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Journal articles on the topic 'Friedel-Crafts'

Author: Grafiati

Published: 4 June 2021

Last updated: 18 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

Kolb, Kenneth E., and Kurt W. Field. "Friedel-Crafts alkylation products." Journal of Chemical Education 68, no. 1 (January 1991): 86. http://dx.doi.org/10.1021/ed068p86.3.

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3

Schmidt, Nina Gabriele, Tea Pavkov-Keller, Nina Richter, Karl Gruber, Birgit Wiltschi, and Wolfgang Kroutil. "Biocatalytic Friedel–Crafts acylations." New Biotechnology 33 (July 2016): S2. http://dx.doi.org/10.1016/j.nbt.2016.06.733.

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4

Yamaguchi, Masahiko, Yoshiyuki Kido, Akio Hayashi, and Masahiro Hirama. "Friedel-Crafts-β-Silylvinylierungen." Angewandte Chemie 109, no. 12 (June 16, 1997): 1370–72. http://dx.doi.org/10.1002/ange.19971091219.

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5

Völler, Jan-Stefan. "Biocatalytic Friedel–Crafts alkylation." Nature Catalysis 2, no. 3 (March 2019): 180. http://dx.doi.org/10.1038/s41929-019-0262-2.

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6

Plesch, P. H. "Symposium on Friedel–Crafts catalysts and polymerization." Notes and Records of the Royal Society of London 53, no. 1 (January 22, 1999): 135–41. http://dx.doi.org/10.1098/rsnr.1999.0068.

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On 15 September 1945, Michael Polanyi, F.R.S., Professor of Physical Chemistry at the University of Manchester, convened there a one–day meeting entitled ‘Symposium on Friedel–Crafts Catalysts and Polymerization’. The morning was devoted to Friedel-Crafts catalysts and the afternoon to polymerization.

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7

Patel, Pradip S., and Shanti R. Patel. "Friedel-Crafts Polymers. 9. Friedel-Crafts Polycondensation of 4,4′-Dichloroacetyldiphenyl Ether with Phenols." Journal of Macromolecular Science: Part A - Chemistry 24, no. 1 (January 1987): 67–74. http://dx.doi.org/10.1080/00222338708058509.

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8

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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9

El-Zohry, Maher F. "Nonconventional Friedel-Crafts Chemistry. VII. On Homoannular and Heteroannular Reactions of Ferrocene with Bifunctional Moieties under Friedel-Crafts Conditions." Collection of Czechoslovak Chemical Communications 58, no. 5 (1993): 1203–7. http://dx.doi.org/10.1135/cccc19931203.

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The utilization of ferrocene in the organic synthesis and its uses in Friedel-Crafts chemistry, together with our interest in this area, prompted us to investigate the reaction of ferrocene with halo acid chlorides and α,β-unsaturated acid chlorides under different Friedel-Crafts conditions with the aim to employ these reactions in the syntheses of polycyclic ferrocene derivatives.

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10

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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11

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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12

Jiang, Zhen-Yu, Ji-Rong Wu, Li Li, Xi-Huai Chen, Guo-Qiao Lai, Jian-Xiong Jiang, Yixin Lu, and Li-Wen Xu. "Efficient Lewis acid-assisted Brønsted acid (LBA) catalysis in the iron-catalyzed Friedel-Crafts alkylation reaction of indoles." Open Chemistry 8, no. 3 (June 1, 2010): 669–73. http://dx.doi.org/10.2478/s11532-010-0016-0.

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AbstractLewis acid-assisted Brønsted acid (LBA) catalysis was proposed for the iron-catalyzed Friedel-Crafts alkylation of indoles with chalcones. This proposal was supported by the ESI-MS and cyclic voltammetry. The addition of acac to the iron-catalyzed Friedel-Crafts alkylation of indoles with chalcones created a powerful catalytic system, which makes the alkylation reactions occur easily under mild conditions.

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13

Roy, Snigdha. "Prins-Friedel-Crafts Cyclization: Synthesis of Diversely Functionalized Six- Membered Oxacycles." Current Organic Chemistry 25, no. 5 (March 15, 2021): 635–51. http://dx.doi.org/10.2174/1385272825666210114105020.

