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Статті в журналах з теми "Dehydrogenative aromatization"

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Автор: Grafiati

Опубліковано: 10 грудня 2022

Оновлено: 28 січня 2023

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1

Liu, Xueli, Jun Chen, and Tianlin Ma. "Catalytic dehydrogenative aromatization of cyclohexanones and cyclohexenones." Organic & Biomolecular Chemistry 16, no. 45 (2018): 8662–76. http://dx.doi.org/10.1039/c8ob02351d.

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Анотація:

Prompted by the scant attention paid by published literature reviews to the comprehensive catalytic dehydrogenative aromatization of cyclohexa(e)nones, this review describes recent methods developed to-date involving transition-metal-catalyzed oxidative aromatization and metal-free strategies for the transformation of cyclohexa(e)nones to substituted phenols.

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2

Takayama, Satoshi, Takafumi Yatabe, Yu Koizumi, Xiongjie Jin, Kyoko Nozaki, Noritaka Mizuno, and Kazuya Yamaguchi. "Synthesis of unsymmetrically substituted triarylamines via acceptorless dehydrogenative aromatization using a Pd/C and p-toluenesulfonic acid hybrid relay catalyst." Chemical Science 11, no. 16 (2020): 4074–84. http://dx.doi.org/10.1039/c9sc06442g.

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3

Girard, Simon A., Huawen Huang, Feng Zhou, Guo-Jun Deng, and Chao-Jun Li. "Catalytic dehydrogenative aromatization: an alternative route to functionalized arenes." Organic Chemistry Frontiers 2, no. 3 (2015): 279–87. http://dx.doi.org/10.1039/c4qo00358f.

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4

Ding, Dong, Xiaobing Lv, Jian Li, Lin Qiu, Guangyang Xu, and Jiangtao Sun. "A Pd-catalyzed cascade reaction of N–H insertion and oxidative dehydrogenative aromatization: a new entry to 2-amino-phenols." Org. Biomol. Chem. 12, no. 24 (2014): 4084–88. http://dx.doi.org/10.1039/c4ob00652f.

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5

Liu, Xiao-Jun, Wen-Peng Wang, Cong-De Huo, Xi-Cun Wang, and Zheng-Jun Quan. "Palladium-catalyzed dehydrogenation of dihydro-heterocycles using isoprene as the hydrogen acceptor without oxidants." Catalysis Science & Technology 7, no. 3 (2017): 565–69. http://dx.doi.org/10.1039/c6cy02038k.

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6

Luo, Zheng, Yan Liu, Chao Wang, Danjun Fang, Junyu Zhou, and Huayou Hu. "Application of the Cu(i)/TEMPO/O2 catalytic system for aerobic oxidative dehydrogenative aromatization of pyrrolidines." Green Chemistry 21, no. 17 (2019): 4609–13. http://dx.doi.org/10.1039/c9gc01932d.

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Анотація:

A Cu(i)/TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy)-catalyzed aerobic oxidative dehydrogenative aromatization reaction of fully saturated pyrrolidines to synthesize multi-substituted pyrroles was developed for the first time.

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7

Wang, Qiang, Xincan Wang, Qiang Liu, Guanqun Xie, Shujiang Ding, Xiaoxia Wang, and Hongbo Fan. "Electrochemical one-pot synthesis of five-membered azaheterocycles via [4 + 1] cyclization." Organic Chemistry Frontiers 7, no. 23 (2020): 3912–17. http://dx.doi.org/10.1039/d0qo01068e.

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Анотація:

Five-membered N-heterocycles, such as oxadiazoles, thiadiazoles, oxazolines and imidazoles, have been prepared via electrochemical oxidation/[4 + 1] cyclization/dehydrogenative aromatization in one pot from readily available materials.

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8

Deng, Kun, Huawen Huang, and Guo-Jun Deng. "Recent advances in the transition metal-free oxidative dehydrogenative aromatization of cyclohexanones." Organic & Biomolecular Chemistry 19, no. 29 (2021): 6380–91. http://dx.doi.org/10.1039/d1ob00908g.

