisation to generate the B-ring via biaryl linkage, and a palladium-catalysed carbonylation of an aryl chloride to generate an ester. 1H NMR monitoring of the key gold-catalysed cyclisation step reveals that a powerful catalyst deactivation process progressively attenuates the rate of catalyst turnover. The origins of the catalyst deactivation have been investigated, with an uncatalysed side-reaction, involving the substrate and the iodine(III) oxidant, identified as the source of a potent catalyst poison. The side reaction generates 1–4% of a diaryliodonium salt, and whilst this moiety is shown not to be an innate catalyst deactivator, when it is tethered to the arylsilane reactant, the inhibition becomes powerful. Kinetic modelling of processes run at two different catalyst concentrations allows extraction of the partitioning of the gold catalyst between the substrate and its diaryliodonium salt, with a rate of diaryliodonium salt generation consistent with that independently determined in the absence of catalyst. The high partition ratio between substrate and diaryliodonium salt (5/1) results in very efficient, and ultimately complete, diversion of the catalyst off-cycle. Graphical Abstract

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2

Chen, Yu, Xiaoqin Jia, Mengqiang Wang, and Tao Wang. "A synergistic effect of a ferrocenium salt on the diaryliodonium salt-induced visible-light curing of bisphenol-A epoxy resin." RSC Advances 5, no. 42 (2015): 33171–76. http://dx.doi.org/10.1039/c4ra16077k.

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3

Crivello, J. V., and J. L. Lee. "Alkoxy-substituted diaryliodonium salt cationic photoinitiators." Journal of Polymer Science Part A: Polymer Chemistry 27, no. 12 (November 1989): 3951–68. http://dx.doi.org/10.1002/pola.1989.080271207.

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4

Wang, Ming, Jianpeng Wei, Qiaoling Fan, and Xuefeng Jiang. "Cu(ii)-catalyzed sulfide construction: both aryl groups utilization of intermolecular and intramolecular diaryliodonium salt." Chemical Communications 53, no. 20 (2017): 2918–21. http://dx.doi.org/10.1039/c6cc09201b.

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5

Xia, Xiao-Feng, Guo-Wei Zhang, An-Xi Zhou, and Wei He. "Copper-Catalyzed Base-Free N-Arylation of 8-Aminoquinoline Amides through Chelation Assistance." Synlett 29, no. 17 (September 11, 2018): 2269–74. http://dx.doi.org/10.1055/s-0037-1610906.

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A new and efficient approach for the N-arylation of 8-aminoquinoline amides with diaryliodonium salts has been developed. This chelation-assisted selective C–N cross-coupling reaction gave the desired N-arylated 8-aminoquinoline in moderate to good yields. In contrast to previous reports, no additional ligands and bases are used in this transformation. In addition, the anion of the diaryliodonium salt plays an important role in the success of the process.

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6

Lin, Zhaowei, Maojian Lu, Boyi Liu, Jing Gao, Mingqiang Huang, Zhenhong Gan, and Shunyou Cai. "Oxidative alkylation of alkenes with carbonyl compounds through concomitant 1,2-aryl migration by photoredox catalysis." New Journal of Chemistry 44, no. 37 (2020): 16031–35. http://dx.doi.org/10.1039/d0nj03733h.

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7

Li, Shiqing, Hongxu Lv, Yu Yu, Xiuqing Ye, Baisong Li, Songming Yang, Yanru Mo, and Xiangfei Kong. "Domino N-/C- or N-/N-/C-arylation of imidazoles to yield polyaryl imidazolium salts via atom-economical use of diaryliodonium salts." Chemical Communications 55, no. 75 (2019): 11267–70. http://dx.doi.org/10.1039/c9cc05237b.

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A Cu-mediated domino di-/triarylation reaction of imidazoles in a single step by using two aryls as well as an anion of a diaryliodonium salt is developed to quickly achieve polyaryl imidazolium salts.

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8

Das, Prajwalita, Etsuko Tokunaga, Hidehiko Akiyama, Hiroki Doi, Norimichi Saito, and Norio Shibata. "Synthesis of fluoro-functionalized diaryl-λ3-iodonium salts and their cytotoxicity against human lymphoma U937 cells." Beilstein Journal of Organic Chemistry 14 (February 7, 2018): 364–72. http://dx.doi.org/10.3762/bjoc.14.24.

