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Journal articles on the topic 'Friedel-Crafts acylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Đud, Mateja, Anamarija Briš, Iva Jušinski, Davor Gracin, and Davor Margetić. "Mechanochemical Friedel–Crafts acylations." Beilstein Journal of Organic Chemistry 15 (June 17, 2019): 1313–20. http://dx.doi.org/10.3762/bjoc.15.130.

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Friedel–Crafts (FC) acylation reactions were exploited in the preparation of ketone-functionalized aromatics. Environmentally more friendly, solvent-free mechanochemical reaction conditions of this industrially important reaction were developed. Reaction parameters such as FC catalyst, time, ratio of reagents and milling support were studied to establish the optimal reaction conditions. The scope of the reaction was explored by employment of different aromatic hydrocarbons in conjunction with anhydrides and acylation reagents. It was shown that certain FC-reactive aromatics could be effectively functionalized by FC acylations carried out under ball-milling conditions without the presence of a solvent. The reaction mechanism was studied by in situ Raman and ex situ IR spectroscopy.

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2

Tran, Phuong Hoang, Thanh Duy Anh Nguyen, and Thach Ngoc Le. "Friedel-crafts acylation of aromatic compounds using Triflat bismuth." Science and Technology Development Journal 17, no. 2 (June 30, 2014): 10–14. http://dx.doi.org/10.32508/stdj.v17i2.1310.

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Friedel-Crafts acylation of aromatic compounds with acetic anhydride as acylating reagent was investigated in the presence of Lewis acid. Bismuth trifluoromethanesulfonate was found to be efficient catalyst for Friedel-Crafts acetylation under mild conditions. Bismuth triflate is safe-to-handle, simple and clean work-up, good yield and short reaction time

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3

Toma, Štefan, and Marta Sališová. "Acylation of ω-phenylalkanoylferrocenes by cinnamoyl and phenylpropiolyl chlorides." Collection of Czechoslovak Chemical Communications 52, no. 6 (1987): 1520–26. http://dx.doi.org/10.1135/cccc19871520.

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In Friedel-Crafts acylation of ω-phenylalkanoylferrocenes, the site of electrophilic attack depends on the reagent used. The acylation with cinnamoyl chloride yields preferentially the products of substitution of the unsubstituted cyclopentadienyl ring of ferrocene. The acylation with phenylpropionyl chloride affords the products of acylation of the benzene ring of the starting compound. The different behaviour of both acylating agents is discussed.

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4

Esteban, Gema, Rocío Rincón, Aurelio G. Csákÿ, and Joaquín Plumet. "A Convenient Synthesis of the Central Core of Helioporins, seco-Pseudopterosins and Pseudopterosins via BCA-Annulation Sequence." Natural Product Communications 3, no. 4 (April 2008): 1934578X0800300. http://dx.doi.org/10.1177/1934578x0800300405.

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A convenient synthesis of the central core of helioporins, seco-pseudopterosins and pseudopterosins in racemic form is reported, using a Suzuki coupling (A-ring formation)-Friedel-Crafts acylation sequence, followed by synthetic elaboration of the resulting tetralone derivative. Key steps of the method are a totally diastereoselective cuprate conjugate addition and a final, spontaneous Friedel-Crafts acylation.

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5

Metivier, Pascal. "ChemInform Abstract: Friedel-Crafts Acylation." ChemInform 33, no. 41 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200241266.

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6

Chua, Chun Kiang, and Martin Pumera. "Friedel-Crafts Acylation on Graphene." Chemistry - An Asian Journal 7, no. 5 (March 13, 2012): 1009–12. http://dx.doi.org/10.1002/asia.201200096.

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7

Raja, Erum K., Daniel J. DeSchepper, Sten O. Nilsson Lill, and Douglas A. Klumpp. "Friedel–Crafts Acylation with Amides." Journal of Organic Chemistry 77, no. 13 (June 21, 2012): 5788–93. http://dx.doi.org/10.1021/jo300922p.

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8

Lan, Kun, Shao Fen, and Zixing Shan. "Synthesis of Aromatic Cycloketones via Intramolecular Friedel - Crafts Acylation Catalyzed by Heteropoly Acids." Australian Journal of Chemistry 60, no. 1 (2007): 80. http://dx.doi.org/10.1071/ch06277.

