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Статті в журналах з теми "Copper catalyzed synthesis"

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Автор: Grafiati

Опубліковано: 6 вересня 2023

Оновлено: 7 вересня 2023

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1

Yus, Miguel. "Copper-Catalyzed Asymmetric Synthesis." Current Organic Chemistry 18, no. 15 (September 16, 2014): 2047. http://dx.doi.org/10.2174/138527281815140916093030.

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2

Liu, Nan, Bo Wang, Wenwen Chen, Chulong Liu, Xinyan Wang, and Yuefei Hu. "A general route for synthesis of N-aryl phenoxazines via copper(i)-catalyzed N-, N-, and O-arylations of 2-aminophenols." RSC Adv. 4, no. 93 (2014): 51133–39. http://dx.doi.org/10.1039/c4ra09593f.

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Анотація:

A novel copper(i)-catalyzed tandem reaction ofN- andO-arylations was developed and a general route for synthesis ofN-aryl phenoxazinesviacopper-catalyzedN-,N-, andO-arylations of 2-aminophenols was established.

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3

Depa, Navaneetha, and Harikrishna Erothu. "DESIGN AND SYNTHESIS OF NOVEL PERILLYL-4HPYRANTRIAZOLE DERIVATIVES." Rasayan Journal of Chemistry 15, no. 01 (2022): 302–9. http://dx.doi.org/10.31788/rjc.2022.1516629.

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Анотація:

We report a set of twelve rationally designed and library of perillyl-4H-pyrantriazole derivatives (6a-6l) through a sequence of a multicomponent reaction followed by copper-catalyzed cycloaddition. The intermediate 4-aryl-4Hpyran (4) was obtained by three-component condensation of 5,5-dimethylcyclohexane-1,3-dione) (1), 4-(prop-2-yn1-yloxy) benzaldehyde (2) and malononitrile (3). To this intermediate, azido benzenes (5) were subjected using copper catalyze cycloaddition to produce perillyl-4H-pyrantriazole derivatives in better to good yields. All compounds were validated by mass, 13C-NMR, FTIR and 1H-NMR spectrometry.

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4

Roke, D., M. Fañanás-Mastral, and B. L. Feringa. "Iterative catalyst controlled diastereodivergent synthesis of polypropionates." Organic Chemistry Frontiers 3, no. 11 (2016): 1383–91. http://dx.doi.org/10.1039/c6qo00199h.

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5

Hemming, David, Russell Fritzemeier, Stephen A. Westcott, Webster L. Santos, and Patrick G. Steel. "Copper-boryl mediated organic synthesis." Chemical Society Reviews 47, no. 19 (2018): 7477–94. http://dx.doi.org/10.1039/c7cs00816c.

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6

Lu, Jiaqing, Yuning Man, Yabin Zhang, Bo Lin, Qi Lin, and Zhiqiang Weng. "Copper-catalyzed chemoselective synthesis of 4-trifluoromethyl pyrazoles." RSC Advances 9, no. 53 (2019): 30952–56. http://dx.doi.org/10.1039/c9ra07694h.

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7

Bates, Craig G., Pranorm Saejueng, and D. Venkataraman. "Copper-Catalyzed Synthesis of 1,3-Enynes." Organic Letters 6, no. 9 (April 2004): 1441–44. http://dx.doi.org/10.1021/ol049706e.

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8

Allen, Derek Van, and D. Venkataraman. "Copper-Catalyzed Synthesis of Unsymmetrical Triarylphosphines†." Journal of Organic Chemistry 68, no. 11 (May 2003): 4590–93. http://dx.doi.org/10.1021/jo0343376.

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9

Zheng, Nan, and Stephen L. Buchwald. "Copper-Catalyzed Regiospecific Synthesis ofN-Alkylbenzimidazoles." Organic Letters 9, no. 23 (November 2007): 4749–51. http://dx.doi.org/10.1021/ol7020737.