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Conscious of the potential bioactivity of fluorine, an investigation was conducted using various fluorine-containing diaryliodonium salts in order to study and compare their biological activity against human lymphoma U937 cells. Most of the compounds tested are well-known reagents for fluoro-functionalized arylation reactions in synthetic organic chemistry, but their biological properties are not fully understood. Herein, after initially investigating 18 fluoro-functionalized reagents, we discovered that the ortho-fluoro-functionalized diaryliodonium salt reagents showed remarkable cytotoxicity in vitro. These results led us to synthesize more compounds, previously unknown sterically demanding diaryliodonium salts having a pentafluorosulfanyl (SF5) functional group at the ortho-position, that is, unsymmetrical ortho-SF5 phenylaryl-λ3-iodonium salts. Newly synthesized mesityl(2-(pentafluoro-λ6-sulfanyl)phenyl)iodonium exhibited the greatest potency in vitro against U937 cells. Evaluation of the cytotoxicity of selected phenylaryl-λ3-iodonium salts against AGLCL (a normal human B cell line) was also examined.

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9

Crivello, James V., and Michael F. Aldersley. "Supramolecular diaryliodonium salt‐crown ether complexes as cationic photoinitiators." Journal of Polymer Science Part A: Polymer Chemistry 51, no. 4 (December 5, 2012): 801–14. http://dx.doi.org/10.1002/pola.26452.

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10

Reinhard, Dominik L., Anna Schmidt, Marc Sons, Julian Wolf, Elric Engelage, and Stefan M. Huber. "Evaluating the halogen bonding strength of a iodoloisoxazolium(III) salt." Beilstein Journal of Organic Chemistry 20 (September 23, 2024): 2401–7. http://dx.doi.org/10.3762/bjoc.20.204.

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Diaryliodonium(III) salts have been established as powerful halogen-bond donors in recent years. Herein, a new structural motif for this compound class was developed: iodoloisoxazolium salts, bearing a cyclic five-membered iodolium core fused with an isoxazole ring. A derivative of this class was synthesized and investigated in the solid state by X-ray crystallography. Finally, the potential as halogen-bonding activator was benchmarked in solution in the gold-catalyzed cyclization of a propargyl amide.

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11

Li, Wen-Xin, Bo-Wen Yang, Jin-He Na, Weidong Rao, Xue-Qiang Chu, and Zhi-Liang Shen. "Palladium-catalyzed cross-coupling of alkylindium reagent with diaryliodonium salt." Tetrahedron Letters 95 (April 2022): 153729. http://dx.doi.org/10.1016/j.tetlet.2022.153729.

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12

He, Yong, Wenhui Zhou, Gang Liu, Miao Zhen Li, and Erjian Wang. "Novel Visible Photosensitized Polymerization System. Squarylium Dye/Diaryliodonium Salt Combination." Journal of Photopolymer Science and Technology 13, no. 2 (2000): 253–57. http://dx.doi.org/10.2494/photopolymer.13.253.

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13

Bulut, Umut, Abidin Balan, and Cagin Caliskan. "Benzotriazole derivatives as long wavelength photosensitizers for diaryliodonium salt initiators." Journal of Polymer Science Part A: Polymer Chemistry 49, no. 3 (December 3, 2010): 729–33. http://dx.doi.org/10.1002/pola.24485.

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14

Huang, Mengen, Shujia Xu, Xunshen Wu, Min Zhao, and Limin Wang. "Synthesis, Surface Activity, and Antimicrobial Efficacy of Diaryliodonium Salt-Derived Amphiphiles." Journal of Surfactants and Detergents 21, no. 3 (April 14, 2018): 323–34. http://dx.doi.org/10.1002/jsde.12038.

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15

Zhou, Dong, Sung Hoon Kim, Wenhua Chu, Thomas Voller, and John A. Katzenellenbogen. "Evaluation of aromatic radiobromination by nucleophilic substitution using diaryliodonium salt precursors." Journal of Labelled Compounds and Radiopharmaceuticals 60, no. 9 (June 14, 2017): 450–56. http://dx.doi.org/10.1002/jlcr.3519.