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Under liquid-phase conditions, the intramolecular Friedel–Crafts acylation of aryl benzoic acids catalyzed by heteropoly acids were investigated for the first time. Several aryl benzoic acids were refluxed and dehydrated in chlorobenzene in the presence of 0.2 equivalents of a heteropoly acid, and anthraquinone, anthrone, and xanthone were obtained in good yield. At the same time, an intermolecular Friedel–Crafts acylation and decarboxylation reaction were observed in this experiment.

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9

Jadhav, Arvind H., Amutha Chinnappan, Vishwanath Hiremath, and Jeong Gil Seo. "Synthesis and Characterization of AlCl3 Impregnated Molybdenum Oxide as Heterogeneous Nano-Catalyst for the Friedel-Crafts Acylation Reaction in Ambient Condition." Journal of Nanoscience and Nanotechnology 15, no. 10 (October 1, 2015): 8243–50. http://dx.doi.org/10.1166/jnn.2015.11253.

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Aluminum trichloride (AlCl3) impregnated molybdenum oxide heterogeneous nano-catalyst was prepared by using simple impregnation method. The prepared heterogeneous catalyst was characterized by powder X-ray diffraction, FT-IR spectroscopy, solid-state NMR spectroscopy, SEM imaging, and EDX mapping. The catalytic activity of this protocol was evaluated as heterogeneous catalyst for the Friedel-Crafts acylation reaction at room temperature. The impregnated MoO4(AlCl2)2 catalyst showed tremendous catalytic activity in Friedel-Crafts acylation reaction under solvent-free and mild reaction condition. As a result, 84.0% yield of acyl product with 100% consumption of reactants in 18 h reaction time at room temperature was achieved. The effects of different solvents system with MoO4(AlCl2)2 catalyst in acylation reaction was also investigated. By using optimized reaction condition various acylated derivatives were prepared. In addition, the catalyst was separated by simple filtration process after the reaction and reused several times. Therefore, heterogeneous MoO4(AlCl2)2 catalyst was found environmentally benign catalyst, very convenient, high yielding, and clean method for the Friedel-Crafts acylation reaction under solvent-free and ambient reaction condition.

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10

Tran, Phuong Hoang, Vy Hieu Huynh, Hai Ngoc Tran, and Thach Ngoc Le. "Microwave-assisted intramolecular FriedelCrafts acylation of some aryl aliphatic acids using Gd(OTf)3/ [BMI]BF4 catalytic system." Science and Technology Development Journal 19, no. 2 (June 30, 2016): 64–70. http://dx.doi.org/10.32508/stdj.v19i2.803.

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Intramolecular Friedel–Crafts acylation of aryl acids is a “green” reaction and environmentally benign, generates some valuable intermediated compounds for pharmaceutical uses. In addition, metal triflates under microwave irradiation are efficient catalysts, solving many problems when using traditional Lewis acids. Gd(OTf)3/[BMI]BF4, a good catalyst for the intramolecular Friedel–Crafts acylation under mild condition with high yield, reduced the reaction time and pollution. Furthermore, Gd(OTf)3 in [BMI]BF4 was easily recovered and reused without significant loss of its activity

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11

Nandi, Kartik Kumar. "SUSTAINABLE CATALYST FOR FRIEDEL–CRAFTS ACYLATION." Catalysis in Green Chemistry and Engineering 1, no. 2 (2018): 149–53. http://dx.doi.org/10.1615/.2018021112.

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12

Chavan, Subhash P., Sumanta Garai, Achintya Kumar Dutta, and Sourav Pal. "Friedel-Crafts Acylation Reactions Using Esters." European Journal of Organic Chemistry 2012, no. 35 (November 6, 2012): 6841–45. http://dx.doi.org/10.1002/ejoc.201201181.

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13

Agee, Brian M., Gene Mullins, and Daniel J. Swartling. "Friedel–Crafts Acylation Using Solar Irradiation." ACS Sustainable Chemistry & Engineering 1, no. 12 (September 13, 2013): 1580–83. http://dx.doi.org/10.1021/sc4002802.

