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Journal articles on the topic 'Decarboxylative arylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Patra, Tuhin, Sudip Nandi, Santosh K. Sahoo, and Debabrata Maiti. "Copper mediated decarboxylative direct C–H arylation of heteroarenes with benzoic acids." Chemical Communications 52, no. 7 (2016): 1432–35. http://dx.doi.org/10.1039/c5cc08367b.

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Copper mediated decarboxylative direct C–H arylation of 5-membered heteroarenes with aryl carboxylic acids is developed using the molecular oxygen as sole oxidant. Copper plays the dual role in decarboxylation and C–H arylation.

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2

Figliola, Carlotta, Sarah M. Greening, Connor Lamont, Brandon R. Groves, and Alison Thompson. "Decarboxylative arylation of substituted pyrroles N-protected with 2-(trimethylsilyl)ethoxymethyl (SEM)." Canadian Journal of Chemistry 96, no. 6 (June 2018): 534–42. http://dx.doi.org/10.1139/cjc-2017-0402.

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Palladium-catalyzed decarboxylative arylation is reported using pyrroles N-protected with the 2-(trimethylsilyl)ethoxymethyl (SEM) group and featuring 2-, 3-, and 4-substituents about the pyrrolic framework. In contrast to N-protected pyrroles previously used in decarboxylative arylation, the use of SEM allows deprotection under mild conditions.

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3

Li, Dengke, Ning Xu, Yicheng Zhang, and Lei Wang. "A highly efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides." Chem. Commun. 50, no. 94 (2014): 14862–65. http://dx.doi.org/10.1039/c4cc06457g.

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4

Recio, III, Antonio, Jeffrey D. Heinzman, and Jon A. Tunge. "Decarboxylative benzylation and arylation of nitriles." Chem. Commun. 48, no. 1 (2012): 142–44. http://dx.doi.org/10.1039/c1cc16011g.

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5

Chen, Lijun, Lin Ju, Katelyn A. Bustin, and Jessica M. Hoover. "Copper-catalyzed oxidative decarboxylative C–H arylation of benzoxazoles with 2-nitrobenzoic acids." Chemical Communications 51, no. 81 (2015): 15059–62. http://dx.doi.org/10.1039/c5cc06645j.

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6

Li, Huan, Lei Guo, Xiaoliang Feng, Liping Huo, Shengqing Zhu, and Lingling Chu. "Sequential C–O decarboxylative vinylation/C–H arylation of cyclic oxalates via a nickel-catalyzed multicomponent radical cascade." Chemical Science 11, no. 19 (2020): 4904–10. http://dx.doi.org/10.1039/d0sc01471k.

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7

Karale, Uttam B., Saradhi Kalari, Jala Shivakumar, Vitthal B. Makane, Dattatraya A. Babar, Ritesh P. Thakare, Bathini Nagendra Babu, Sidharth Chopra, and Haridas B. Rode. "Ligand-free Pd-catalysed decarboxylative arylation of imidazo[1,2-a]pyridine-3-carboxylic acids with aryl bromides." RSC Advances 6, no. 69 (2016): 65095–104. http://dx.doi.org/10.1039/c6ra12166g.

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8

Mu, Bing, Yusheng Wu, Jingya Li, Dapeng Zou, Junbiao Chang, and Yangjie Wu. "An unprecedented Pd-catalyzed decarboxylative coupling reaction of aromatic carboxylic acids in aqueous medium under air: synthesis of 3-aryl-imidazo[1,2-a]pyridines from aryl chlorides." Organic & Biomolecular Chemistry 14, no. 1 (2016): 246–50. http://dx.doi.org/10.1039/c5ob02112j.

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9

Mendis, Shehani N., and Jon A. Tunge. "Decarboxylative dearomatization and mono-α-arylation of ketones." Chemical Communications 52, no. 49 (2016): 7695–98. http://dx.doi.org/10.1039/c6cc03672d.

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10

Crawford, Jennifer M., Kyle E. Shelton, Emily K. Reeves, Bryce K. Sadarananda, and Dipannita Kalyani. "Nickel-catalyzed decarboxylative arylation of azoles with perfluoro- and nitrobenzoates." Organic Chemistry Frontiers 2, no. 6 (2015): 726–29. http://dx.doi.org/10.1039/c5qo00040h.

