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Journal articles on the topic 'Arene functionalization'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Gagnon, Jonathan, Martin Vézina, Marc Drouin, and Pierre D. Harvey. "Regioselective upper-rim functionalizations of calix[4]arene by diphenylphosphino groups." Canadian Journal of Chemistry 79, no. 10 (2001): 1439–46. http://dx.doi.org/10.1139/v01-161.

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The regioselective upper-rim functionalization of calix[4]arene have been performed to prepare all the multisubstituted diphenylphosphine derivatives. In addition, the X-ray structures of 5,17-dibromo-11,23-bis(diphenylphosphino)-25,26,27,28-tetra-n-propoxycalix[4]arene and 5,11,17,23-tetrakis(diphenylphosphino)-25,26,27,28-tetra-i-propoxy-calix[4]arene have been determined. Regioselective functionalizations have been achieved using methods that involve appropriate choices of bases, alkyllithium-solvent systems, stoichiometry, and reaction times. A new and convenient method for selectively pre

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2

Barluenga, J., E. Campos-Gómez, A. Minatti, D. Rodríguez, and J. González. "Iodonium Ion Triggered Arene Functionalization." Synfacts 2009, no. 12 (2009): 1342. http://dx.doi.org/10.1055/s-0029-1218180.

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3

Wang, Xia, Ya-Fei Han, Xuan-Hui Ouyang, Ren-Jie Song, and Jin-Heng Li. "The photoredox alkylarylation of styrenes with alkyl N-hydroxyphthalimide esters and arenes involving C–H functionalization." Chemical Communications 55, no. 97 (2019): 14637–40. http://dx.doi.org/10.1039/c9cc07494e.

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The In(OTf)<sub>3</sub>-promoted three-component photoredox alkylarylation of styrenes with alkyl NHP esters and arenes to access alkylated arene derivatives through C–C bond cleavage and C–H functionalization is reported.

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4

Nierengarten, Iwona, Michel Holler, Marine Rémy, et al. "Grafting Dendrons onto Pillar[5]Arene Scaffolds." Molecules 26, no. 8 (2021): 2358. http://dx.doi.org/10.3390/molecules26082358.

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With their ten peripheral substituents, pillar[5]arenes are attractive compact scaffolds for the construction of nanomaterials with a controlled number of functional groups distributed around the macrocyclic core. This review paper is focused on the functionalization of pillar[5]arene derivatives with small dendrons to generate dendrimer-like nanomaterials and bioactive compounds. Examples include non-viral gene vectors, bioactive glycoclusters, and liquid-crystalline materials.

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5

Tarnovskiy, Andriy, Alexander Shivanyuk, and Vladimir V. Rozhkov. "Selective functionalization of a resorcin[6]arene." Tetrahedron 67, no. 50 (2011): 9715–18. http://dx.doi.org/10.1016/j.tet.2011.10.043.

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6

Wang, Guo, Hui Qiang, Yun-Zhe Guo, Jie Yang, Ke Wen, and Wei-Bo Hu. "Systematic rim cyano-functionalization of pillar[5]arene and corresponding host–guest property varieties." Organic & Biomolecular Chemistry 17, no. 18 (2019): 4600–4604. http://dx.doi.org/10.1039/c9ob00396g.

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Synthetic investigation of the systematic replacement of alkoxy groups in pillar[5]arene by cyano ones was carried out. Host–guest property studies of nCN-pillar[5]arenes and 1,4-dicyanobutane showed the functionization number related host–guest interaction varieties.

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7

Olteanu, Marius, Raluca Septelean, Ovidiu Nemes, et al. "Functionalization of Mesoporous Silica Materials Using Calix[4]arenes." Materiale Plastice 56, no. 3 (2019): 554–58. http://dx.doi.org/10.37358/mp.19.3.5228.

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\Six new products were obtained by deposition of para-tert-butylcalix[4]arene (t-Bu-C4OH), calix[4]arene (C4OH) and tetra-methoxy-calix[4]arene (C4OMe) on two types of SBA-15 mesoporous silica. All the products were characterized through thermogravimetric methods and SEM microscopy. The obtained results confirm the functionalization of the silica materials with the calixarene macrocycles. Considering all the obtained products, the thermal analysis suggests the strongest connectivity to form between the C4OMe systems and mesoporous silica substrate.