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Prins cyclization is a well-established synthetic protocol to generate a wide range of important oxygen heterocycles. It is a cyclization reaction performed by an oxocarbenium ion that undergoes an intramolecular pi-bond attack to construct a new carbon-carbon bond. When this cyclization process is conjugated with Friedel-Crafts reaction, it further expands the synthetic potential by fabricating two different carbon-carbon bonds in one single reaction. Different acid catalysts mediated the coupled Prins-Friedel-Crafts reaction which is conducted both in stepwise as well as in tandem fashion. In the stepwise route, three different reacting components were utilized whereas, the tandem methodology required proper modification of the initial substrate molecule. An array of allylic, propargylic, other related alkenols, and carbonyl reactants were employed to carry out the cyclization process. Several oxygenated heterocycles equipped with diverse functionalities were constructed in a stereoselective manner which again reinforced the significance of this cyclization protocol undoubtedly. The present mini-review highlights the utilization of different one-pot stepwise Prins-Friedel-Crafts reactions and the subsequent development of cascade Prins- Friedel-Crafts cyclization process to furnish intricate molecular architectures of vital six-membered oxacycles.

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14

Lu, Hai-Hua, Fen Tan, and Wen-Jing Xiao. "Enantioselective Organocatalytic Friedel-Crafts Alkylations." Current Organic Chemistry 15, no. 24 (December 1, 2011): 4022–45. http://dx.doi.org/10.2174/138527211798109196.

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15

Tanaka, Shinji. "Catalytic Asymmetric Friedel-Crafts Reaction." Journal of Synthetic Organic Chemistry, Japan 66, no. 3 (2008): 249–50. http://dx.doi.org/10.5059/yukigoseikyokaishi.66.249.

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16

Mindl, Jaromír, and Giovanni Vittorio Sebastiani. "Friedel-Crafts chloroethylation of hexamethylbenzene." Collection of Czechoslovak Chemical Communications 52, no. 12 (1987): 2936–45. http://dx.doi.org/10.1135/cccc19872936.

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The reaction of hexamethylbenzene I with 1,2-dichloroethane in the presence of aluminium chloride gives 1-(2-chloroethyl)-1,2,3,4,5,6-hexamethylbenzenium salt (II) which is decomposed with water. The decomposition products include hexamethylbenzene (I), 3-(2-chloroethyl)-1,2,3,4,5-pentamethyl-6-methylene-1,4-cyclohexadiene (IIIa), 5-(2-chloroethyl)-1,2,3,4,5-pentamethyl-6-methylene-1,3-cyclohexadiene (IIIb), and 1-(2-chloroethyl)-2,3,4,5,6-pentamethylbenzene (IV). The compounds IIIa and IIIb are rearranged into 1-(3-chloropropyl)-2,3,4,5,6-pentamethylbenzene (V).

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17

Terrasson, Vincent, Renata Marcia de Figueiredo, and Jean Marc Campagne. "Organocatalyzed Asymmetric Friedel-Crafts Reactions." European Journal of Organic Chemistry 2010, no. 14 (March 4, 2010): 2635–55. http://dx.doi.org/10.1002/ejoc.200901492.

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18

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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19

Meima, G. R., G. S. Lee, and J. M. Garces. "ChemInform Abstract: Friedel-Crafts Alkylation." ChemInform 33, no. 41 (May 19, 2010): no. http://dx.doi.org/10.1002/chin.200241267.

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20

Prajapati, Sushma, Abhinav Prasoon Mishra, and Ashish Srivastava. "ChemInform Abstract: Friedel-Crafts Reaction." ChemInform 43, no. 28 (June 14, 2012): no. http://dx.doi.org/10.1002/chin.201228266.

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21

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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22

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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23

Olah, George A., Imre Bucsi, Dong Soo Ha, Robert Aniszfeld, Chang Soo Lee, and G. K. Surya Prakash. "Friedel-Crafts Reactions of Buckminsterfullerene." Fullerene Science and Technology 5, no. 2 (March 1997): 389–405. http://dx.doi.org/10.1080/15363839708011999.

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24

Nakano, Hirofumi, and Tomoya Kitazume. "Friedel-Crafts reactionin fluorous fluids." Green Chemistry 1, no. 4 (1999): 179–81. http://dx.doi.org/10.1039/a903544c.

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25

Patel, J. L., P. T. Amin, and S. R. Patel. "Note Friedel-Crafts Polymers. 11. Friedel-Crafts Polymers from 4,4′-Dichloromethyldiphenyl Ether and Chlorophenols." Journal of Macromolecular Science: Part A - Chemistry 26, no. 4 (April 1989): 727–30. http://dx.doi.org/10.1080/00222338908052005.