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16

Kervefors, Gabriella, Antonia Becker, Chandan Dey, and Berit Olofsson. "Metal-free formal synthesis of phenoxazine." Beilstein Journal of Organic Chemistry 14 (June 20, 2018): 1491–97. http://dx.doi.org/10.3762/bjoc.14.126.

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A transition metal-free formal synthesis of phenoxazine is presented. The key step of the sequence is a high-yielding O-arylation of a phenol with an unsymmetrical diaryliodonium salt to provide an ortho-disubstituted diaryl ether. This species was cyclized to acetylphenoxazine in moderate yield. The overall yield in the three-step sequence is 72% based on recovered diaryl ether. An interesting, unusually stable iodine(III) intermediate in the O-arylation was observed by NMR and could be converted to the product upon longer reaction time.

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17

Matsumoto, Makoto, Kohei Wada, Kazuki Urakawa, and Hayato Ishikawa. "Diaryliodonium Salt-Mediated Intramolecular C–N Bond Formation Using Boron-Masking N-Hydroxyamides." Organic Letters 22, no. 3 (December 30, 2019): 781–85. http://dx.doi.org/10.1021/acs.orglett.9b04076.

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18

Maindron, Nicolas, Yoann Joyard, Guillaume Villeret, and Vincent Tadino. "Automated radiosynthesis of meta-[18F]Fluorobenzylguanidine from a diaryliodonium salt precursor on NEPTIS® module." Nuclear Medicine and Biology 108-109 (May 2022): S131. http://dx.doi.org/10.1016/s0969-8051(22)00287-6.

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19

Shibata, Kouhei, Ken-ichi Takao, and Akihiro Ogura. "Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis." Journal of Organic Chemistry 86, no. 15 (July 1, 2021): 10067–87. http://dx.doi.org/10.1021/acs.joc.1c00820.

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20

Neumann, Kiel D., Linlin Qin, Amy L. Vāvere, Bin Shen, Zheng Miao, Frederick T. Chin, Barry L. Shulkin, Scott E. Snyder, and Stephen G. DiMagno. "Efficient automated syntheses of high specific activity 6-[18F]fluorodopamine using a diaryliodonium salt precursor." Journal of Labelled Compounds and Radiopharmaceuticals 59, no. 1 (December 23, 2015): 30–34. http://dx.doi.org/10.1002/jlcr.3367.

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21

Das Adhikary, Nirmal, Subhro Mandal, Anupam Jana, and Animesh Pramanik. "Diaryliodonium salt as oxidant in sp3 C-H activation and synthesis of quinazolin-4(3H)-ones." Results in Chemistry 4 (January 2022): 100270. http://dx.doi.org/10.1016/j.rechem.2021.100270.

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22

Yang, Peng, Rui Wang, Hui Wu, Zhengyin Du, and Ying Fu. "Pd-Catalyzed C−H Arylation of Benzothiazoles with Diaryliodonium Salt: One-Pot Synthesis of 2-Arylbenzothiazoles." Asian Journal of Organic Chemistry 6, no. 2 (December 13, 2016): 184–88. http://dx.doi.org/10.1002/ajoc.201600514.

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23

Malik, Muhammad Salman, Sandra Schlögl, Markus Wolfahrt, and Marco Sangermano. "Review on UV-Induced Cationic Frontal Polymerization of Epoxy Monomers." Polymers 12, no. 9 (September 20, 2020): 2146. http://dx.doi.org/10.3390/polym12092146.