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Анотація:

This review focuses on the transition metal-free oxidative dehydrogenative aromatization reactions of cyclohexanones, with an emphasis on the scope and limitations, as well as the mechanisms of these reactions.

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9

Luo, Zheng, Yan Liu, Chao Wang, Danjun Fang, Junyu Zhou, and Huayou Hu. "Correction: Application of the Cu(i)/TEMPO/O2 catalytic system for aerobic oxidative dehydrogenative aromatization of pyrrolidines." Green Chemistry 22, no. 1 (2020): 270. http://dx.doi.org/10.1039/c9gc90114k.

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Анотація:

Correction for ‘Application of the Cu(i)/TEMPO/O₂ catalytic system for aerobic oxidative dehydrogenative aromatization of pyrrolidines’ by Zheng Luo et al., Green Chem., 2019, 21, 4609–4613.

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10

Jin, Xiongjie, Kento Taniguchi, Kazuya Yamaguchi, Kyoko Nozaki, and Noritaka Mizuno. "A Ni–Mg–Al layered triple hydroxide-supported Pd catalyst for heterogeneous acceptorless dehydrogenative aromatization." Chemical Communications 53, no. 38 (2017): 5267–70. http://dx.doi.org/10.1039/c7cc01182b.

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In the presence of a Ni–Mg–Al layered triple hydroxide-supported Pd catalyst, the acceptorless dehydrogenative aromatization of a wide range of substrates efficiently proceeded with the liberation of molecular hydrogen.

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11

Guo, Tenglong, Quanbin Jiang, and Zhengkun Yu. "Palladium-catalyzed oxidative annulation of in situ generated enones to pyrroles: a concise route to functionalized indoles." Organic Chemistry Frontiers 2, no. 10 (2015): 1361–65. http://dx.doi.org/10.1039/c5qo00203f.

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Анотація:

Pd(ii)-catalyzed, Cu(ii)-mediated indole synthesis from pyrroles and 3-chloropropiophenones has been efficiently achieved. In-situ generated enones were employed for the establishment of a benzene ring onto a pyrrole backbone via dehydrochlorination/C–H olefination/cycloaddition/dehydrogenative aromatization.

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12

Srilatha, Marepally, Vallabhareddy Satteyyanaidu, Chepyala Krishna Reddy, and Venkata Subba Reddy Basireddy. "A Unified Total Synthesis of Isocyclocapitelline and Cyclocapitelline." Natural Product Communications 15, no. 11 (November 1, 2020): 1934578X2096787. http://dx.doi.org/10.1177/1934578x20967871.

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A facile and concise synthesis of β-carboline alkaloids, such as (–)-isocyclocapitelline and (+)-cyclocapitelline, has been achieved from commercially available geraniol through a unified strategy. The key steps involved in this synthesis are Sharpless epoxidation, intramolecular ring opening of epoxide, Pictet-Spengler reaction, and dehydrogenative aromatization using 10% palladium/carbon in xylene under neutral conditions.

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13

Oyama, Takashi, Takafumi Yatabe, Xiongjie Jin, Noritaka Mizuno, and Kazuya Yamaguchi. "Heterogeneously Palladium-catalyzed Acceptorless Dehydrogenative Aromatization of Cyclic Amines." Chemistry Letters 48, no. 6 (June 5, 2019): 517–20. http://dx.doi.org/10.1246/cl.190080.

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14

Wang, Zhen, Cheng Li, Huawen Huang, and Guo-Jun Deng. "Elemental Sulfur-Promoted Aerobic Dehydrogenative Aromatization of Cyclohexanones with Amines." Journal of Organic Chemistry 85, no. 14 (June 24, 2020): 9415–23. http://dx.doi.org/10.1021/acs.joc.0c01122.

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15

Hajra, Alakananda, Ye Wei, and Naohiko Yoshikai. "Palladium-Catalyzed Aerobic Dehydrogenative Aromatization of Cyclohexanone Imines to Arylamines." Organic Letters 14, no. 21 (October 16, 2012): 5488–91. http://dx.doi.org/10.1021/ol302568b.