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11

Recio, Antonio III, Jeffrey D. Heinzman, and Jon A. Tunge. "ChemInform Abstract: Decarboxylative Benzylation and Arylation of Nitriles." ChemInform 43, no. 18 (April 5, 2012): no. http://dx.doi.org/10.1002/chin.201218107.

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12

Sun, Meng, Zhe Wang, Jiaxin Wang, Peiyu Guo, Xiangxiang Chen, and Ya-Min Li. "Palladium-catalyzed decarboxylative ortho-arylation of 2-pyridyl sulfoxides with benzoyl peroxides." Organic & Biomolecular Chemistry 14, no. 45 (2016): 10585–88. http://dx.doi.org/10.1039/c6ob02040b.

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13

Zhang, Yan, Zhe-Yao Hu, Xin-Chang Li, and Xun-Xiang Guo. "Copper-Catalyzed Decarboxylative N-Arylation of Indole-2-carboxylic Acids." Synthesis 51, no. 08 (January 10, 2019): 1803–8. http://dx.doi.org/10.1055/s-0037-1611946.

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A novel decarboxylative N-arylation of indole-2-carboxylic acids with aryl halides is developed. The reaction proceeds efficiently in the presence of Cu2O as the catalyst to give the corresponding N-aryl indoles in high yields. This synthetic method shows good functional group tolerance and offers an alternative route to construct N-aryl indoles.

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14

Zhang, Yun, Sejal Patel, and Nello Mainolfi. "Copper-catalyzed decarboxylative C–N coupling for N-arylation." Chemical Science 3, no. 11 (2012): 3196. http://dx.doi.org/10.1039/c2sc20606d.

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15

Pei, Kai, Xiaoming Jie, Huaiqing Zhao, and Weiping Su. "Palladium-Catalyzed Decarboxylative C-H Bond Arylation of Furans." European Journal of Organic Chemistry 2014, no. 20 (June 5, 2014): 4230–33. http://dx.doi.org/10.1002/ejoc.201402278.

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16

Hu, Peng, Min Zhang, Xiaoming Jie, and Weiping Su. "Palladium-Catalyzed Decarboxylative CH Bond Arylation of Thiophenes." Angewandte Chemie 124, no. 1 (November 15, 2011): 231–35. http://dx.doi.org/10.1002/ange.201106451.

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17

Hu, Peng, Min Zhang, Xiaoming Jie, and Weiping Su. "Palladium-Catalyzed Decarboxylative CH Bond Arylation of Thiophenes." Angewandte Chemie International Edition 51, no. 1 (November 15, 2011): 227–31. http://dx.doi.org/10.1002/anie.201106451.

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18

Ghorbani-Choghamarani, Arash, and Zahra Taherinia. "High Catalytic Activity of Peptide Nanofibres Decorated with Ni and Cu Nanoparticles for the Synthesis of 5-Substituted 1H-Tetrazoles and N-Arylation of Amines." Australian Journal of Chemistry 70, no. 10 (2017): 1127. http://dx.doi.org/10.1071/ch17176.

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A rapid development of a new methodology for decarboxylative N-arylation of carboxylic acids and the preparation of 5-substituted 1H-tetrazoles catalysed by peptide nanofibres decorated with Cu and Ni nanoparticles is presented. Compared with conventional aryl halides, benzoic acids are extremely interesting and environmentally friendly options for the synthesis of secondary aryl amines.

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19

Johnson, Tarn C., and Stephen P. Marsden. "A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines." Beilstein Journal of Organic Chemistry 12 (January 4, 2016): 1–4. http://dx.doi.org/10.3762/bjoc.12.1.

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A convenient, one-pot, two-component synthesis of 2-(1-amidoalkyl)pyridines is reported, based upon the substitution of suitably-activated pyridine N-oxides by azlactone nucleophiles, followed by decarboxylative azlactone ring-opening. The synthesis obviates the need for precious metal catalysts to achieve a formal enolate arylation reaction, and constitutes a formally ‘umpoled’ approach to this valuable class of bioactive structures.

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20

Fu, Haiyan, Hua Chen, and Henri Doucet. "Palladium-catalyzed selective decarboxylative coupling reaction versus direct C―H arylation for arylation of heteroaromatics." Applied Organometallic Chemistry 27, no. 10 (August 23, 2013): 595–600. http://dx.doi.org/10.1002/aoc.3037.

