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Journal articles on the topic 'Ullmann ether synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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1

Keipour, Hoda, Abolfazl Hosseini, Amir Afsari, Razieh Oladee, Mohammad A. Khalilzadeh, and Thierry Ollevier. "CsF/clinoptilolite: an efficient solid base in SNAr and copper-catalyzed Ullmann reactions." Canadian Journal of Chemistry 94, no. 1 (2016): 95–104. http://dx.doi.org/10.1139/cjc-2015-0300.

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CsF/clinoptilolite was found to be an efficient solid base catalyst for both SNAr and Ullmann ether reactions. A general and efficient one-step procedure was developed for the synthesis of biaryl ethers via direct coupling of electron-deficient aryl halides to phenols using CsF/clinoptilolite. The protocol was also applied to electron-rich aryl halides by addition of a catalytic amount of copper oxide nanoparticles. Both SNAr and Ullmann reactions were rapid and provided good to excellent yields.

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2

Ren, Rex X., Yunting Luo, and Jeff Xin Wu. "Ullmann Diaryl Ether Synthesis in Ionic Liquids." Synlett, no. 11 (2003): 1734–36. http://dx.doi.org/10.1055/s-2003-41432.

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3

Abe, Hitoshi, Haruka Imai, Yuta Kanzaka, and Yukinari Sunatsuki. "Synthesis of Nilotinin M3: An Ellagitannin Containing an Isodehydrodigalloyl Group." Synthesis 53, no. 19 (2021): 3630–38. http://dx.doi.org/10.1055/a-1508-9541.

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AbstractTotal synthesis of nilotinin M3, which is a member of the ellagitannin family of natural products containing an isodehydrodigalloyl (isoDHDG) group, was achieved using the Ullmann reaction to construct a highly functionalized diaryl ether.

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4

Fossum, Eric, Zhenning Yu, and Loon-Seng Tan. "Aryl ether synthesis via low-cost Ullmann coupling systems." Arkivoc 2009, no. 14 (2010): 255–65. http://dx.doi.org/10.3998/ark.5550190.0010.e23.

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5

OI, Ryu, Chitoshi Shimakawa, and Shinji Takenaka. "Ullmann Ether Synthesis in DMI. Preparation ofm-Phenoxybenzyl Alcohol." Chemistry Letters 17, no. 5 (1988): 899–900. http://dx.doi.org/10.1246/cl.1988.899.

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6

Park, Sooyoung, Seok-Ho Kim, Jin-Hyun Jeong, and Dongyun Shin. "Total synthesis of giffonin H by fluoride-catalyzed macrocyclization." Organic Chemistry Frontiers 6, no. 5 (2019): 704–8. http://dx.doi.org/10.1039/c8qo01303a.

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First total synthesis of giffonin H, a highly strained 15-membered macrocyclic diaryl ether, has been achieved. Key steps include Ullmann cross coupling, (Z)-selective Julia–Kocienski olefination, and fluoride-mediated macrocyclization of TMS-alkyne and aldehyde. The strategy used for macrocyclization is an unprecedented and unique synthetic approach for cyclic diarylheptanoids.

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7

Palomo, Claudio, Mikel Oiarbide, Rosa López, and Enrique Gómez-Bengoa. "Phosphazene P4-But base for the Ullmann biaryl ether synthesis." Chemical Communications, no. 19 (1998): 2091–92. http://dx.doi.org/10.1039/a805783d.

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8

Ragan, Mark A. "Brown algal polyphenols: synthesis of "fucophlorethol A" octamethyl ether (2,2′,4,6,6′-pentamethoxy-4′-(2,4,6-trimethoxyphenoxy)biphenyl)." Canadian Journal of Chemistry 63, no. 2 (1985): 291–93. http://dx.doi.org/10.1139/v85-049.