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16

Lin, Long, Xiaotong Zhang, Ning He, Jiaxu Liu, Qin Xin, and Hongchen Guo. "Operando Dual Beam FTIR Study of Hydroxyl Groups and Zn Species over Defective HZSM-5 Zeolite Supported Zinc Catalysts." Catalysts 9, no. 1 (January 17, 2019): 100. http://dx.doi.org/10.3390/catal9010100.

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Анотація:

A series of defective ZSM-5 zeolites (~300 nm, SiO2/Al2O3 ratio of 55, 100, 480 and 950) were systematically studied by XRD, SEM, 29Si MAS NMR, argon physisorption, NH3-TPD and FT-IR technologies. The nature, the amount and the accessibility of the acid sites of defective ZSM-5 zeolites are greatly different from reported ZSM-5 zeolites with a perfect crystal structure. The Brønsted acid sites (Si(OH)Al) with strong acid strength and the Brønsted acid sites (hydroxyl nests) with weak acid strength co-existed over defective ZSM-5 zeolites, which leads to a unique catalytic function. Zn(C2H5)2 was grafted onto defective ZSM-5 zeolites through the chemical liquid deposition (CLD) method. Interestingly, FT-IR spectroscopic studies found that Zn(C2H5)2 was preferentially grafted on the hydroxyl nests with weak acid strength rather than the Si(OH)Al groups with strong acid strength over different defective ZSM-5 zeolites. In particular, home-built operando dual beam FTIR-MS was applied to study the catalytic performance of Zn species located in different sites of defective ZSM-5 zeolites under real n-hexane transformation conditions. Results show that Zn species grafted over hydroxyl nests obtain better dehydrogenative aromatization performance than Zn species over Si(OH)Al groups. This study provides guidance for the rational design of highly efficient alkane dehydrogenative aromatization catalysts.

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17

Tao, Shao-Kun, Shan-Yong Chen, Mei-Lin Feng, Jia-Qi Xu, Mao-Lin Yuan, Hai-Yan Fu, Rui-Xiang Li, Hua Chen, Xue-Li Zheng, and Xiao-Qi Yu. "Electrochemical Cross-Dehydrogenative Aromatization Protocol for the Synthesis of Aromatic Amines." Organic Letters 24, no. 4 (January 21, 2022): 1011–16. http://dx.doi.org/10.1021/acs.orglett.1c04129.

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18

Muralirajan, Krishnamoorthy, Rajesh Kancherla, and Magnus Rueping. "Dehydrogenative Aromatization and Sulfonylation of Pyrrolidines: Orthogonal Reactivity in Photoredox Catalysis." Angewandte Chemie 130, no. 45 (October 11, 2018): 15003–7. http://dx.doi.org/10.1002/ange.201808427.

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19

Girard, Simon A., Huawen Huang, Feng Zhou, Guo-Jun Deng, and Chao-Jun Li. "ChemInform Abstract: Catalytic Dehydrogenative Aromatization: An Alternative Route to Functionalized Arenes." ChemInform 46, no. 25 (June 2015): no. http://dx.doi.org/10.1002/chin.201525275.

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20

Muralirajan, Krishnamoorthy, Rajesh Kancherla, and Magnus Rueping. "Dehydrogenative Aromatization and Sulfonylation of Pyrrolidines: Orthogonal Reactivity in Photoredox Catalysis." Angewandte Chemie International Edition 57, no. 45 (October 11, 2018): 14787–91. http://dx.doi.org/10.1002/anie.201808427.

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21

Sako, Makoto, Romain Losa, Tomohiro Takiishi, Giang Vo-Thanh, Shinobu Takizawa, and Hiroaki Sasai. "Vanadium(V) Complex-Catalyzed One-Pot Synthesis of Phenanthridines via a Pictet-Spengler-Dehydrogenative Aromatization Sequence." Catalysts 10, no. 8 (August 2, 2020): 860. http://dx.doi.org/10.3390/catal10080860.