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14

Wei, Ben Mei, Zhi Yong Zhang, and Zhi Qun Dai. "Friedel-Crafts Acylation of Anisole Catalyzed by Green, Reusable Hydroxyapatite-Zinc Bromide Catalyst." Advanced Materials Research 113-116 (June 2010): 18–21. http://dx.doi.org/10.4028/www.scientific.net/amr.113-116.18.

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This study was aimed at the development of a green and reusable catalyst for Friedel-Crafts acylation. Firstly, Hydroxyapatite (HAP) and Hydroxyapatite-zinc bromide (HAP-ZnBr2) have been prepared by the co-precipatation method and hydrothermal method respectively. Their structures were characterized by X-ray Diffraction (XRD), Brunauer-Emmett-Teller (BET) and Infrared Spectroscopy (IR). The catalytic efficiency of HAP-ZnBr2 was examined for Friedel-Crafts acylation of anisole. The results showed that the catalyst was green, high activity, high selectivity and it could be reused at least 5 times without obvious activity loss.

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15

Chen, Yong, Jun Qian, Qi Xin Zhuang, and Zhe Wen Han. "The Preparation and Characterization of Polybenzoxazole Copolymerized with Multiwalled Carbon Nanotube via Direct Friedel-Crafts Acylation." Advanced Materials Research 989-994 (July 2014): 560–63. http://dx.doi.org/10.4028/www.scientific.net/amr.989-994.560.

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Multiwalled carbon nanotube (MWCNT) was subjected a copolymerization reaction with 4, 6-diaminoresorcinol salt (DAR•2HCl) and terephthalic acid (TA) in polyphosphoric acid (PPA) by Friedel-Crafts acylation reaction without any acid treatment or modification. The structure and morphology of the as-prepared poly (p-phenylene benzobisoxazole) (PBO)/MWCNT nanocomposites were characterized by X-ray diffraction (XRD) and scanning electronic microscope (SEM). The SEM images indicated that MWCNTs can disperse in PBO matrix uniformly without agglomeration and MWCNTs have been introduced into PBO matrix by covalent bonding via Friedel-Crafts acylation between MWCNTs and TA.

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16

Satyanarayana, Gedu, and Basuli Suchand. "Palladium-Catalyzed Direct Acylation: One-Pot Relay Synthesis of Anthraquinones." Synthesis 51, no. 03 (October 10, 2018): 769–79. http://dx.doi.org/10.1055/s-0037-1610296.

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A bis-acylation strategy to access functionalized anthraquinones via one-pot relay process, is presented. The first acylation was feasible under [Pd]-catalyzed intermolecular direct acylation reaction, while, the second acylation was accomplished by using intramolecular Friedel–Crafts acylation. Notably, benchtop aldehydes have been utilized as non-toxic acylation agents in the key [Pd]-catalyzed acylation.

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17

Nayak, Yogeesha N., Swarnagowri Nayak, Y. F. Nadaf, Nitinkumar S. Shetty, and Santosh L. Gaonkar. "Zeolite Catalyzed Friedel-Crafts Reactions: A Review." Letters in Organic Chemistry 17, no. 7 (July 7, 2020): 491–506. http://dx.doi.org/10.2174/1570178616666190807101012.

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Friedel-Crafts reaction is one of the most useful synthetic tools in organic chemistry, mainly in the synthesis of aromatic ketones. The active catalysts for this reaction are modified zeolites and are preferable catalysts when shape selectivity affects the formation of the expected product. In this review, our aim is to corroborate recent literature available on zeolite catalyzed Friedel-Crafts alkylation and acylation reaction.

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18

Yang, Qiong, Wenyao Wang, Yanxi Zhao, Junjiang Zhu, Yujun Zhu, and Lihua Wang. "Metal-free mesoporous carbon nitride catalyze the Friedel–Crafts reaction by activation of benzene." RSC Advances 5, no. 68 (2015): 54978–84. http://dx.doi.org/10.1039/c5ra08871b.

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19

Jheng, Li-Cheng, Afira Ainur Rosidah, Steve Lien-Chung Hsu, Ko-Shan Ho, Chun-Jern Pan, and Cheng-Wei Cheng. "Nanocomposite membranes of polybenzimidazole and amine-functionalized carbon nanofibers for high temperature proton exchange membrane fuel cells." RSC Advances 11, no. 17 (2021): 9964–76. http://dx.doi.org/10.1039/d0ra09972d.