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Ultraviolet (UV)-induced cationic frontal polymerization has emerged as a novel technique that allows rapid curing of various epoxy monomers upon UV irradiation within a few seconds. In the presence of a diaryliodonium salt photoinitiator together with a thermal radical initiator, the cationic ring opening polymerization of an epoxide monomer is auto-accelerated in the form of a self-propagating front upon UV irradiation. This hot propagating front generates the required enthalpy to sustain curing reaction throughout the resin formulation without further need for UV irradiation. This unique reaction pathway makes the cationic frontal polymerization a promising route towards the efficient curing of epoxy-based thermosetting resins and related composite structures. This review represents a comprehensive overview of the mechanism and progress of UV-induced cationic frontal polymerization of epoxy monomers that have been reported so far in literature. At the same time, this review covers important aspects on the frontal polymerization of various epoxide monomers involving the chemistry of the initiators, the effect of appropriate sensitizers, diluents and fillers.

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24

Prendergast, Aisling M., Rachel Shanahan, Aobha Hickey, Francis Harrington, David Schönbauer, Peter A. Byrne, Michael Schnürch, and Gerard P. McGlacken. "Synthesis of a Diaryliodonium Salt and Its Use in the Direct Arylation of Indole: A Two-Step Experiment for the Organic Teaching Laboratory." Journal of Chemical Education 97, no. 1 (November 4, 2019): 200–206. http://dx.doi.org/10.1021/acs.jchemed.9b00525.

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25

Wang, Li, Zhen-Chu Chen, and Qin-Guo Zheng. "Hypervalent Iodine in Synthesis 64: Syntheses of Diaryl Selenides and Alkyl Aryl Selenides by Palladium-Catalyzed Arylation of Areneselenyl or Alkaneselenyl Magnesium Bromide with Diaryliodonium Salt." Chinese Journal of Chemistry 20, no. 11 (August 26, 2010): 1457–59. http://dx.doi.org/10.1002/cjoc.20020201152.

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26

Topa, Monika, Filip Petko, Mariusz Galek, Kamil Machowski, Maciej Pilch, Patryk Szymaszek, and Joanna Ortyl. "Applicability of 1,6-Diphenylquinolin-2-one Derivatives as Fluorescent Sensors for Monitoring the Progress of Photopolymerisation Processes and as Photosensitisers for Bimolecular Photoinitiating Systems." Polymers 11, no. 11 (October 25, 2019): 1756. http://dx.doi.org/10.3390/polym11111756.

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The applicability of new 1,6-diphenylquinolin-2-oneas derivatives as fluorescent molecular sensors for monitoring the progress of photopolymerisation processes by Fluorescence Probe Technique (FPT) has been tested. The progress of cationic, free-radical and thiol-ene photopolymerisation for commercially available monomers: triethylene glycol divinyl ether (TEGDVE), trimethylolpropane triacrylate (TMPTA) and trimethylpropane tris(3-mercaptopropropionate) (MERCAPTO) was monitored. It was found that new derivatives of 1,6-diphenylquinolin-2-one shifted their fluorescence spectra towards shorter wavelengths with the progress of polymerisation, which enabled monitoring the progress in terms of fluorescence intensity ratios as the progress indicator. Derivatives of 1,6-diphenylquinolin-2-one show sensitivity to changes in both polarity and viscosity in the surrounding microenvironment during photopolymerisation processes. Therefore, it was shown that they are good candidates to act as fluorescent sensors for monitoring the kinetics of very quick processes, such as photopolymerisation processes. Furthermore, the effect of the nature of substituents attached to the 1,6-diphenylquinolin-2-one ring on the characteristics of emission spectra was identified. Moreover, the sensitivity of fluorescent sensors was compared with commercially available model sensors, such as 7-diethylamino-4-methylcoumarin (Coumarin 1) and trans-2-(2′,5′-dimethoxyphenyl)ethenyl-2,3,4,5,6-pentafluorobenzene (25ST). Moreover, it was also proven that selected derivatives of 1,6-diphenylquinolin-2-one exhibit an accelerating effect on the progress of cationic photopolymerisation of vinyl monomers (TEGDVE). Thus, the new 1,6-diphenylquinolin-2-one derivatives can be successfully used both as molecular fluorescence sensors to monitor the progress of photopolymerisation processes and as diaryliodonium salt photosensitisers to initiate cationic photopolymerisation processes in a UV-A range of 365 nm.