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10

Jen, Wendy S., Matthew D. Truppo, Deborah Amos, Paul Devine, Michael McNevin, Mirlinda Biba, and Kevin R. Campos. "Copper-Catalyzed Synthesis of Enantioenriched Tetraarylethanes." Organic Letters 10, no. 5 (March 2008): 741–44. http://dx.doi.org/10.1021/ol7027543.

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11

Bates, Craig G., Pranorm Saejueng, Michael Q. Doherty, and D. Venkataraman. "Copper-Catalyzed Synthesis of Vinyl Sulfides." Organic Letters 6, no. 26 (December 2004): 5005–8. http://dx.doi.org/10.1021/ol0477935.

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12

Chassaing, Stefan, Aurélien Alix, Andrea Olmos, Muriel Keller, Jean Sommer, and Patrick Pale. "Metal-doped Zeolites as Green Catalysts for Organic Synthesis." Zeitschrift für Naturforschung B 65, no. 7 (July 1, 2010): 783–90. http://dx.doi.org/10.1515/znb-2010-0703.

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Анотація:

Metal-doped zeolites prepared by vapor diffusion are excellent heterogeneous catalysts. Copper(I)- exchanged zeolites catalyze for example 1,3-dipolar reactions or Mannich condensation, whereas scandium(III)-exchanged zeolites catalyze the Mukaiyama-type aldolization. These catalysts are easily prepared, stable for months, conveniently recovered by filtration and recyclable. They can be used in safe solvents and even without solvent, and thus fully comply with the Green Chemistry principles. Their ease of handling and their large scope of applications enabled us to introduce the “zeo-click” concept for organic synthesis catalyzed by such green heterogeneous catalysts.

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13

Dalpozzo, Renato, and Raffaella Mancuso. "Copper-Catalyzed Synthesis of Coumarins. A Mini-Review." Catalysts 11, no. 11 (November 16, 2021): 1382. http://dx.doi.org/10.3390/catal11111382.

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Анотація:

Coumarin (2H-chromen-2-one) derivatives have important uses in medicinal and synthetic chemistry, for example, as fluorescent probes. These properties have prompted chemists to develop efficient synthetic methods to synthesize the coumarin core and/or to functionalize it. In this context, many metal-catalyzed syntheses of coumarins have been introduced; among them, copper-catalyzed reactions appear to be very promising owing to the non-toxicity and cheapness of copper complexes. In this mini-review, the results in this field are summarized. We hope to stimulate other applications of these complexes in the preparation of coumarin derivatives.

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14

Yang, Lei, Honghua Luo, Yan Sun, Zhenyu Shi, Kaidong Ni, Fei Li, and Dongyin Chen. "A Highly Efficient Copper-Catalyzed Three-Component Synthesis of 4-Aminoquinazolines." Synthesis 49, no. 11 (February 23, 2017): 2535–43. http://dx.doi.org/10.1055/s-0036-1588727.

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Анотація:

A highly efficient copper-catalyzed one-pot protocol is developed for the synthesis of 4-aminoquinazolines from easily available 2-iodo- or 2-bromobenzimidamides, aldehydes, and sodium azide. This one-pot approach proceeds via consecutive copper-catalyzed SNAr substitution, reduction, cyclization, oxidation and tautomerization. The corresponding target products (26 examples) are obtained in 50–90% yield.

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15

Xing, Naiguo, Jiangkun Huang, Peng Wang, Lan Luo, Shilong Zheng, and Ling He. "Novel one-pot synthesis of imidazolinones from esters: a concise synthesis of GSK2137305." Organic & Biomolecular Chemistry 18, no. 11 (2020): 2175–81. http://dx.doi.org/10.1039/c9ob02743b.

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16

Gong, Xinchi, Zhengqi Shen, Ganghu Wang, Lingling Qu, and Chunyin Zhu. "Heterogeneous copper-catalyzed synthesis of diaryl sulfones." Organic & Biomolecular Chemistry 19, no. 48 (2021): 10662–68. http://dx.doi.org/10.1039/d1ob01830b.