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8

NAM, K. C., and K. S. PARK. "ChemInform Abstract: Selective Functionalization of Calix(6)arene." ChemInform 26, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199545121.

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9

Dutta, Uttam, Sudip Maiti, Trisha Bhattacharya, and Debabrata Maiti. "Arene diversification through distal C(sp2)−H functionalization." Science 372, no. 6543 (2021): eabd5992. http://dx.doi.org/10.1126/science.abd5992.

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Transition metal–catalyzed aryl C−H activation is a powerful synthetic tool as it offers step and atom-economical routes to site-selective functionalization. Compared with proximal ortho-C−H activation, distal (meta- and/or para-) C−H activation remains more challenging due to the inaccessibility of these sites in the formation of energetically favorable organometallic pretransition states. Directing the catalyst toward the distal C−H bonds requires judicious template engineering and catalyst design, as well as prudent choice of ligands. This review aims to summarize the recent elegant discove

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10

Al-Azemi, Talal F., Mickey Vinodh, Fatemeh H. Alipour, and Abdirahman A. Mohamod. "Synthesis, functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent." RSC Advances 9, no. 40 (2019): 23295–301. http://dx.doi.org/10.1039/c9ra03135a.

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Bulky perneopentyloxy-pillar[5]arene was synthesized. Complexation behavior and conformational mobility were investigated using <sup>1</sup>H NMR spectroscopy. Isolation of planar-chiral pillar[5]arenes using a chiral derivatization agent were carried out.

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11

Firdaus, Firdaus, Jumina Jumina, and Hardjono Sastrohamidjojo. "EFFECT OF DE-tert-BUTYLATION AND FUNCTIONALIZATION WITH AMINE GROUPS AT THE UPPER RIM OF p-tert-BUTYLCALIX[4]ARENE TO THE EXTRACTABILITY FOR Cr³⁺, Cd²⁺ and Pb²⁺ IONS." Indonesian Journal of Chemistry 7, no. 3 (2010): 289–96. http://dx.doi.org/10.22146/ijc.21671.

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The effects to the extractability forwards Cr3+, Cd2+, and Pb2+ ions of de-tert-butylation and functionalization with amine groups at the upper rim of p-tert-butylcalix[4]arene had been studied by applied the p-tert-butylcalix[4]arene (1), tetrahydroxycalix[4]arene (2), and p-(amino)butoxycalixarene (3) compounds as extractants for the heavy metals ions. The extraction involved optimise of three parameters, i.e. pH, time, and concentration of extractants. The extraction degrees of the heavy metals ions at optimum conditions were compared each other to decide the effects. Compound 1 showed high

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12

Riedl, Christoph A., Michaela Hejl, Matthias H. M. Klose, et al. "N- and S-donor leaving groups in triazole-based ruthena(ii)cycles: potent anticancer activity, selective activation, and mode of action studies." Dalton Transactions 47, no. 13 (2018): 4625–38. http://dx.doi.org/10.1039/c8dt00449h.

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13

Schomaker, Jennifer, and R. Grigg. "Activating Group Recycling: A Fresh Approach to Arene Functionalization." Synlett 24, no. 04 (2012): 401–7. http://dx.doi.org/10.1055/s-0032-1317953.

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14

NAM, K. C., and T. H. YOON. "ChemInform Abstract: Functionalization of p-1,3-Diallylcalix(4)arene." ChemInform 24, no. 46 (2010): no. http://dx.doi.org/10.1002/chin.199346142.

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15

van Wageningen, Andr� M. A., John P. M. van Duynhoven, Willem Verboom, and David N. Reinhoudt. "Synthesis and functionalization of calix[4]arene-based carceplexes." Journal of the Chemical Society, Chemical Communications, no. 19 (1995): 1941. http://dx.doi.org/10.1039/c39950001941.

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16

Kumar, Sanjeev, Saiprasad Nunewar, Srilekha Oluguttula, Srinivas Nanduri, and Vinaykumar Kanchupalli. "Recent advances in Rh(iii)/Ir(iii)-catalyzed C–H functionalization/annulation via carbene migratory insertion." Organic & Biomolecular Chemistry 19, no. 7 (2021): 1438–58. http://dx.doi.org/10.1039/d0ob02309d.

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The review highlighted diverse annulations, including nitrogen, oxygen, sulfur heterocycles and carbocylizations via Rh(iii)/Ir(iii)-catalyzed C–H functionalization/annulation with various arene and carbene precursors.