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21

Moon, Patrick J., Shengkang Yin, and Rylan J. Lundgren. "Ambient Decarboxylative Arylation of Malonate Half-Esters via Oxidative Catalysis." Journal of the American Chemical Society 138, no. 42 (October 17, 2016): 13826–29. http://dx.doi.org/10.1021/jacs.6b08906.

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22

Ni, Shengyang, Yu Zhang, Chen Xie, Haibo Mei, Jianlin Han, and Yi Pan. "Oxidative Difunctionalization of Alkynoates through Alkylation and Migration Decarboxylative Arylation." Organic Letters 17, no. 22 (October 30, 2015): 5524–27. http://dx.doi.org/10.1021/acs.orglett.5b02356.

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23

Yang, Ke, Peng Wang, Cheng Zhang, Adnan A. Kadi, Hoong-Kun Fun, Yan Zhang, and Hongjian Lu. "Nickel-Catalyzed Decarboxylative Arylation of Heteroarenes through sp2C-H Functionalization." European Journal of Organic Chemistry 2014, no. 34 (October 21, 2014): 7586–89. http://dx.doi.org/10.1002/ejoc.201403234.

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24

Seo, Sangwon, Mark Slater, and Michael F. Greaney. "Decarboxylative C–H Arylation of Benzoic Acids under Radical Conditions." Organic Letters 14, no. 10 (May 9, 2012): 2650–53. http://dx.doi.org/10.1021/ol3010694.

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25

Singh, Keisham. "Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts." Catalysts 9, no. 2 (February 12, 2019): 173. http://dx.doi.org/10.3390/catal9020173.

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The past decades have witnessed rapid development in organic synthesis via catalysis, particularly the reactions through C–H bond functionalization. Transition metals such as Pd, Rh and Ru constitute a crucial catalyst in these C–H bond functionalization reactions. This process is highly attractive not only because it saves reaction time and reduces waste,but also, more importantly, it allows the reaction to be performed in a highly region specific manner. Indeed, several organic compounds could be readily accessed via C–H bond functionalization with transition metals. In the recent past, tremendous progress has been made on C–H bond functionalization via ruthenium catalysis, including less expensive but more stable ruthenium(II) catalysts. The ruthenium-catalysed C–H bond functionalization, viz. arylation, alkenylation, annulation, oxygenation, and halogenation involving C–C, C–O, C–N, and C–X bond forming reactions, has been described and presented in numerous reviews. This review discusses the recent development of C–H bond functionalization with various ruthenium-based catalysts. The first section of the review presents arylation reactions covering arylation directed by N–Heteroaryl groups, oxidative arylation, dehydrative arylation and arylation involving decarboxylative and sp3-C–H bond functionalization. Subsequently, the ruthenium-catalysed alkenylation, alkylation, allylation including oxidative alkenylation and meta-selective C–H bond alkylation has been presented. Finally, the oxidative annulation of various arenes with alkynes involving C–H/O–H or C–H/N–H bond cleavage reactions has been discussed.

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26

Nandi, Debkumar, Yang-Ming Jhou, Jhen-Yi Lee, Bing-Chiuan Kuo, Chien-Yu Liu, Pei-Wen Huang, and Hon Man Lee. "Pd(0)-Catalyzed Decarboxylative Coupling and Tandem C–H Arylation/Decarboxylation for the Synthesis of Heteroaromatic Biaryls." Journal of Organic Chemistry 77, no. 20 (October 2, 2012): 9384–90. http://dx.doi.org/10.1021/jo3015837.

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27

Kölmel, Dominik K., Jiang Meng, Mei-Hsuan Tsai, Jiamin Que, Richard P. Loach, Thomas Knauber, Jinqiao Wan, and Mark E. Flanagan. "On-DNA Decarboxylative Arylation: Merging Photoredox with Nickel Catalysis in Water." ACS Combinatorial Science 21, no. 8 (June 21, 2019): 588–97. http://dx.doi.org/10.1021/acscombsci.9b00076.

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28

Yu, Wing-Yiu, Wing Nga Sit, Zhongyuan Zhou, and Albert S. C. Chan. "Palladium-Catalyzed Decarboxylative Arylation of C−H Bonds by Aryl Acylperoxides." Organic Letters 11, no. 15 (August 6, 2009): 3174–77. http://dx.doi.org/10.1021/ol900756g.

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29

Cornella, Josep, Pengfei Lu, and Igor Larrosa. "Intermolecular Decarboxylative Direct C-3 Arylation of Indoles with Benzoic Acids." Organic Letters 11, no. 23 (December 3, 2009): 5506–9. http://dx.doi.org/10.1021/ol902304n.