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17

Reinus, Brandon J., and Sean M. Kerwin. "N-Alkynyl Pyrrole Based Total Synthesis of Shensongine A." Synthesis 51, no. 21 (August 12, 2019): 4085–105. http://dx.doi.org/10.1055/s-0037-1611904.

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Анотація:

A copper-catalyzed N-alkynylation of pyrrole and a gold-catalyzed spiroketalization were key steps in the total synthesis of the pyrrole spiroketal alkaloid shensongine A. The preparation of this alkaloid is concise and amenable to the rapid synthesis of a diverse library of compounds.

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18

Wang, Haifeng, Xiangli Sun, Shuangling Zhang, Guanglu Liu, Chunjie Wang, Lili Zhu, and Hui Zhang. "Efficient Copper-Catalyzed Synthesis of Substituted Pyrazoles at Room Temperature." Synlett 29, no. 20 (November 15, 2018): 2689–92. http://dx.doi.org/10.1055/s-0037-1610330.

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Анотація:

An efficient method for the synthesis of pyrazoles through a copper-catalyzed condensation reaction has been developed. The new catalytic system not only maintained a broad substrate scope but was also active under acid-free reaction conditions, overcoming the conventional requirement for an acid-catalyzed system. Furthermore, the copper catalyst enabled this reaction to be performed at room temperature and in a short reaction time.

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19

Chun, Candy K. Y., and Richard J. Payne. "Synthesis of MUC1 Peptide and Glycopeptide Dendrimers." Australian Journal of Chemistry 62, no. 10 (2009): 1339. http://dx.doi.org/10.1071/ch09282.

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Анотація:

Several dendrimers possessing multiple copies of peptides and glycopeptides belonging to the MUC1 eicosapeptide tandem repeat sequence have been prepared. Fmoc-strategy solid-phase peptide synthesis was used to construct the peptides and glycopeptides, which were conjugated to suitably functionalized dendrimer cores using the copper-catalyzed azide-alkyne cycloaddition reaction to produce multivalent peptide and glycopeptide dendrimers.

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20

Wen, Qiaodong, Ping Lu, and Yanguang Wang. "Copper-mediated three-component synthesis of 3-cyanoimidazo[1,2-a]pyridines." Chemical Communications 51, no. 84 (2015): 15378–81. http://dx.doi.org/10.1039/c5cc05821j.

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Анотація:

A copper-mediated three-component approach towards the synthesis of 3-cyanoimidazo[1,2-a]pyridines from 2-aminopyridines, acetophenones and benzyl cyanide was developed. This cascade reaction proceeds through a copper-mediated oxidative release of cyanide from benzyl cyanide, a copper-mediated Ortoleva–King reaction, and a copper-catalyzed cyanation.

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21

Bakherad, Mohammad, Ali Keivanloo, Amir H. Amin, and Amir Farkhondeh. "Synthesis of 1,2,3 triazole-linked benzimidazole through a copper-catalyzed click reaction." Heterocyclic Communications 25, no. 1 (November 28, 2019): 122–29. http://dx.doi.org/10.1515/hc-2019-0016.

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Анотація:

AbstractAn efficient method has been developed for the synthesis of 1,2,3 triazole-linked benzimidazole through a copper-catalyzed click reaction in ethanol at 50°C. A broad range of aromatic azides were successfully reacted with n-propynylated benzimidazole via copper-catalyzed azide-alkyne cycloaddition reactions in the absence of a ligand. This method offers many advantages including short reaction times, low cost, and simple purification procedures.

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22

Pünner, Florian, Yoshihiro Sohtome, and Mikiko Sodeoka. "Solvent-dependent copper-catalyzed synthesis of pyrazoles under aerobic conditions." Chemical Communications 52, no. 98 (2016): 14093–96. http://dx.doi.org/10.1039/c6cc06935e.