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20

Li, Lian-Hua, Zhi-Jie Niu, and Yong-Min Liang. "New Friedel–Crafts strategy for preparing 3-acylindoles." Organic & Biomolecular Chemistry 16, no. 42 (2018): 7792–96. http://dx.doi.org/10.1039/c8ob02094a.

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21

Chen, Wangqiao, Si Yu Tan, Yanli Zhao, and Qichun Zhang. "A concise method to prepare novel fused heteroaromatic diones through double Friedel–Crafts acylation." Org. Chem. Front. 1, no. 4 (2014): 391–94. http://dx.doi.org/10.1039/c4qo00032c.

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22

Matsumoto, Kazuya, Takayuki Ogawa, and Mitsutoshi Jikei. "Nonstoichiometric polycondensation based on Friedel–Crafts acylation in superacids for the syntheses of aromatic polyketones." Polymer Chemistry 8, no. 47 (2017): 7297–300. http://dx.doi.org/10.1039/c7py01609c.

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23

Quiles-Díaz, Susana, Gerardo Martínez, Marián A. Gómez-Fatou, Gary J. Ellis, and Horacio J. Salavagione. "Anhydride-based chemistry on graphene for advanced polymeric materials." RSC Advances 6, no. 43 (2016): 36656–60. http://dx.doi.org/10.1039/c6ra05498f.

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24

Ghosh, Arun K., Hannah M. Simpson, and Anne M. Veitschegger. "Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction." Organic & Biomolecular Chemistry 16, no. 33 (2018): 5979–86. http://dx.doi.org/10.1039/c8ob01529e.

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25

Song, Hao, Yao Gao, Weili Li, Hongkun Tian, Donghang Yan, Yanhou Geng, and Fosong Wang. "Synthesis and characterization of diketopyrrolopyrrole-based conjugated molecules flanked by indenothiophene and benzoindenothiophene derivatives." Journal of Materials Chemistry C 3, no. 42 (2015): 11135–43. http://dx.doi.org/10.1039/c5tc02288f.

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26

Liu, Yongmei, Guangrong Meng, Ruzhang Liu, and Michal Szostak. "Sterically-controlled intermolecular Friedel–Crafts acylation with twisted amides via selective N–C cleavage under mild conditions." Chemical Communications 52, no. 41 (2016): 6841–44. http://dx.doi.org/10.1039/c6cc02324j.

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27

Song, Hao, Yunfeng Deng, Yu Jiang, Hongkun Tian, and Yanhou Geng. "π-Conjugation expanded isoindigo derivatives and the donor–acceptor conjugated polymers: synthesis and characterization." Chemical Communications 54, no. 7 (2018): 782–85. http://dx.doi.org/10.1039/c7cc08603b.

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28

Wu, Shanchao, Na Liu, Guoqiang Dong, Lin Ma, Shengzheng Wang, Wencai Shi, Kun Fang, et al. "Facile construction of pyrrolo[1,2-b]isoquinolin-10(5H)-ones via a redox-amination–aromatization–Friedel–Crafts acylation cascade reaction and discovery of novel topoisomerase inhibitors." Chemical Communications 52, no. 61 (2016): 9593–96. http://dx.doi.org/10.1039/c6cc03071h.

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29

Pelkey, Erin T., and Gordon W. Gribble. "Novel electrophilic ipso acylation - detosylation reaction of pyrroles." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1338–42. http://dx.doi.org/10.1139/v06-075.

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A pyrrole and two pyrroloindoles that are substituted with a p-toluenesulfonyl group undergo an ipso acylation – detosylation reaction with acid chlorides and aluminum chloride to afford the corresponding acyl-substituted pyrroles and pyrroloindoles.Key words: pyrrole, pyrroloindole, ipso acylation, detosylation, Friedel–Crafts reaction.

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30

Kawamura, Masato, Dong-Mei Cui, and Shigeru Shimada. "Friedel–Crafts acylation reaction using carboxylic acids as acylating agents." Tetrahedron 62, no. 39 (September 2006): 9201–9. http://dx.doi.org/10.1016/j.tet.2006.07.031.