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17

Klenke, Burkhard, Christian Näther, and Willy Friedrichsen. "Selective side-chain functionalization of a calix[4]arene-2,8,14,20-tetrabromo-25,26,27,28-tetramethoxycalix[4]arene -." Tetrahedron Letters 39, no. 49 (1998): 8967–68. http://dx.doi.org/10.1016/s0040-4039(98)02056-5.

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18

Lee, Da Seul, Chung Soo Kim, Naila Iqbal, Gyeong Su Park, Kyung-sun Son, and Eun Jin Cho. "Organophotocatalytic Arene Functionalization: C–C and C–B Bond Formation." Organic Letters 21, no. 24 (2019): 9950–53. http://dx.doi.org/10.1021/acs.orglett.9b03877.

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19

Casnati, Alessandro, Riccardo Ferdani, Andrea Pochini, and Rocco Ungaro. "p-(Benzyloxy)calix[8]arene: One-Pot Synthesis and Functionalization." Journal of Organic Chemistry 62, no. 18 (1997): 6236–39. http://dx.doi.org/10.1021/jo970620r.

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20

Ben Hadj Amor, Abir, Siden Top, Faouzi Meganem, and Gérard Jaouen. "Selective functionalization of crown ethers via arene chromium tricarbonyl complexes." Journal of Organometallic Chemistry 690, no. 4 (2005): 847–56. http://dx.doi.org/10.1016/j.jorganchem.2004.09.090.

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21

Zhou, Yang, Jing Zhao, and Lei Liu. "Meta-Selective Transition-Metal Catalyzed Arene CH Bond Functionalization." Angewandte Chemie International Edition 48, no. 39 (2009): 7126–28. http://dx.doi.org/10.1002/anie.200902762.

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22

Krüger, Tobias, Katja Vorndran, and Torsten Linker. "Regioselective Arene Functionalization: Simple Substitution of Carboxylate by Alkyl Groups." Chemistry - A European Journal 15, no. 44 (2009): 12082–91. http://dx.doi.org/10.1002/chem.200901774.

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23

Zeng, Rong, Juntao Ye, Chunling Fu, and Shengming Ma. "Arene CH Bond Functionalization Coupling with Cyclization of Allenes." Advanced Synthesis & Catalysis 355, no. 10 (2013): 1963–70. http://dx.doi.org/10.1002/adsc.201300408.

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24

Ding, Wei-Yi, Peiyuan Yu, Qian-Jin An, et al. "DFT-Guided Phosphoric-Acid-Catalyzed Atroposelective Arene Functionalization of Nitrosonaphthalene." Chem 6, no. 8 (2020): 2046–59. http://dx.doi.org/10.1016/j.chempr.2020.06.001.

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25

Decken, Andreas, Pierre D. Harvey, and Jasmin Douville. "5,17-Diformyl-25,26,27,28-tetrabenzyloxycalix[4]arene: functionalization of the upper rim of a calix[4]arene." Acta Crystallographica Section E Structure Reports Online 60, no. 7 (2004): o1170—o1171. http://dx.doi.org/10.1107/s1600536804013595.

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26

Okumura, Mikiko, and David Sarlah. "Arenophile-Mediated Photochemical Dearomatization of Nonactivated Arenes." CHIMIA International Journal for Chemistry 74, no. 7 (2020): 577–83. http://dx.doi.org/10.2533/chimia.2020.577.

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Aromatic compounds are one of the most abundant classes of organic molecules and find utility as precursors for alicyclic hydrocarbon building blocks. While many established dearomatization reactions are exceptionally powerful, dearomatization with concurrent introduction of functionality, i.e. dearomative functionalization, is still a largely underdeveloped field. This review aims to provide an overview of our recent efforts and progress in the development of dearomative functionalization of simple and nonactivated arenes using arenophile-arene cycloaddition platform. These cycloadducts, form

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27

Kirila, Tatyana, Alina Amirova, Alexey Blokhin, Andrey Tenkovtsev, and Alexander Filippov. "Features of Solution Behavior of Polymer Stars with Arms of Poly-2-alkyl-2-oxazolines Copolymers Grafted to the Upper Rim of Calix[8]arene." Polymers 13, no. 15 (2021): 2507. http://dx.doi.org/10.3390/polym13152507.