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27

Pan, Jin-Long, Tao Chen, Zhi-Qiang Zhang, Yi-Fan Li, Xiao-Ming Zhang, and Fu-Min Zhang. "A Cu-mediated one-pot Michael addition/α-arylation strategy using a diaryliodonium salt: a direct and efficient approach to α-aryl-β-substituted cyclic ketone scaffolds." Chemical Communications 52, no. 11 (2016): 2382–85. http://dx.doi.org/10.1039/c5cc09837h.

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28

Wang, Hongzhen, Haohao Jiang, Shuizhen Lin, Shuoshuo Zhang, and Xiaolei Huang. "Diaryliodonium Salt‐Mediated Radical Transformation of Indoles with Alcohols for the Synthesis of Unsymmetrical Bis(indolyl)methanes." Advanced Synthesis & Catalysis, October 9, 2024. http://dx.doi.org/10.1002/adsc.202400827.

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A method for the synthesis of unsymmetrical bis(indolyl)methanes (BIMs) using simple indoles and readily available alcohols as the coupling partners under both heat and 390–400 nm light conditions was developed. Detailed research of the mechanism demonstrated that the diaryliodonium salt‐mediated transformation undergoes a nucleophilic hydroxymethyl radical formation process. Moreover, the diaryliodonium salt‐mediated method is also applicable for synthesizing symmetrical BIMs.

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29

Tomal, Wiktoria, Karolina Gałuszka, Petr Lepcio, Maciej Pilch, Anna Chachaj-Brekiesz, Martina Korčušková, and Joanna Ortyl. "Naphthalene-stilbenes as effective visible-light sensitizers to study the effect of diluent and nanofillers on in situ photopolymerization and 3D-VAT printing process." Materials Advances, 2023. http://dx.doi.org/10.1039/d3ma00943b.

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This study presents novel photoinitiating systems based on diaryliodonium salt (IOD) and 1-amino-4-methyl-6-styrylnaphthalene-2-carbonitrile derivatives developed as universal IOD photosensitizers. These systems' spectroscopic characteristics, electrochemical behavior, and thermodynamic parameters were investigated...

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30

Berntsen, Linn Neerbye, and Ainara Nova. "A Mechanistic Study of the Cu‐catalyzed N‐arylation of Hydantoin with Aryl(TMP)iodonium Salts." ChemCatChem, October 16, 2023. http://dx.doi.org/10.1002/cctc.202301057.

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The use of diaryliodonium salts in organic reactions has rapidly increased in the last decade because of their efficiency in arylation reactions. Despite this, mechanistic investigations are still scarce, particularly for copper catalyzed N‐arylation reactions. Recently, we published the use of the unsymmetrical aryl(TMP)iodonium salts (TMP = 2,4,6‐trimethoxyphenyl) for the selective Cu‐catalyzed N‐arylation of hydantoins. In this work, the mechanism of this reaction has been studied by DFT methods, and our results have been compared with previous and new experimental data. In contrast to the mechanism proposed for C‐H arylation reactions, our results suggest that deprotonation of hydantoin precedes the oxidative addition of aryl(TMP)iodonium salt, with the oxidative addition to a Cu(I) imido intermediate and ligand rearrangements being the rate‐limiting steps. This mechanism agrees with the species observed by NMR spectroscopy, kinetic isotope experiments, and the product yields observed using aryl(TMP)iodonium salts with different steric and electronic properties. In addition, it gives some hints for increasing the efficiency of arylation reactions by tuning the diaryliodonium salt.

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31

Wang, Haiwen, and Michael F. Greaney. "Regiodivergent Arylation of Pyridines via Zincke Intermediates." Angewandte Chemie, November 20, 2023. http://dx.doi.org/10.1002/ange.202315418.

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An arylation protocol for pyridines is described, via the ring‐opened Zincke intermediate. Treatment of pyridines with triflic anhydride and a secondary amine produces an azahexatriene species, which undergoes regioselective Pd‐catalyzed arylation at the putative C4 position. Recyclization then provides the pyridine products. Alternatively, metal‐free arylation with a diaryliodonium salt is selective for the pyridine meta‐position, affording a regiodivergent approach to pyridine biaryls from a common intermediate.