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Vanadium tetrachloride-catalyzed dimerization of 3,5-dimethoxyphenol yields the key intermediate 2,2′,6,6′-tetra-methoxy-4,4′-dihydroxybiphenyl, from which the octamethyl ether of the brown algal metabolite "fucophlorethol A" (2,2′,4,6,6′-pentamethoxy-4′-(2,4,6-trimethoxyphenoxy)biphenyl, 6) is synthesized by Ullmann condensation and Hakomori methylation.

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9

Otto, Nicola, and Till Opatz. "Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers." Beilstein Journal of Organic Chemistry 8 (July 17, 2012): 1105–11. http://dx.doi.org/10.3762/bjoc.8.122.

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In the search for new ligands for the Ullmann diaryl ether synthesis, permitting the coupling of electron-rich aryl bromides at relatively low temperatures, 56 structurally diverse multidentate ligands were screened in a model system that uses copper iodide in acetonitrile with potassium phosphate as the base. The ligands differed largely in their performance, but no privileged structural class could be identified.

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10

Wu, Jian, Xu-Liang Jiang, and Hong-Liang Zhang. "Synthesis of Diaryl Ether-Linked Porphyrin Dimers via Ullmann Coupling Reaction." HETEROCYCLES 68, no. 10 (2006): 2153. http://dx.doi.org/10.3987/com-06-10816.

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11

Buck, Elizabeth, Zhiguo Jake Song, David Tschaen, Peter G. Dormer, R. P. Volante, and Paul J. Reider. "Ullmann Diaryl Ether Synthesis: Rate Acceleration by 2,2,6,6-Tetramethylheptane-3,5-dione." Organic Letters 4, no. 9 (2002): 1623–26. http://dx.doi.org/10.1021/ol025839t.

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12

Zhang, Baohua, Lanxiang Shi, Ruixia Guo, and Sijie Liu. "Ullmann diaryl ether synthesis catalyzed by copper (I)/pyridine-functionalized silane." Phosphorus, Sulfur, and Silicon and the Related Elements 191, no. 6 (2016): 930–32. http://dx.doi.org/10.1080/10426507.2015.1119135.

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13

Lee, Jong Il, Lee Young Kwon, Ji-Heung Kim, Kil-Yeong Choi, and Dong Hack Suh. "Synthesis of new poly(aryl ether)s with pendent benzoxazole groups via Ullmann ether reaction." Die Angewandte Makromolekulare Chemie 254, no. 1 (1998): 27–32. http://dx.doi.org/10.1002/(sici)1522-9505(19980201)254:1<27::aid-apmc27>3.0.co;2-9.

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14

Engels, Volker, Faysal Benaskar, Narendra Patil, et al. "Cu-Based Nanoalloys in the Base-Free Ullmann Heterocyle-Aryl Ether Synthesis." Organic Process Research & Development 14, no. 3 (2010): 644–49. http://dx.doi.org/10.1021/op9003423.

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15

PALOMO, C., M. OIARBIDE, R. LOPEZ, and E. GOMEZ-BENGOA. "ChemInform Abstract: Phosphazene P4-But Base for the Ullmann Biaryl Ether Synthesis." ChemInform 30, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199901094.

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16

Fui, Choong Jian, Mohd Sani Sarjadi, Shaheen M. Sarkar, and Md Lutfor Rahman. "Recent Advancement of Ullmann Condensation Coupling Reaction in the Formation of Aryl-Oxygen (C-O) Bonding by Copper-Mediated Catalyst." Catalysts 10, no. 10 (2020): 1103. http://dx.doi.org/10.3390/catal10101103.

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Transition metal-catalyzed chemical transformation of organic electrophiles and organometallic reagents belong to the most important cross coupling reaction in organic synthesis. The biaryl ether division is not only popular in natural products and synthetic pharmaceuticals but also widely found in many pesticides, polymers, and ligands. Copper catalyst has received great attention owing to the low toxicity and low cost. However, traditional Ullmann-type couplings suffer from limited substrate scopes and harsh reaction conditions. The introduction of homogeneous copper catalyst with presence o

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17

Klein, Daniel J., Bum-Sung Kim, and Frank W. Harris. "Synthesis of poly(aryl ether phenylquinoxaline) via Ullmann ether condensation of chlorine-substituted A-B quinoxaline monomers." Polymer Bulletin 47, no. 3-4 (2001): 217–21. http://dx.doi.org/10.1007/s289-001-8174-x.