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23

Whiting, Andrew, and Jing-Biao Chen. "Recent Advances in Copper-Catalyzed Asymmetric Hydroboration of Electron-Deficient Alkenes: Methodologies and Mechanism." Synthesis 50, no. 19 (July 23, 2018): 3843–61. http://dx.doi.org/10.1055/s-0037-1609583.

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Анотація:

The efficient synthesis of enantioenriched organoboron compounds has been recognized as an important topic in recent years. As an update review, this article aims to select key achievements in copper-catalyzed, electron-deficient alkene enantioselective hydroboration methodologies since the beginning of 2017. In addition, it covers relevant mechanistic investigations developed over the last six years, as well as total synthesis applications for preparing 1,3-diols as important medicinal intermediates.1 Introduction2 Methodologies for Copper-Catalyzed Hydroboration2.1 α,β-Unsaturated Ketones and Imines2.2 α,β-Unsaturated Esters and Cyanides2.3 Aryl Alkenes and Alkyl Alkenes3 Mechanistic Investigations on the Copper-Catalyzed Hydroboration3.1 A Cu–BX2 Intermediate3.1.1 Experimental Analysis3.1.2 Borylative Difunctionalization Methodologies3.1.3 Density Functional Theory3.2 A Cu–H Intermediate3.3 Other Mechanistic Proposals4 Synthetic Applications: Chiral 1,3-Diols5 Conclusions and Outlook

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24

Lou, Zhenbang, Ningning Man, Haijun Yang, Changjin Zhu, and Hua Fu. "Copper-Catalyzed Cascade Synthesis of [1,2,4]-Triazoloquinazolinones." Synlett 29, no. 10 (April 20, 2018): 1395–99. http://dx.doi.org/10.1055/s-0036-1591565.

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An efficient and practical method for the synthesis of 1,2,4-triazolo[5,1-b]quinazolin-9(3H)-ones has been developed via the copper-catalyzed domino reactions of readily available substituted N′-acetyl-2-bromobenzohydrazides with cyanamide. The protocol uses inexpensive CuI as the catalyst, and no other ligand or additive was required. The target products were prepared in good to excellent yields with tolerance of various functional groups.

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25

Kaewmee, Benyapa, Vatcharin Rukachaisirikul, and Juthanat Kaeobamrung. "Synthesis of quinolines via copper-catalyzed domino reactions of enaminones." Organic & Biomolecular Chemistry 15, no. 35 (2017): 7387–95. http://dx.doi.org/10.1039/c7ob01867c.

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26

Huang, Huawen, Lichang Tang, Jinhui Cai, and Guo-Jun Deng. "Mild and ambient annulations for pyrrole synthesis from amines and arylacetaldehydes." RSC Advances 6, no. 9 (2016): 7011–14. http://dx.doi.org/10.1039/c5ra24006a.

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27

Zhang, Jianbo, Youxian Dong, Madina Yuma, Yuling Mei, Nan Jiang, Guofang Yang, and Zhongfu Wang. "Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides." Synlett 31, no. 11 (May 5, 2020): 1087–93. http://dx.doi.org/10.1055/s-0040-1707098.

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Анотація:

An efficient glycosylation method to synthesize 2-deoxy-O-galactosides based on a Cu(II)-catalyzed reaction without additional ligand has been developed. The glycosylation was amenable to different protected glycal donors and a wide range of acceptors including alcohols, amino acids, sugars, and phenol, and proceeds with excellent yield and high α-selectivity under mild conditions. The reaction proceeds readily on a gram scale, and its versatility is exemplified in the synthesis of oligosaccharides.

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28

Ji, Wangqin, Hai-Hong Wu, Wenbo Li, and Junliang Zhang. "Copper-catalyzed cyclization reaction: synthesis of trifluoromethylated indolinyl ketones." Chemical Communications 57, no. 36 (2021): 4448–51. http://dx.doi.org/10.1039/d1cc00960e.