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31

Baba, A., Y. Nishimoto, S. Babu, and M. Yasuda. "Indium-Catalyzed Friedel-Crafts Acylation Using Esters as Acylating Reagents." Synfacts 2009, no. 03 (February 19, 2009): 0313. http://dx.doi.org/10.1055/s-0028-1087711.

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32

Yadav, G. D., and A. A. Pujari. "Friedel–Crafts acylation using sulfated zirconia catalyst." Green Chemistry 1, no. 2 (1999): 69–74. http://dx.doi.org/10.1039/a808891h.

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33

Kaur, J., K. Griffin, B. Harrison, and I. V. Kozhevnikov. "Friedel–Crafts Acylation Catalysed by Heteropoly Acids." Journal of Catalysis 208, no. 2 (June 2002): 448–55. http://dx.doi.org/10.1006/jcat.2002.3592.

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34

Schmidt, Nina G., Tea Pavkov-Keller, Nina Richter, Birgit Wiltschi, Karl Gruber, and Wolfgang Kroutil. "Biocatalytic Friedel-Crafts Acylation and Fries Reaction." Angewandte Chemie International Edition 56, no. 26 (May 23, 2017): 7615–19. http://dx.doi.org/10.1002/anie.201703270.

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35

Raja, Erum K., Daniel J. DeSchepper, Sten O. Nilsson Lill, and Douglas A. Klumpp. "ChemInform Abstract: Friedel-Crafts Acylation with Amides." ChemInform 43, no. 44 (October 4, 2012): no. http://dx.doi.org/10.1002/chin.201244050.

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36

Kobayashi, Shū, Ichiro Komoto, and Jun-ichi Matsuo. "Catalytic Friedel-Crafts Acylation of Aniline Derivatives." Advanced Synthesis & Catalysis 343, no. 1 (January 29, 2001): 71–74. http://dx.doi.org/10.1002/1615-4169(20010129)343:1<71::aid-adsc71>3.0.co;2-j.

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37

Schmidt, Nina G., Tea Pavkov-Keller, Nina Richter, Birgit Wiltschi, Karl Gruber, and Wolfgang Kroutil. "Biocatalytic Friedel-Crafts Acylation and Fries Reaction." Angewandte Chemie 129, no. 26 (May 23, 2017): 7723–27. http://dx.doi.org/10.1002/ange.201703270.

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38

Chen, Mingfei, Ilia Guzei, Arnold L. Rheingold, and Harry W. Gibson. "Novel Macrocycle by Friedel−Crafts Acylation Cyclization." Macromolecules 30, no. 8 (April 1997): 2516–18. http://dx.doi.org/10.1021/ma960373d.

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39

Kawakami, Yoshiteru, and Yoshio Kabe. "Novelmeta-Selective Friedel–Crafts Acylation of Phenylsilsesquioxane." Chemistry Letters 39, no. 10 (October 5, 2010): 1082–83. http://dx.doi.org/10.1246/cl.2010.1082.

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40

Ogasawara, Masamichi, Morihiko Ogura, Takeshi Sakamoto, Susumu Watanabe, Sachie Arae, Kiyohiko Nakajima, and Tamotsu Takahashi. "Homoannular Double Friedel–Crafts Acylation of Phosphametallocenes." Organometallics 30, no. 18 (September 26, 2011): 5045–51. http://dx.doi.org/10.1021/om200678q.

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41

Kuznetsov, Yu V., L. G. Stolyarova, V. P. Lezina, M. M. Kazanskii, and L. D. Smirnov. "Friedel-Crafts acylation of 5-hydroxybenzimidazole derivatives." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 40, no. 8 (August 1991): 1715–17. http://dx.doi.org/10.1007/bf01172282.

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42

Li, Alexander Y. Z. "Intramolecular Friedel-Crafts Acylation Promoted by Hexafluoroisopropanol." Biophysical Journal 112, no. 3 (February 2017): 276a. http://dx.doi.org/10.1016/j.bpj.2016.11.1497.

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43

Tripp, Matthias W., and Ulrich Koert. "Synthesis of 6,13-difluoropentacene." Beilstein Journal of Organic Chemistry 16 (September 2, 2020): 2136–40. http://dx.doi.org/10.3762/bjoc.16.181.