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30

Hu, Peng, Min Zhang, Xiaoming Jie, and Weiping Su. "ChemInform Abstract: Palladium-Catalyzed Decarboxylative C-H Bond Arylation of Thiophenes." ChemInform 43, no. 19 (April 12, 2012): no. http://dx.doi.org/10.1002/chin.201219108.

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31

Pei, Kai, Xiaoming Jie, Huaiqing Zhao, and Weiping Su. "ChemInform Abstract: Palladium-Catalyzed Decarboxylative C-H Bond Arylation of Furans." ChemInform 46, no. 8 (February 2015): no. http://dx.doi.org/10.1002/chin.201508162.

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32

Zhang, Yun, Sejal Patel, and Nello Mainolfi. "ChemInform Abstract: Copper-Catalyzed Decarboxylative C-N Coupling for N-Arylation." ChemInform 44, no. 12 (March 14, 2013): no. http://dx.doi.org/10.1002/chin.201312029.

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33

Fu, Haiyan, Hua Chen, and Henri Doucet. "ChemInform Abstract: Palladium-Catalyzed Selective Decarboxylative Coupling Reaction versus Direct C-H Arylation for Arylation of Heteroaromatics." ChemInform 45, no. 9 (February 14, 2014): no. http://dx.doi.org/10.1002/chin.201409117.

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34

Yang, Ke, Peng Wang, Cheng Zhang, Adnan A. Kadi, Hoong-Kun Fun, Yan Zhang, and Hongjian Lu. "ChemInform Abstract: Nickel-Catalyzed Decarboxylative Arylation of Heteroarenes Through sp2C-H Functionalization." ChemInform 46, no. 17 (April 2015): no. http://dx.doi.org/10.1002/chin.201517180.

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35

Crawford, Jennifer M., Kyle E. Shelton, Emily K. Reeves, Bryce K. Sadarananda, and Dipannita Kalyani. "ChemInform Abstract: Nickel-Catalyzed Decarboxylative Arylation of Azoles with Perfluoro- and Nitrobenzoates." ChemInform 46, no. 38 (September 2015): no. http://dx.doi.org/10.1002/chin.201538148.

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36

Carrër, Amandine, Jean-Daniel Brion, Samir Messaoudi, and Mouad Alami. "Synthesis of 3,4-Disubstituted Quinolin-2-(1H)-onesviaPalladium-Catalyzed Decarboxylative Arylation Reactions." Advanced Synthesis & Catalysis 355, no. 10 (July 8, 2013): 2044–54. http://dx.doi.org/10.1002/adsc.201300299.

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37

Seo, Sangwon, Mark Slater, and Michael F. Greaney. "ChemInform Abstract: Decarboxylative C-H Arylation of Benzoic Acids under Radical Conditions." ChemInform 43, no. 37 (August 16, 2012): no. http://dx.doi.org/10.1002/chin.201237085.

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38

Scheipers, Ina, Christian Mück‐Lichtenfeld, and Armido Studer. "Palladium‐Catalyzed Decarboxylative γ‐Arylation for the Synthesis of Tetrasubstituted Chiral Allenes." Angewandte Chemie International Edition 58, no. 20 (May 13, 2019): 6545–48. http://dx.doi.org/10.1002/anie.201901848.

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39

Unoh, Yuto, Koji Hirano, Tetsuya Satoh, and Masahiro Miura. "Palladium-Catalyzed Decarboxylative Arylation of Benzoylacrylic Acids toward the Synthesis of Chalcones." Journal of Organic Chemistry 78, no. 10 (May 6, 2013): 5096–102. http://dx.doi.org/10.1021/jo400716e.

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40

Gigant, Nicolas, Laëtitia Chausset-Boissarie, and Isabelle Gillaizeau. "Direct Site-Selective Arylation of Enamides via a Decarboxylative Cross-Coupling Reaction." Organic Letters 15, no. 4 (January 31, 2013): 816–19. http://dx.doi.org/10.1021/ol303497q.

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41

Nandi, Debkumar, Yang-Ming Jhou, Jhen-Yi Lee, Bing-Chiuan Kuo, Chien-Yu Liu, Pei-Wen Huang, and Hon Man Lee. "ChemInform Abstract: Pd(0)-Catalyzed Decarboxylative Coupling and Tandem C-H Arylation/Decarboxylation for the Synthesis of Heteroaromatic Biaryls." ChemInform 44, no. 7 (February 12, 2013): no. http://dx.doi.org/10.1002/chin.201307092.