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26

Yıldız, Tülay, İrem Baştaş, and Hatice Başpınar Küçük. "Transition-metal-free intramolecular Friedel–Crafts reaction by alkene activation: A method for the synthesis of some novel xanthene derivatives." Beilstein Journal of Organic Chemistry 17 (August 30, 2021): 2203–8. http://dx.doi.org/10.3762/bjoc.17.142.

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In this work, new derivatives (substituted 9-methyl-9-arylxanthenes) of xanthene compounds (5a–l) of possible biological significance were synthesized by developing a new synthesis method. In order to obtain xanthene derivatives, the original alkene compounds to be used as the starting materials were synthesized in four steps using appropriate reactions. A cyclization reaction by intramolecular Friedel–Crafts alkylation was carried out in order to synthesize the desired xanthene derivatives using the alkenes as starting compounds. The intramolecular Friedel–Crafts reaction was catalyzed by trifluoroacetic acid (TFA) and provided some novel substituted 9-methyl-9-arylxanthenes with good yields at room temperature within 6–24 hours. As a result, an alkene compound was used for activation with TFA in the synthesis of xanthene through intramolecular Friedel–Crafts alkylation for the first time.

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27

Buchcic, Aleksandra, Anna Zawisza, Stanisław Leśniak, and Michał Rachwalski. "Asymmetric Friedel–Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines." Catalysts 10, no. 9 (August 26, 2020): 971. http://dx.doi.org/10.3390/catal10090971.

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Over the course of the present studies, a series of optically pure phosphines functionalized by chiral aziridines was synthesized in reasonable/good chemical yields. Their catalytic activity was checked in the enantioselective Friedel–Crafts alkylation of indoles by β-nitrostyrene in the presence of a copper(I) trifluoromethanesulfonate benzene complex. The corresponding Friedel–Crafts products were achieved efficiently in terms of chemical yield and enantioselectivity (up to 85% in some cases).

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28

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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29

Zheng, Jie, Shuyu Meng, and Quanrui Wang. "Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols." Beilstein Journal of Organic Chemistry 17 (June 22, 2021): 1481–89. http://dx.doi.org/10.3762/bjoc.17.104.

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The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF3·Et2O results in an intramolecular Prins reaction affording intermediary benzyl carbenium ions, which are then trapped by a variety of electron-rich aromatics via Friedel–Crafts alkylation. This cascade Prins/Friedel–Crafts cyclization protocol paves an expedient path to medicinally useful 4-aryltetralin-2-ol and 5-aryltetrahydro-5H-benzo[7]annulen-7-ol derivatives.

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30

Slootmaekers, P. J., R. Roosen, and J. Verhulst. "The Friedel-Crafts Acylation Reaction I. Substituent Effect in the Friedel-Crafts Benzoylation of Toluene." Bulletin des Sociétés Chimiques Belges 71, no. 7-8 (September 1, 2010): 446–65. http://dx.doi.org/10.1002/bscb.19620710708.

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31

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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32

Nguyen, Hai Truong, and Phuong Hoang Tran. "Friedel-Crafts acetylation of indole, 5-methoxyindole and 5-chloroindole using copper triflate under microwave irradiation." Science and Technology Development Journal 19, no. 4 (December 31, 2016): 177–84. http://dx.doi.org/10.32508/stdj.v19i4.621.

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Friedel-Crafts acetylation is an important reaction in organic synthesis processes. Acetylation of indole derivatives with acetic anhydride as acylating reagent using Cu(OTf)2 as a catalyst has been investigated under microwave irradiation. Different from traditional Lewis acidic catalyst, Cu(OTf)2 was found to be an efficient catalyst for Friedel-Crafts acetylation of indoles under mild conditions. Moreover, Cu(OTf)2 was safe-to-handle, recovered and reused several times without significant loss of catalytic activity.

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33

Li, Cong Qi, Bo Yu, Cheng Wang, Yong Xi Li, and Yu Chen. "An Easy Route for the Preparation of Soluble High Molecular Weight Polymer Under Friedel-Crafts Conditions." Advanced Materials Research 887-888 (February 2014): 989–92. http://dx.doi.org/10.4028/www.scientific.net/amr.887-888.989.

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A facile synthetic method that would be applied to polycondensation reaction between monomer A with bifunctional hydroxyl groups and monomer B with bifunctional reactive hydrogen atoms under Friedel-Crafts conditions was described. This approach, which has the advantage of short reaction time, high yield and simple synthesis operation, opens a way to prepare soluble high molecular weight polymers by the polycondensation reaction between monomer A with bifunctional hydroxyl groups and monomer B with bifunctional reactive hydrogen atoms under Friedel-Crafts conditions.