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29

Jana, Sadhan, Athira Ashokan, Shailesh Kumar, Ajay Verma, and Sangit Kumar. "Copper-catalyzed trifluoromethylation of alkenes: synthesis of trifluoromethylated benzoxazines." Organic & Biomolecular Chemistry 13, no. 31 (2015): 8411–15. http://dx.doi.org/10.1039/c5ob01196e.

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30

Zeng, Weilan, Pan Dang, Xiaoyun Zhang, Yun Liang, and Caiyun Peng. "Copper-catalyzed synthesis of 2-aminobenzothiazoles from carbodiimide and sodium hydrosulfide." RSC Adv. 4, no. 59 (2014): 31003–6. http://dx.doi.org/10.1039/c4ra04047c.

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31

Wang, Jinjin, Ping Lu, and Yanguang Wang. "Copper-catalyzed multi-component synthesis of acrylamidines and benzoimidazoles." Organic Chemistry Frontiers 2, no. 10 (2015): 1346–51. http://dx.doi.org/10.1039/c5qo00196j.

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32

Harkat, Hassina, Sophie Borghèse, Matteo De Nigris, Serguei Kiselev, Valérie Bénéteau, and Patrick Pale. "Zeo-Click Synthesis: Copper-Zeolite-Catalyzed Synthesis of Ynamides." Advanced Synthesis & Catalysis 356, no. 18 (November 21, 2014): 3842–48. http://dx.doi.org/10.1002/adsc.201400189.

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33

Altarejos, Julia, David Sucunza, Juan J. Vaquero, and Javier Carreras. "Enantioselective Copper-Catalyzed Synthesis of Trifluoromethyl-Cyclopropylboronates." Organic Letters 23, no. 15 (July 28, 2021): 6174–78. http://dx.doi.org/10.1021/acs.orglett.1c02420.

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34

Yavari, Issa, Majid Ghazanfarpour-Darjani, and Yazdan Solgi. "A Copper-Catalyzed Synthesis of Symmetrical Diarylsulfanes." Synlett 25, no. 08 (April 10, 2014): 1121–23. http://dx.doi.org/10.1055/s-0033-1340985.

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35

Shi, Liangliang, Ruji Wang, Haijun Yang, Yuyang Jiang, and Hua Fu. "Efficient copper-catalyzed domino synthesis of tetrazoloisoquinolines." RSC Advances 3, no. 18 (2013): 6278. http://dx.doi.org/10.1039/c3ra23230a.

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36

Fu, Hua, and Tao Liu. "Copper-Catalyzed Synthesis of N-Heterocyclic Compounds." Synthesis 44, no. 18 (August 13, 2012): 2805–24. http://dx.doi.org/10.1055/s-0032-1316763.

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37

Song, Wang-Ze, Jun-Hao Li, Ming Li, Jun-Nan He, Kun Dong, Karim Ullah, and Yu-Bin Zheng. "Copper-catalyzed one-pot synthesis of alkynylphophonates." Synthetic Communications 49, no. 5 (February 6, 2019): 697–703. http://dx.doi.org/10.1080/00397911.2019.1566474.

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38

"Copper-Catalyzed Isoxazole Synthesis." Synfacts 18, no. 10 (September 20, 2022): 1065. http://dx.doi.org/10.1055/s-0042-1752979.

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39

Rao, Maddali L. N., Sk Shamim Islam, and Priyabrata Dasgupta. "Copper-catalyzed domino synthesis of ynamines." Organic & Biomolecular Chemistry, 2021. http://dx.doi.org/10.1039/d1ob01383a.

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Анотація:

A Cu-catalyzed domino protocol using gem-dibromoalkenes and N-heteroarenes is developed for the synthesis of ynamines and it is applied in the synthesis of enynamines, bis/tris-ynamines and peyonine natural product.