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18

Liu, Bei, Zheng Chen, Liming Lin, Yuntao Han, Jinhui Pang, and Zhenhua Jiang. "Synthesis and characterization of poly(arylene ether ketone)s with 3,6-diphenyl-9H-carbazole pendants using C–N coupling reaction." High Performance Polymers 29, no. 5 (2016): 575–84. http://dx.doi.org/10.1177/0954008316655592.

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3,6-Diphenyl-9 H-carbazole pendants are grafted herein to poly(arylene ether ketone)s (PAEKs) via the Ullmann C–N coupling reaction. To the best of our knowledge, this is the first time that PAEKs containing a carbazole pendant (Cz) have been synthesized through the Ullmann C–N coupling reaction. The high molecular weights of PAEK-Cz (PAEKs with 3,6-diphenyl-9 H-carbazole pendants) are inherited from their precursors, owing to the high reactivity of their monomers. The obtained PAEK-Cz- x polymers exhibit good solubility in most common organic solvents and excellent thermal stabilities, with t

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19

Buck, Elizabeth, Zhiguo Jake Song, David Tschaen, Peter G. Dormer, R. P. Volante, and Paul J. Reider. "ChemInform Abstract: Ullmann Diaryl Ether Synthesis: Rate Acceleration by 2,2,6,6-Tetramethylheptane-3,5-dione." ChemInform 33, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.200238076.

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20

Benaskar, F., N. G. Patil, V. Engels, et al. "Microwave-assisted Cu-catalyzed Ullmann ether synthesis in a continuous-flow milli-plant." Chemical Engineering Journal 207-208 (October 2012): 426–39. http://dx.doi.org/10.1016/j.cej.2012.06.147.

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21

D’Angelo, Noel D., Joseph J. Peterson, Shon K. Booker, et al. "Effect of microwave heating on Ullmann-type heterocycle-aryl ether synthesis using chloro-heterocycles." Tetrahedron Letters 47, no. 29 (2006): 5045–48. http://dx.doi.org/10.1016/j.tetlet.2006.05.103.

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22

Khalilzadeh, Mohammad A., Hoda Keipour, Abolfazl Hosseini, and Daryoush Zareyee. "KF/Clinoptilolite, an effective solid base in Ullmann ether synthesis catalyzed by CuO nanoparticles." New J. Chem. 38, no. 1 (2014): 42–45. http://dx.doi.org/10.1039/c3nj00834g.

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23

Al-Zoubi, Raed M., Reem M. Altamimi, Walid K. Al-Jammal, et al. "CuI-Catalyzed Ullmann-Type Coupling of Phenols and Thiophenols with 5-Substituted 1,2,3-Triiodobenzenes: Facile Synthesis of Mammary Carcinoma Inhibitor BTO-956 in One Step." Synthesis 53, no. 15 (2021): 2665–75. http://dx.doi.org/10.1055/a-1458-2980.

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AbstractA facile and unprecedented synthesis of 2,3-diiodinated or 2,6-diiodinated diaryl ether/thioether derivatives through regioselective Ullmann-type cross couplings of 5-substituted 1,2,3-triiodobenzenes and phenols/thiophenols is described. Remarkably, the coupling reactions are simply controlled by the type of nucleophiles and the nature of C5 substituent at 1,2,3-triiodoarenes providing the internal or terminal coupling products in high regioselectivity and good isolated yields. Noticeable steric and electronic effects were clearly observed on both 1,2,3-triiodoarenes and nucleophiles.

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24

Rao, A. V. Rama, T. K. Chakraborty, K. Laxma Reddy, and A. Srinivasa Rao. "-nitro-promoted Ullmann ether synthesis : Application in the syntheses of K-13 and the isodityrosine unit of vancomycin." Tetrahedron Letters 33, no. 33 (1992): 4799–802. http://dx.doi.org/10.1016/s0040-4039(00)61289-3.