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34

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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35

El-Aal, Abd, and Ali Khalaf. "Modern Friedel-Crafts chemistry: Part 36. Facile synthesis of some new pyrido[3,2,1-jk]carbazoles via Friedel-Crafts cyclialkylations." Journal of the Serbian Chemical Society 78, no. 5 (2013): 611–19. http://dx.doi.org/10.2298/jsc120520098a.

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An efficient methodology for the synthesis of novel substituted pyrido[3,2,1-jk]carbazole via Friedel-Crafts cyclialkylations is reported. The methodology was realized by three-step protocol involved the addition of carbazole to 3-methylcrotononitrile. The resulted nitrile was hydrolyzed to desired ester, followed by addition of Grignard reagents to afford tertiary alcohols and/or reacted directly with different Grignard reagent to form the desired ketones. The later ketones were converted to both secondary and tertiary alcohols by reduction with LAH and addition of Grignard reagents respectively. These carbinols were cyclialkylated under Friedel-Crafts conditions catalyzed by AlCl3/CH3NO2, PTSA and PPA to give tri-and tetrasubstituted pyrido[3,2,1-jk]carbazole.

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36

Heravi, Majid M., Vahideh Zadsirjan, Baharak Masoumi, and Masumeh Heydari. "Organometal-catalyzed asymmetric Friedel-Crafts reactions." Journal of Organometallic Chemistry 879 (January 2019): 78–138. http://dx.doi.org/10.1016/j.jorganchem.2018.10.011.

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37

Grundl, Marc A., Anne Kaster, Ellen D. Beaulieu, and Dirk Trauner. "Development of a Friedel−Crafts Triflation." Organic Letters 8, no. 24 (November 2006): 5429–32. http://dx.doi.org/10.1021/ol061980g.

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38

Tsoung, Jennifer, Katja Krämer, Adam Zajdlik, Clemence Liébert, and Mark Lautens. "Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes." Journal of Organic Chemistry 76, no. 21 (November 4, 2011): 9031–45. http://dx.doi.org/10.1021/jo201781x.

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39

RITTER, STEVE. "FRIEDEL-CRAFTS TAKES A NEW GIG." Chemical & Engineering News Archive 89, no. 18 (May 2, 2011): 9. http://dx.doi.org/10.1021/cen-v089n018.p009.

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40

Sibi, M., J. Coulomb, and L. Stanley. "Enantioselective Protonation of Friedel-Crafts Intermediates." Synfacts 2009, no. 03 (February 19, 2009): 0302. http://dx.doi.org/10.1055/s-0028-1087773.

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41

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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42

Macquarrie, Duncan J. "ChemInform Abstract: Industrial Friedel-Crafts Chemistry." ChemInform 41, no. 48 (November 4, 2010): no. http://dx.doi.org/10.1002/chin.201048267.

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43

YAMAGUCHI, M., Y. KIDO, A. HAYASHI, and M. HIRAMA. "ChemInform Abstract: Friedel-Crafts β-Silylvinylations." ChemInform 28, no. 39 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199739069.

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44

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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45

Böeseken, J. "La réaction de Friedel et Crafts." Recueil des Travaux Chimiques des Pays-Bas et de la Belgique 30, no. 4 (September 3, 2010): 148–50. http://dx.doi.org/10.1002/recl.19110300403.

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46

Hayashi, Ryuji, and Gregory R. Cook. "ChemInform Abstract: Friedel-Crafts-type Cyclizations." ChemInform 41, no. 38 (August 26, 2010): no. http://dx.doi.org/10.1002/chin.201038237.

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47

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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48

Szuromi, P. D. "CHEMISTRY: Giving Friedel-Crafts a Hand." Science 292, no. 5517 (April 27, 2001): 603d—603. http://dx.doi.org/10.1126/science.292.5517.603d.

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49

de Nanteuil, Florian, Joachim Loup, and Jérôme Waser. "Catalytic Friedel–Crafts Reaction of Aminocyclopropanes." Organic Letters 15, no. 14 (July 2013): 3738–41. http://dx.doi.org/10.1021/ol401616a.

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50

Göndös, Gy, and I. Kapocsi. "Friedel-Crafts reaction with FeCl3-graphite." Journal of Physics and Chemistry of Solids 57, no. 6-8 (June 1996): 855–57. http://dx.doi.org/10.1016/0022-3697(95)00362-2.

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