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32

Wang, Haiwen, and Michael F. Greaney. "Regiodivergent Arylation of Pyridines via Zincke Intermediates." Angewandte Chemie International Edition, November 20, 2023. http://dx.doi.org/10.1002/anie.202315418.

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An arylation protocol for pyridines is described, via the ring‐opened Zincke intermediate. Treatment of pyridines with triflic anhydride and a secondary amine produces an azahexatriene species, which undergoes regioselective Pd‐catalyzed arylation at the putative C4 position. Recyclization then provides the pyridine products. Alternatively, metal‐free arylation with a diaryliodonium salt is selective for the pyridine meta‐position, affording a regiodivergent approach to pyridine biaryls from a common intermediate.

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33

Crivello, James V. "Novel Photocurable Materials For Spinon Dielectric Films." MRS Proceedings 381 (1995). http://dx.doi.org/10.1557/proc-381-51.

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AbstractPoly(indanes) can be prepared by the photoinduced cationic polymerization of a variety of diisopropenyl aromatic monomers. Typically, polymerization proceeds rapidly under UV irradiation catalyzed by diaryliodonium salt photoinitiators to give hard, transparent films. Investigations have shown that the polymerization proceeds mainly by a dimerization followed by a ringclosure process to yield indane structures along the polymer backbone. Film-forming mixtures containing either pure monomer or mixtures of monomers together with a poly(indane) prepolymer can be spin coated onto silicon wafers. Measurements made on the photopolymerized coatings give low dielectric constants. These coatings also display excellent thermal stability.

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34

Chen, Xiang‐Long, Chun‐Yan Wu, Dong‐Sheng Yang, Bo‐Cheng Tang, Huai‐Yu Wang, Zhi‐Cheng Yu, Anling Li, Yan‐Dong Wu, and An‐Xin Wu. "Transition‐Metal‐Free Allylic Defluorination Cross‐Electrophile Coupling Employing Rongalite." Chinese Journal of Chemistry, February 23, 2024. http://dx.doi.org/10.1002/cjoc.202300751.

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Comprehensive SummaryThe conversion of CF3‐alkenes to gem‐difluoroalkenes using reductive cross‐coupling strategy has received much attention in recent years, however, the use of green and readily available reducing salt to mediate these reactions remains to be explored. In this work, a concise construction of gem‐difluoroalkenes, which requires neither a catalyst nor a metal reducing agent, was established. Rongalite, a safe and inexpensive industrial product, was employed as both a radical initiator and reductant. This procedure was compatible with both linear and cyclic diaryliodonium salts, enabling a wide variety of substrates (>70 examples). The utility of this approach was demonstrated through gram‐scale synthesis and efficient late‐stage functionalizations of anti‐inflammatory drugs.

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35

Manna, Kartic, and Ranjan Jana. "Palladium-Catalyzed Cross-Electrophile Coupling between Aryl Diazonium Salt and Aryl Iodide/Diaryliodonium Salt in H₂O–EtOH." Organic Letters, January 6, 2023. http://dx.doi.org/10.1021/acs.orglett.2c03932.

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36

Xu, Chunfa, Jiaxin Luo, Xinyu Chen, Wenyan Ding, Jialu Ma, Zhaohui Ni, and Lihuang Xie. "Transition-metal-free glycosyl sulfonation of diaryliodonium salt with sodium glycosyl sulfinate: an efficient approach to access glycosyl aryl sulfones." New Journal of Chemistry, 2024. http://dx.doi.org/10.1039/d3nj05942a.

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Glycosyl aryl sulfones have gained significant attention due to their diverse range of biological activities. However, the straightforward synthesis under mild conditions remains a challenging endeavor. This work presents the...

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37

Pan, Jin-Long, Tao Chen, Zhi-Qiang Zhang, Yi-Fan Li, Xiao-Ming Zhang, and Fu-Min Zhang. "ChemInform Abstract: A Cu-Mediated One-Pot Michael Addition/α-Arylation Strategy Using a Diaryliodonium Salt: A Direct and Efficient Approach to α-Aryl-β-Substituted Cyclic Ketone Scaffolds." ChemInform 47, no. 23 (May 2016). http://dx.doi.org/10.1002/chin.201623072.

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