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6,13-Difluoropentacene was synthesized from 1,4-difluorobenzene. Friedel–Crafts annulation of the latter with phthalic anhydride and subsequent reduction of the anthraquinone gave 1,4-difluoroanthracene. After ortho-lithiation and reaction with phthalic anhydride a carboxylic acid was obtained whose Friedel–Crafts acylation and subsequent reductive removal of the oxygen-functionalities resulted in the formation of the target compound. The HOMO–LUMO gap of 6,13-difluoropentacene was determined via UV–vis spectroscopy and compared to other fluorinated pentacenes.

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44

Deshmukh, Anjali P., Kamlesh J. Padiya, and Manikrao M. Salunkhe. "Friedel–Crafts Acylation Reaction using Polymer Supported Aluminium Chloride." Journal of Chemical Research 23, no. 9 (September 1999): 568–69. http://dx.doi.org/10.1177/174751989902300925.

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45

Chanda, Tanmoy, Sushobhan Chowdhury, Suvajit Koley, Namrata Anand, and Maya Shankar Singh. "Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel–Crafts acylation/Allan–Robinson reaction." Org. Biomol. Chem. 12, no. 45 (2014): 9216–22. http://dx.doi.org/10.1039/c4ob01743a.

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46

Matsumoto, Kazuya, Chisa Fukui, Riku Shoji, and Mitsutoshi Jikei. "Synthesis of aromatic polyketones by nonstoichiometric Friedel–Crafts polycondensation using AlCl3." Polymer Chemistry 11, no. 26 (2020): 4221–27. http://dx.doi.org/10.1039/d0py00534g.

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Aromatic polyketones were successfully synthesized by Friedel–Crafts acylation using AlCl₃ between aromatic dicarboxylic acid chlorides and 2,2′-dimethoxybiphenyl under both stoichiometric and nonstoichiometric conditions.

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47

Rajagopal, Shinaj K., Abbey M. Philip, Kalaivanan Nagarajan, and Mahesh Hariharan. "Progressive acylation of pyrene engineers solid state packing and colour via C–H⋯H–C, C–H⋯O and π–π interactions." Chem. Commun. 50, no. 63 (2014): 8644–47. http://dx.doi.org/10.1039/c4cc01897d.

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Sandwich herringbone–herringbone-brickwork-columnar crystal ordering, achieved through successive Friedel–Crafts acylation of pyrene, forms the basis for diverse solid-state colouring and blue–green–orange fluorescent crystals.

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48

Skorotetcky, M. S., O. V. Borshchev, M. S. Polinskaya, E. A. Zaborin, V. P. Chekusova, E. Yu Poimanova, D. S. Anisimov, et al. "Simple synthesis of alkyl derivatives of tetrathienoacene and their application in organic field-effect transistors." Journal of Materials Chemistry C 9, no. 32 (2021): 10216–21. http://dx.doi.org/10.1039/d1tc01469b.

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49

Abdolmaleki, Amir, Shadpour Mallakpour, and Sedigheh Borandeh. "Structure, morphology and electronic properties ofl-phenylalanine edge-functionalized graphite platelets through Friedel–Crafts acylation reaction." RSC Adv. 4, no. 104 (2014): 60052–57. http://dx.doi.org/10.1039/c4ra10387d.

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Edge functionalized graphite were prepared by Friedel–Crafts acylation withl-phenylalanine. The functionalized nanoplatelates are highly dispersible in polar solvents and shows enhanced electron transfer capability compared to pristine graphite.

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50

Tran, Phuong Hoang, Hai Truong Nguyen, and Thach Ngoc Le. "Benzoylation of aryl methyl ether using catalytic system of Gd(OTf)3/MSAA." Science and Technology Development Journal 18, no. 2 (June 30, 2015): 221–27. http://dx.doi.org/10.32508/stdj.v18i2.1187.

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The Friedel-Crafts acylation is an important reaction in organic synthesis. Benzoylation of aromatic compounds with benzoic acid as acylating reagent using catalytic system of Gd(OTf)3/MSAA was investigated under microwave irradiation. Catalytic system of Gd(OTf)3/MSAA was found to be an efficient catalyst for FriedelCrafts benzoylation under mild conditions. In addition, Gd(OTf)3/MSAA is safe-to-handle, simple clean work-up and gives good yield.

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