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Анотація:

Phenanthridine and its derivatives are important structural motifs that exist in natural products, biologically active compounds, and functional materials. Here, we report a mild, one-pot synthesis of 6-arylphenanthridine derivatives by a sequential cascade Pictet-Spengler-dehydrogenative aromatization reaction mediated by oxovanadium(V) complexes under aerobic conditions. The reaction of 2-(3,5-dimethoxyphenyl)aniline with a range of commercially available aryl aldehydes provided the desired phenanthridine derivatives in up to 96% yield. The ability of vanadium(V) complexes to function as efficient redox and Lewis acid catalysts enables the sequential reaction to occur under mild conditions.

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22

Jin, Xiongjie, Kyoko Nozaki, Noritaka Mizuno, and Kazuya Yamaguchi. "Dehydrogenative Aromatization Reactions by Supported Pd or Au-Pd Alloy Nanoparticles Catalysts." Journal of Synthetic Organic Chemistry, Japan 77, no. 6 (June 1, 2019): 566–75. http://dx.doi.org/10.5059/yukigoseikyokaishi.77.566.

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23

Koike, Kenta, and Satoshi Ueno. "Palladium-catalyzed Dehydrogenative [3+3] Aromatization of Propyl Ketones and Allyl Carbonates." Chemistry Letters 51, no. 4 (April 5, 2022): 489–92. http://dx.doi.org/10.1246/cl.220032.

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24

Zeng, Yuyao, Bowei Wang, Yang Li, Xilong Yan, Ligong Chen, and Yue Wang. "Ba-Doped Pd/Al2O3 for Continuous Synthesis of Diphenylamine via Dehydrogenative Aromatization." Industrial & Engineering Chemistry Research 59, no. 4 (January 3, 2020): 1436–45. http://dx.doi.org/10.1021/acs.iecr.9b04567.

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25

Schendera, Eva, Lisa‐Natascha Unkel, Phung Phan Huyen Quyen, Gwen Salkewitz, Frank Hoffmann, Alexander Villinger, and Malte Brasholz. "Visible‐Light‐Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines." Chemistry – A European Journal 26, no. 1 (November 27, 2019): 269–74. http://dx.doi.org/10.1002/chem.201903921.

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26

Zhang, Xuan, Liang Xu, Xitao Wang, Ning Ma, and Feifei Sun. "Dehydrogenative Aromatization of Saturated Aromatic Compounds by Graphite Oxide and Molecular Sieves." Chinese Journal of Chemistry 30, no. 7 (June 2012): 1525–30. http://dx.doi.org/10.1002/cjoc.201200174.

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27

Hajra, Alakananda, Ye Wei, and Naohiko Yoshikai. "ChemInform Abstract: Palladium-Catalyzed Aerobic Dehydrogenative Aromatization of Cyclohexanone Imines to Arylamines." ChemInform 44, no. 11 (March 8, 2013): no. http://dx.doi.org/10.1002/chin.201311056.

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28

Lin, Wei, Ye Song, Lei Han, Xue Yang, Jun Liu, and Bo Peng. "Dehydrogenative aromatization of 1-octene over multifunctional Ni/ZSM-5-P-Fe catalyst." Fuel 299 (September 2021): 120890. http://dx.doi.org/10.1016/j.fuel.2021.120890.

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29

Hirao, Toshikazu, Makoto Mori та Yoshiki Ohshiro. "Versatile Dehydrogenative Aromatization of α,β-Unsaturated Cyclohexenones with VO(OEt)Cl2-Me3SiOTf". Chemistry Letters 20, № 5 (травень 1991): 783–84. http://dx.doi.org/10.1246/cl.1991.783.

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30

Zhang, Xuan, Liang Xu, Xitao Wang, Ning Ma, and Feifei Sun. "ChemInform Abstract: Dehydrogenative Aromatization of Saturated Aromatic Compounds by Graphite Oxide and Molecular Sieves." ChemInform 43, no. 49 (November 19, 2012): no. http://dx.doi.org/10.1002/chin.201249034.