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42

Scheipers, Ina, Eva Koch, and Armido Studer. "Stereoselective Palladium-Catalyzed Decarboxylative γ-Arylation of Acyclic β,γ-Unsaturated Carboxylic Acids." Organic Letters 19, no. 7 (March 23, 2017): 1741–43. http://dx.doi.org/10.1021/acs.orglett.7b00512.

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43

Xie, Kai, Zhiyong Yang, Xingjian Zhou, Xiujian Li, Sizhuo Wang, Ze Tan, Xiangyu An, and Can-Cheng Guo. "Pd-Catalyzed Decarboxylative Arylation of Thiazole, Benzoxazole, and Polyfluorobenzene with Substituted Benzoic Acids." Organic Letters 12, no. 7 (April 2, 2010): 1564–67. http://dx.doi.org/10.1021/ol100296b.

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44

Yu, Wing-Yiu, Wing Nga Sit, Zhongyuan Zhou, and Albert S. C. Chan. "ChemInform Abstract: Palladium-Catalyzed Decarboxylative Arylation of C-H Bonds by Aryl Acylperoxides." ChemInform 40, no. 48 (November 6, 2009): no. http://dx.doi.org/10.1002/chin.200948093.

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45

Hachem, Mahmoud, Cédric Schneider, and Christophe Hoarau. "Direct Stereoselective β-Arylation of Enol Ethers by a Decarboxylative Heck-Type Reaction." European Journal of Organic Chemistry 2020, no. 14 (March 30, 2020): 2052–61. http://dx.doi.org/10.1002/ejoc.201901877.

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46

Shintani, Ryo, Takaoki Tsuji, Soyoung Park, and Tamio Hayashi. "Palladium-catalyzed intramolecular decarboxylative allylic arylation of α-aryl-γ-methylidene-δ-valerolactones." Chemical Communications 46, no. 10 (2010): 1697. http://dx.doi.org/10.1039/b924416f.

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47

Gu, Zhenhua, Kun Zhao, and Linlin Ding. "Development of New Electrophiles in Palladium/Norbornene-Catalyzed ortho-Functionalization of Aryl Halides." Synlett 30, no. 02 (October 2, 2018): 129–40. http://dx.doi.org/10.1055/s-0037-1611057.

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This account focuses on our work in palladium/norbornene-catalyzed selective ortho-arylation and ortho-acylation of aryl halides. It will discuss our synthetic plan, initial design and revised strategy in the enantioselective synthesis of the rhazinal family of natural products. It also shows our efforts on the α-acylation reaction by the cleavage of various C(O)–X bonds, along with some mechanistic studies.1 Introduction2 Synthesis of the Rhazinal Family of Natural Products2.1 Initial Design2.2 Revised Strategy2.3 Enantioselective Synthesis of the Rhazinal Family of Natural Products3 Catalytic ortho-Acylation3.1 Acid Chloride and Anhydride Strategy3.2 Cleavage of C(O)–S Bond of Thioesters by Pd, Norbornene and Copper Cocatalysis4 Decarboxylative Alkynylation5 Conclusion

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48

Chen, Junmin, Qiuhong Wang, Xiangkang Li, and Yongli Zhao. "Silver-catalyzed intramolecular oxidative decarboxylative C-H arylation reactions for synthesis of biaryl sultams." Arkivoc 2019, no. 6 (September 8, 2019): 105–15. http://dx.doi.org/10.24820/ark.5550190.p010.846.

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49

Zhang, Xitao, Xiujuan Feng, Chuancheng Zhou, Xiaoqiang Yu, Yoshinori Yamamoto, and Ming Bao. "Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions." Organic Letters 20, no. 22 (November 2, 2018): 7095–99. http://dx.doi.org/10.1021/acs.orglett.8b03043.

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50

Unoh, Yuto, Koji Hirano, Tetsuya Satoh, and Masahiro Miura. "ChemInform Abstract: Palladium-Catalyzed Decarboxylative Arylation of Benzoylacrylic Acids Toward the Synthesis of Chalcones." ChemInform 44, no. 37 (August 22, 2013): no. http://dx.doi.org/10.1002/chin.201337077.

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