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Star-shaped polymers with arms of block and gradient copolymers of 2-ethyl- and 2-isopropyl-2-oxazolines grafted to the upper rim of calix[8]arene were synthesized by the “grafting from” method. The ratio of 2-ethyl- and 2-isopropyl-2-oxazoline units was 1:1. Molar masses and hydrodynamic characteristics were measured using molecular hydrodynamics and optics methods in 2-nitropropane. The arms of the synthesized stars were short and the star-shaped macromolecules were characterized by compact dimensions and heightened intramolecular density. The influence of the arm structure on the conformati

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28

Prim, Damien, and Benjamin Large. "C–H Functionalization Strategies in the Naphthalene Series: Site Selections and Functional Diversity." Synthesis 52, no. 18 (2020): 2600–2612. http://dx.doi.org/10.1055/s-0040-1707855.

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Naphthalene is certainly not a common arene. In contrast to benzene, the bicyclic feature of naphthalene offers multiple differentiable positions and thus a broad diversity of substitution patterns. Naphthalene is a central building block for the construction of elaborated polycyclic architectures with applications in broad domains such as life and materials sciences. As a result, C–H functionalization strategies specially designed for naphthalene substrates have become essential to install valuable substituents on one or both rings towards polysubstituted naphthalenes. This short review provi

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29

Dutta, Uttam, Atanu Modak, Bangaru Bhaskararao, et al. "Catalytic Arene meta-C–H Functionalization Exploiting a Quinoline-Based Template." ACS Catalysis 7, no. 5 (2017): 3162–68. http://dx.doi.org/10.1021/acscatal.7b00247.

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30

Postils, Verònica, Mònica Rodríguez, Gerard Sabenya, et al. "Mechanism of the Selective Fe-Catalyzed Arene Carbon–Hydrogen Bond Functionalization." ACS Catalysis 8, no. 5 (2018): 4313–22. http://dx.doi.org/10.1021/acscatal.7b03935.

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31

Berthalon, Sandrine, Jean-Bernard Regnouf-de-Vains, and Roger Lamartine. "Mono-functionalization of the tris-(p-tert-butyl)calix[4]arene." Tetrahedron Letters 38, no. 49 (1997): 8527–28. http://dx.doi.org/10.1016/s0040-4039(97)10305-7.

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32

Quideau, Stéphane, and Ken S. Feldman. "Oxidative activation of aromatic rings: an efficient strategy for arene functionalization." Tetrahedron 57, no. 2 (2001): ix—x. http://dx.doi.org/10.1016/s0040-4020(00)00933-9.

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33

Zhou, Yang, Jing Zhao, and Lei Liu. "ChemInform Abstract: Metaselective Transition Metal Catalyzed Arene CâH Bond Functionalization." ChemInform 40, no. 51 (2009): no. http://dx.doi.org/10.1002/chin.200951227.

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34

Biancalana, Lorenzo, Martyna Gruchała, Lucinda K. Batchelor, et al. "Conjugating Biotin to Ruthenium(II) Arene Units via Phosphine Ligand Functionalization." European Journal of Inorganic Chemistry 2020, no. 11-12 (2019): 1061–72. http://dx.doi.org/10.1002/ejic.201900922.

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35

Schomaker, Jennifer M., and R. David Grigg. "ChemInform Abstract: Activating Group Recycling: A Fresh Approach to Arene Functionalization." ChemInform 44, no. 19 (2013): no. http://dx.doi.org/10.1002/chin.201319261.

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36

Ghosh, Koushik, Raja K. Rit, Majji Shankar, Kallol Mukherjee, and Akhila K. Sahoo. "Directing Group Assisted Unsymmetrical Multiple Functionalization of Arene C−H Bonds." Chemical Record 20, no. 9 (2020): 1017–42. http://dx.doi.org/10.1002/tcr.202000063.

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37

VAN WAGENINGEN, A. M. A., J. P. M. VAN DUYNHOVEN, W. VERBOOM, and D. N. REINHOUDT. "ChemInform Abstract: Synthesis and Functionalization of Calix(4)arene-Based Carceplexes." ChemInform 27, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.199608179.

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38

Schmidt, Bernd, and Nelli Elizarov. "Selective arene functionalization through sequential oxidative and non-oxidative Heck reactions." Chemical Communications 48, no. 36 (2012): 4350. http://dx.doi.org/10.1039/c2cc30752a.