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25

Benaskar, Faysal, Volker Engels, Narendra Patil, et al. "Copper(0) in the Ullmann heterocycle-aryl ether synthesis of 4-phenoxypyridine using multimode microwave heating." Tetrahedron Letters 51, no. 2 (2010): 248–51. http://dx.doi.org/10.1016/j.tetlet.2009.10.126.

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26

Khalilzadeh, Mohammad A., Hoda Keipour, Abolfazl Hosseini, and Daryoush Zareyee. "ChemInform Abstract: KF/Clinoptilolite, An Effective Solid Base in Ullmann Ether Synthesis Catalyzed by CuO Nanoparticles." ChemInform 45, no. 22 (2014): no. http://dx.doi.org/10.1002/chin.201422102.

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27

Magné, Valentin, Tony Garnier, Mathieu Danel, Patrick Pale, and Stefan Chassaing. "CuI–USY as a Ligand-Free and Recyclable Catalytic System for the Ullmann-Type Diaryl Ether Synthesis." Organic Letters 17, no. 18 (2015): 4494–97. http://dx.doi.org/10.1021/acs.orglett.5b02167.

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28

Zhou, Qizhong, Liangjun Su, Tiansheng Jiang, et al. "Copper/iron-catalyzed Ullmann coupling of diiodo- and dibromoarenes and diphenols for the synthesis of aryl ether macrocycles." Tetrahedron 70, no. 6 (2014): 1125–32. http://dx.doi.org/10.1016/j.tet.2013.12.089.

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29

Wang, Jinyan, Yan Gao, Antisar R. Hlil, and Allan S. Hay. "Synthesis of High Molecular Weight Poly(phthalazinone ether)s by Ullmann C−N and C−O Condensation Reactions." Macromolecules 41, no. 2 (2008): 298–300. http://dx.doi.org/10.1021/ma702039a.

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30

Hussain, Zahid, Cristiane Schwalm, Raoní Rambo, Renieidy Dias, Rafael Stieler, and Adriano Monteiro. "Synthesis of Mono- and Bis-Pyrazoles Bearing Flexible p-Tolyl Ether and Rigid Xanthene Backbones, and Their Potential as Ligands in the Pd-Catalysed Suzuki–Miyaura Cross-Coupling Reaction." Catalysts 9, no. 9 (2019): 718. http://dx.doi.org/10.3390/catal9090718.

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The present work describes the synthesis of mono- and bis-pyrazole compounds bearing flexible p-tolyl ether and rigid 4,5-dibromo-2,7-di-tert-butyl-9,9-dimethyl-9H-xanthene backbones as pyrazolyl analogues of DPEphos and Xantphos ligands, respectively. The synthesis of new pyrazolyl analogues was accomplished following an Ullmann coupling protocol, and the resulting products were isolated in overall good yields. In addition, a hybrid imidazolyl–pyrazolyl analogue bearing a xanthene backbone was synthesized using the same protocol, whereas a hybrid selanyl–pyrazolyl analogue with a xanthene bac

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31

Al-tarawneh, Suha S., Taher Ababneh, and Ibtesam Aljaafreh. "Amination of ether-linked polymers via the application of Ullmann-coupling reaction: synthesis, characterization, porosity, and thermal stability evaluation." International Journal of Polymer Analysis and Characterization 26, no. 7 (2021): 618–29. http://dx.doi.org/10.1080/1023666x.2021.1947662.

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32

Zhou, Qizhong, and et al et al. "ChemInform Abstract: Copper/Iron-Catalyzed Ullmann Coupling of Diiodo- and Dibromoarenes and Diphenols for the Synthesis of Aryl Ether Macrocycles." ChemInform 45, no. 27 (2014): no. http://dx.doi.org/10.1002/chin.201427196.