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31

Jiang, Pingyu, Shanping Chen, Huawen Huang, Kai Hu, Yi Xia, and Guo-Jun Deng. "Metal-free synthesis of indolo[2,3-b]indoles through aerobic cascade dehydrogenative aromatization/oxidative annulation." Green Synthesis and Catalysis 2, no. 1 (February 2021): 78–81. http://dx.doi.org/10.1016/j.gresc.2021.01.004.

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32

Kim, Jinhee, Youngtaek Moon, Suhyun Lee, and Sungwoo Hong. "A Pd-Catalyzed one-pot dehydrogenative aromatization and ortho-functionalization sequence of N-acetyl enamides." Chemical Communications 50, no. 24 (2014): 3227. http://dx.doi.org/10.1039/c4cc00027g.

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33

Wang, Zhen, Xiangui Chen, Hao Xie, Dahan Wang, Huawen Huang, and Guo-Jun Deng. "Synthesis of o-Arylenediamines through Elemental Sulfur-Promoted Aerobic Dehydrogenative Aromatization of Cyclohexanones with Arylamines." Organic Letters 20, no. 17 (August 21, 2018): 5470–73. http://dx.doi.org/10.1021/acs.orglett.8b02387.

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34

Junaid, Ahmad, Felicia Phei Lin Lim, Edward R. T. Tiekink, and Anton V. Dolzhenko. "New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization." ACS Combinatorial Science 21, no. 7 (June 10, 2019): 548–55. http://dx.doi.org/10.1021/acscombsci.9b00079.

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35

Liu, Yan, Huayou Hu, Xiang Wang, Sanjun Zhi, Yuhe Kan, and Chao Wang. "Synthesis of Pyrrole via a Silver-Catalyzed 1,3-Dipolar Cycloaddition/Oxidative Dehydrogenative Aromatization Tandem Reaction." Journal of Organic Chemistry 82, no. 8 (April 5, 2017): 4194–202. http://dx.doi.org/10.1021/acs.joc.7b00180.

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36

HIRAO, T., M. MORI та Y. OHSHIRO. "ChemInform Abstract: Versatile Dehydrogenative Aromatization of α,β-Unsaturated Cyclohexenones with VO(OEt)Cl2-Me3SiOTf." ChemInform 23, № 9 (22 серпня 2010): no. http://dx.doi.org/10.1002/chin.199209153.

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37

Xu, Juanfang, Huayou Hu, Yun Liu, Xiang Wang, Yuhe Kan, and Chao Wang. "Four-Component Reaction for the Synthesis of Indolizines by Copper-Catalyzed Aerobic Oxidative Dehydrogenative Aromatization." European Journal of Organic Chemistry 2017, no. 2 (December 5, 2016): 257–61. http://dx.doi.org/10.1002/ejoc.201601272.

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38

Utecht-Jarzyńska, Greta, Anna Kowalczyk, and Marcin Jasiński. "Fluorinated and Non-Fluorinated 1,4-Diarylpyrazoles via MnO2-Mediated Mechanochemical Deacylative Oxidation of 5-Acylpyrazolines." Molecules 27, no. 23 (December 2, 2022): 8446. http://dx.doi.org/10.3390/molecules27238446.

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Анотація:

A solvent-free two-step synthesis of polyfunctionalized pyrazoles under ball-milling mechanochemical conditions was developed. The protocol comprises (3 + 2)-cycloaddition of in situ generated nitrile imines and chalcones, followed by oxidation of the initially formed 5-acylpyrazolines with activated MnO2. The second step proceeds via an exclusive deacylative pathway, to give a series of 1,4-diarylpyrazoles functionalized with a fluorinated (CF3) or non-fluorinated (Ph, COOEt, Ac) substituent at C(3) of the heterocyclic ring. In contrast, MnO2-mediated oxidation of a model isomeric 4-acylpyrazoline proceeded with low chemoselectivity, leading to fully substituted pyrazole as a major product formed via dehydrogenative aromatization. The presented approach extends the scope of the known methods carried out in organic solvents and enables the preparation of polyfunctionalized pyrazoles, which are of general interest in medicine and material sciences.