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39

Kogan, Katerina, Ishay Columbus, and Silvio E. Biali. "Functionalization of the Methylene Bridges of the Calix[6]arene Scaffold." Journal of Organic Chemistry 73, no. 18 (2008): 7327–35. http://dx.doi.org/10.1021/jo801187z.

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40

Pan, Shuai, De-Xian Wang, Liang Zhao, and Mei-Xiang Wang. "Synthesis and Functionalization of Inherently Chiral Tetraoxacalix[2]arene[2]pyridines." Organic Letters 14, no. 24 (2012): 6254–57. http://dx.doi.org/10.1021/ol303019q.

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41

Zhang, Bo-Sheng, Hui-Liang Hua, Lu-Yao Gao, et al. "Palladium-catalyzed arene C–H activation/ketone C–H functionalization reaction: route to spirodihydroindenones." Organic Chemistry Frontiers 4, no. 7 (2017): 1376–79. http://dx.doi.org/10.1039/c7qo00164a.

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42

Mongrain, Pascal, Jasmin Douville, Jonathan Gagnon, et al. "New insights about the hostguest chemistry of the tungsten oxo complex of calix[4]arene, and novel "one pot" difunctionalizations of calix[4]arene using tetrachlorometal(VI) oxide (M = Mo, W)." Canadian Journal of Chemistry 82, no. 10 (2004): 1452–61. http://dx.doi.org/10.1139/v04-097.

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The strong Lewis acid tungsten oxo complex of calix[4]arene can be obtained in both hydrated and non-hydrated forms. This complex coordinates a water molecule inside the cavity via strong O···W interactions with relatively short distances of 2.284(4) and 2.329(2) Å for the tungsten oxo complex of calix[4]arene··H2O·aniline (1), and the tungsten oxo complex of calix[4]arene·H2O·toluene (2·toluene), respectively. The strong interactions are also deduced by the relatively high H2O elimination temperature observed by TGA and DSC (above 200 °C). The coordinated water molecule inside the calix[4]are

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43

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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44

Zhang, Chen, Rahul S. Patil, Charles L. Barnes, and Jerry L. Atwood. "Preparation of Anionic Metal-Seamed Pyrogallol[4]arene Nanocapsules via Surface Functionalization." Crystal Growth & Design 17, no. 9 (2017): 4541–43. http://dx.doi.org/10.1021/acs.cgd.7b00968.

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45

Agbaria, Kasim, and Silvio E. Biali. "Spirodienone Route for the Stereoselective Methylene Functionalization ofp-tert-Butylcalix[4]arene." Journal of the American Chemical Society 123, no. 50 (2001): 12495–503. http://dx.doi.org/10.1021/ja0117480.

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46

Itzhak, Norbert, and Silvio E. Biali. "Selective Functionalization of a Single Methylene Bridge of a Calix[6]arene." Journal of Organic Chemistry 75, no. 10 (2010): 3437–42. http://dx.doi.org/10.1021/jo1005476.

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47

CASNATI, A., R. FERDANI, A. POCHINI, and R. UNGARO. "ChemInform Abstract: p-(Benzyloxy)calix[8]arene: One-Pot Synthesis and Functionalization." ChemInform 29, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199803103.

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48

Zeng, Rong, Juntao Ye, Chunling Fu, and Shengming Ma. "ChemInform Abstract: Arene C-H Bond Functionalization Coupling with Cyclization of Allenes." ChemInform 44, no. 50 (2013): no. http://dx.doi.org/10.1002/chin.201350109.

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49

Savithri, Anupriya, Sreeja Thulasi, and Ramavarma Luxmi Varma. "Narrow-Rim Functionalization of Calix[4]arene through Ugi-4CR: Synthesis of a Series of Calix[4]arene Peptoids." Journal of Organic Chemistry 79, no. 4 (2014): 1683–89. http://dx.doi.org/10.1021/jo4025732.

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50

Ortega, Enrique, Jyoti G. Yellol, Matthias Rothemund, et al. "A new C,N-cyclometalated osmium(ii) arene anticancer scaffold with a handle for functionalization and antioxidative properties." Chemical Communications 54, no. 79 (2018): 11120–23. http://dx.doi.org/10.1039/c8cc06427j.

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