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33

Benaskar, Faysal, Volker Engels, Narendra Patil, et al. "Corrigendum to “Copper(0) in the Ullmann heterocycle-aryl ether synthesis of 4-phenoxypyridine using multimode microwave heating” [Tetrahedron Lett. 51 (2010) 248]." Tetrahedron Letters 51, no. 44 (2010): 5849. http://dx.doi.org/10.1016/j.tetlet.2010.09.001.

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34

Giri, Ramesh, Andrew Brusoe, Konstantin Troshin, Justin Y. Wang, Marc Font, and John F. Hartwig. "Mechanism of the Ullmann Biaryl Ether Synthesis Catalyzed by Complexes of Anionic Ligands: Evidence for the Reaction of Iodoarenes with Ligated Anionic CuI Intermediates." Journal of the American Chemical Society 140, no. 2 (2018): 793–806. http://dx.doi.org/10.1021/jacs.7b11853.

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35

Tsubogo, Tetsu, Fumiya Okamura, Akiho Omori, and Hiromi Uchiro. "An Efficient and Short Total Synthesis of (−)‐Heliannuol A by Intramolecular Ullmann C−O Coupling for the Construction of an Eight‐Membered Ether Ring." ChemistrySelect 6, no. 17 (2021): 4224–28. http://dx.doi.org/10.1002/slct.202100355.

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36

Olivera, Roberto, Raul SanMartin, Fátima Churruca, and Esther Domínguez. "Revisiting the Ullmann−Ether Reaction: A Concise and Amenable Synthesis of Novel Dibenzoxepino[4,5-d]pyrazoles by Intramolecular Etheration of 4,5-(o,o‘-Halohydroxy)arylpyrazoles." Journal of Organic Chemistry 67, no. 21 (2002): 7215–25. http://dx.doi.org/10.1021/jo025767j.

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37

Rashmi, P., Gopal Krishna Rao, Kshama Devi, B. G. Shivananda, G. R. Swetha, and G. A. Suneetha. "Novel Aryl Ether Derivatives as Antiinflammatory and Analgesics." E-Journal of Chemistry 8, no. 3 (2011): 1401–7. http://dx.doi.org/10.1155/2011/545403.

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The diaryl ether moieties have attracted considerable attention of medicinal chemists as they are endowed with a wide range of diverse biological activities. The present study involves synthesis, characterization of some new aryl ethers and evaluation of their antiinflammatory and analgesic activity. A series of new aryl ether derivatives[4(a-h), 5]were prepared by Ullmann’s ether condensation. The structures of new compounds are supported by their IR,1H NMR and Mass spectra. The new derivatives were evaluated for their antiinflammatory and analgesic activity. Among the tested, compound3has sh

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38

Noorpoor, Zeinab, and Saeed Tavangar. "Preparation and characterization of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in synthesis of diaryl ether by the Ullmann coupling reaction." Journal of Coordination Chemistry 74, no. 9-10 (2021): 1651–62. http://dx.doi.org/10.1080/00958972.2021.1914333.

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39

Schütz, Ramona, Maximilian Meixner, Iris Antes, and Franz Bracher. "A modular approach to the bisbenzylisoquinoline alkaloids tetrandrine and isotetrandrine." Organic & Biomolecular Chemistry 18, no. 16 (2020): 3047–68. http://dx.doi.org/10.1039/d0ob00078g.

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A modular short-step synthesis of the bisbenzylisoquinoline alkaloids tetrandrine and isotetrandrine was developed employing N-acyl-Pictet–Spengler reaction and Ullman diaryl ether synthesis as central steps.

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40

Salih, M. Quamar, and Christopher M. Beaudry. "Enantioselective Ullmann Ether Couplings: Syntheses of (−)-Myricatomentogenin, (−)-Jugcathanin, (+)-Galeon, and (+)-Pterocarine." Organic Letters 15, no. 17 (2013): 4540–43. http://dx.doi.org/10.1021/ol402096k.

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41

Cristau, Henri-Jean, Pascal P. Cellier, Samy Hamada, Jean-Francis Spindler, and Marc Taillefer. "A General and Mild Ullmann-Type Synthesis of Diaryl Ethers." Organic Letters 6, no. 6 (2004): 913–16. http://dx.doi.org/10.1021/ol036290g.