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40

"Copper-Catalyzed Synthesis of Isoxazoles." Synfacts 2010, no. 02 (January 21, 2010): 0154. http://dx.doi.org/10.1055/s-0029-1219115.

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41

"Copper-Catalyzed Synthesis of Imidazopyridines." Synfacts 11, no. 08 (July 20, 2015): 0800. http://dx.doi.org/10.1055/s-0034-1378800.

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42

"Copper-Catalyzed Synthesis of Dibenzodiazepinones." Synfacts 10, no. 11 (October 20, 2014): 1141. http://dx.doi.org/10.1055/s-0034-1379348.

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43

"Copper-Catalyzed Synthesis of Quinazolinones." Synfacts 12, no. 12 (November 17, 2016): 1234. http://dx.doi.org/10.1055/s-0036-1589658.

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44

Glueck, David S. "Catalytic Asymmetric Synthesis of P-Stereogenic Phosphines: Beyond Precious Metals." Synlett, October 13, 2020. http://dx.doi.org/10.1055/s-0040-1707309.

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Анотація:

AbstractMetal-catalyzed asymmetric synthesis of P-stereogenic phosphines is a potentially useful approach to a class of chiral ligands with valuable applications in asymmetric catalysis. We introduced this idea with chiral platinum and palladium catalysts, exploiting rapid pyramidal inversion in diastereomeric metal–phosphido complexes (ML*(PRR′)) to control phosphorus stereochemistry. This Account summarizes our attempts to develop related synthetic methods using earth-abundant metals, especially copper, in which weaker metal–ligand bonds and faster substitution processes were expected to result in more active catalysts. Indeed, precious metals were not required. Without any transition metals at all, we exploited related P-epimerization processes to prepare enantiomerically pure phosphiranes and secondary phosphine oxides (SPOs) from commercially available chiral epoxides.1 Introduction2 Copper-Catalyzed Phosphine Alkylation3 Copper-Catalyzed Tandem Phosphine Alkylation/Arylation4 Nickel-Catalyzed Phosphine Alkylation5 Proton-Mediated P-Epimerization in Synthesis of Chiral Phosphiranes6 Diastereoselective Synthesis of P-Stereogenic Secondary Phosphine Oxides (SPOs) from (+)-Limonene Oxide7 Conclusions

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45

Hisana, Kalathingal Nasreen, C. M. A. Afsina, and Gopinathan Anilkumar. "Copper-catalyzed N-arylation of pyrroles: an overview." New Journal of Chemistry, 2021. http://dx.doi.org/10.1039/d1nj02638k.

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Анотація:

The copper-catalyzed N-arylation of pyrroles has attracted great attention in organic synthesis due to its wide applications in medicinal chemistry, natural products, etc. Here, we summarize the overall advances in the copper-catalyzed C–N cross-coupling of pyrroles with aryl halides.

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46

"Copper-Catalyzed Synthesis of Thioamide Peptides." Synfacts 18, no. 02 (January 18, 2022): 0220. http://dx.doi.org/10.1055/s-0041-1737520.

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47

"A Copper-Catalyzed Synthesis of Azoheteroarenes." Synfacts 17, no. 08 (July 20, 2021): 0903. http://dx.doi.org/10.1055/s-0040-1720375.

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48

"Copper-Catalyzed Domino Synthesis of Indoles." Synfacts 2009, no. 08 (July 23, 2009): 0836. http://dx.doi.org/10.1055/s-0029-1217448.

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49

"Copper-Catalyzed Synthesis of 1,2,4-Triazoles." Synfacts 2010, no. 01 (December 21, 2009): 0021. http://dx.doi.org/10.1055/s-0029-1218467.

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"Copper-Catalyzed Synthesis of Sulfonylated Oxindoles." Synfacts 10, no. 11 (October 20, 2014): 1142. http://dx.doi.org/10.1055/s-0034-1379350.

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