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39

Taniguchi, Kento, Xiongjie Jin, Kazuya Yamaguchi, and Noritaka Mizuno. "Facile access to N-substituted anilines via dehydrogenative aromatization catalysis over supported gold–palladium bimetallic nanoparticles." Catalysis Science & Technology 6, no. 11 (2016): 3929–37. http://dx.doi.org/10.1039/c5cy01908g.

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Анотація:

In the presence of a gold–palladium alloy nanoparticle catalyst (Au–Pd/Al₂O₃) and styrene, various kinds of structurally diverse N-substituted anilines (twenty three examples) could be synthesized starting from cyclohexanones and amines.

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40

Jiang, Wei, Yajun Wang, Pengfei Niu, Zhengjun Quan, Yingpeng Su, and Congde Huo. "Double-Oxidative Dehydrogenative (DOD) [4 + 2]-Cyclization/Oxidative Aromatization Tandem Reaction of Glycine Derivatives with Ethylbenzenes." Organic Letters 20, no. 15 (July 23, 2018): 4649–53. http://dx.doi.org/10.1021/acs.orglett.8b01941.

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41

Zhou, Wei, Jiaxu Liu, Long Lin, Xiaotong Zhang, Ning He, Chunyan Liu, and Hongchen Guo. "Enhanced Dehydrogenative Aromatization of Propane by Incorporating Fe and Pt into the Zn/HZSM-5 Catalyst." Industrial & Engineering Chemistry Research 57, no. 48 (October 29, 2018): 16246–56. http://dx.doi.org/10.1021/acs.iecr.8b03865.

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42

Zhao, Ziquan, Yan Sun, Lilin Wang, Xuan Chen, Yanpei Sun, Long Lin, Yulin Tang, Fei Li та Dongyin Chen. "Organic base-promoted efficient dehydrogenative/decarboxylative aromatization of tetrahydro-β-carbolines into β-carbolines under air". Tetrahedron Letters 60, № 11 (березень 2019): 800–804. http://dx.doi.org/10.1016/j.tetlet.2019.02.020.

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43

Taniguchi, Kento, Xiongjie Jin, Kazuya Yamaguchi, Kyoko Nozaki, and Noritaka Mizuno. "Versatile routes for synthesis of diarylamines through acceptorless dehydrogenative aromatization catalysis over supported gold–palladium bimetallic nanoparticles." Chemical Science 8, no. 3 (2017): 2131–42. http://dx.doi.org/10.1039/c6sc04455g.

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Анотація:

In the presence of Au–Pd/TiO₂, various kinds of symmetrically and unsymmetrically substituted diarylamines could effectively be synthesized starting from various combinations of substrates.

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44

Wen, Lixian, Lin Tang, Yu Yang, Zhenggen Zha, and Zhiyong Wang. "Ligand-Free Pd-Catalyzed Domino Synthesis of Carbazoles via Dehydrogenative Aromatization/C(sp2)–C(sp2) Coupling Sequence." Organic Letters 18, no. 6 (February 26, 2016): 1278–81. http://dx.doi.org/10.1021/acs.orglett.6b00193.

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45

Kim, Jinhee, Youngtaek Moon, Suhyun Lee, and Sungwoo Hong. "ChemInform Abstract: A Pd-Catalyzed One-Pot Dehydrogenative Aromatization and ortho-Functionalization Sequence of N-Acetyl Enamides." ChemInform 45, no. 33 (July 28, 2014): no. http://dx.doi.org/10.1002/chin.201433089.

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46

Mohamad Arshad, Ahmad Saifuddin, Ramu Meesala, Nur Aziah Hanapi та Mohd Nizam Mordi. "A convenient synthesis of β-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-β-carbolines under air". Tetrahedron 83 (березень 2021): 131960. http://dx.doi.org/10.1016/j.tet.2021.131960.

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