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42

Xiao, Rongshi Li, David Hurst, et al. "Solid-Phase Synthesis of Alkyl Aryl Ethers via the Ullmann Condensation." Journal of Combinatorial Chemistry 4, no. 5 (2002): 536–39. http://dx.doi.org/10.1021/cc020035q.

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43

Naidu, Ajay B., O. R. Raghunath, D. J. C. Prasad, and G. Sekar. "An efficient BINAM–copper(II) catalyzed Ullmann-type synthesis of diaryl ethers." Tetrahedron Letters 49, no. 6 (2008): 1057–61. http://dx.doi.org/10.1016/j.tetlet.2007.11.203.

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44

Qian, Cun-Wei, Wen-Lin Lv, Qian-Shou Zong, Mao-Yuan Wang, and Dong Fang. "Copper-catalyzed Ullmann-type synthesis of diaryl ethers assisted by salicylaldimine ligands." Chinese Chemical Letters 25, no. 2 (2014): 337–40. http://dx.doi.org/10.1016/j.cclet.2013.11.036.

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45

Zhao, Yuanhong, Yunsong Wang, Hongwei Sun, Liang Li, and Hongbin Zhang. "Ullmann reaction in tetraethyl orthosilicate: a novel synthesis of triarylamines and diaryl ethers." Chemical Communications, no. 30 (2007): 3186. http://dx.doi.org/10.1039/b706449g.

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46

Qian, Cunwei, Liang Qin, Qianshou Zong, Lin Wu, and Dong Fang. "Aminophenols as Efficient Ligand for Copper-Catalyzed Ullmann-type Synthesis of Diaryl Ethers." Bulletin of the Korean Chemical Society 34, no. 12 (2013): 3915–18. http://dx.doi.org/10.5012/bkcs.2013.34.12.3915.

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47

Lou, Ya Zhou, Xiao Xia Sun, and Ying Chun Li. "The New Synthesis of Novel Organic Light-Emitting Material Spirobifluorene by Ullman Coupling." Applied Mechanics and Materials 204-208 (October 2012): 4051–54. http://dx.doi.org/10.4028/www.scientific.net/amm.204-208.4051.

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A mide, simple and efficient synthetic procedure for the preparation of 2,7-dibromo-2′,3′,6′,7′-tetra(2-methylbutyloxy)spirobifluorene and key intermediates, tetra(2-methlbutyloxy)biphenyl ，2-bromo-4,5,3′,4′-tetra(2-methylbutyloxy)biphenyl, 2,7-Dibromo-2′,6,3′,7′--tetra(2-methylbutyloxy)biphenyl-9-Fluorenol, has been developed. The procedure described herein offers several advantages, including high product yields, easy purification, and large scale production. Ether protected 2,7-dibromo-9,9′-spirobifluorene has good solubility in organic aolvents to permit an appropriate coating process, abi

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48

Knepper, Kerstin, Matthias E. P. Lormann, and Stefan Bräse. "Efficient Synthesis of Highly Substituted Diaryl Ethers on Solid Supports Using the Ullmann Reaction." Journal of Combinatorial Chemistry 6, no. 4 (2004): 460–63. http://dx.doi.org/10.1021/cc0499688.

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49

Qian, Cun-Wei, Wen-Lin Lv, Qian-Shou Zong, Mao-Yuan Wang, and Dong Fang. "ChemInform Abstract: Copper-Catalyzed Ullmann-Type Synthesis of Diaryl Ethers Assisted by Salicylaldimine Ligands." ChemInform 45, no. 28 (2014): no. http://dx.doi.org/10.1002/chin.201428057.

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50

Smith, Keith, and Dennis Jones. "A superior synthesis of diaryl ethers by the use of ultrasound in the Ullmann reaction." Journal of the Chemical Society, Perkin Transactions 1, no. 4 (1992): 407. http://dx.doi.org/10.1039/p19920000407.

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