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Journal articles on the topic 'Asymmetric suzuki miyaura'

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Author: Grafiati

Published: 23 September 2022

Last updated: 28 September 2022

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1

Haraguchi, Ryosuke, Shun Hoshino, Tatsuro Yamazaki, and Shin-ichi Fukuzawa. "Chiral triazolylidene-Pd-PEPPSI: synthesis, characterization, and application in asymmetric Suzuki–Miyaura cross-coupling." Chemical Communications 54, no. 17 (2018): 2110–13. http://dx.doi.org/10.1039/c7cc09960f.

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2

Vinci, Daniele, Nelson Martins, Ourida Saidi, John Bacsa, Amadeu Brigas, and Jianliang Xiao. "Ferrocenyl phosphine–oxazaphospholidine oxide ligands for the Suzuki–Miyaura coupling of hindered aryl bromides and chlorides." Canadian Journal of Chemistry 87, no. 1 (January 1, 2009): 171–75. http://dx.doi.org/10.1139/v08-113.

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A series of ferrocenyl oxazaphospholidine phosphines that differ electronically and sterically were investigated as ligands for the Suzuki–Miyaura cross-coupling reactions. One of these compounds, 1, was shown to be highly effective in the coupling reactions of bulky aryl bromides with boronic acids when combined with Pd(OAc)2, while another, 2, was capable of coupling aryl chlorides with boronic acids. However, these ligands were less effective in asymmetric induction.Key words: Suzuki–Miyaura coupling, ferrocenyl phosphines, aryl bromides, aryl chlorides, palladium.

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3

van Dijk, Lucy, and Stephen P. Fletcher. "Rh-catalyzed asymmetric Suzuki-Miyaura cross-coupling." Trends in Chemistry 3, no. 9 (September 2021): 795–96. http://dx.doi.org/10.1016/j.trechm.2021.05.007.

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4

Xia, Wang, Zhen-Wei Zhang, Yongsu Li, Xiaoding Jiang, Hao Liang, Yaqi Zhang, Rihui Cao, and Liqin Qiu. "Enantioselective synthesis of chiral heterocyclic biaryls via asymmetric Suzuki–Miyaura cross-coupling of 3-bromopyridine derivatives." Organic & Biomolecular Chemistry 17, no. 9 (2019): 2351–55. http://dx.doi.org/10.1039/c8ob03048k.

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5

Zhang, Dao, Yu He, and Junkai Tang. "Chiral linker-bridged bis-N-heterocyclic carbenes: design, synthesis, palladium complexes, and catalytic properties." Dalton Transactions 45, no. 29 (2016): 11699–709. http://dx.doi.org/10.1039/c6dt00984k.

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6

Liang, Xu, Yuanyuan Qiu, Xifeng Zhang, and Weihua Zhu. "The post-functionalization of Co(iii)PPh3 triarylcorroles through Suzuki–Miyaura couplings and their tunable electrochemically-catalyzed hydrogen evolution and oxygen reduction." Dalton Transactions 49, no. 10 (2020): 3326–32. http://dx.doi.org/10.1039/c9dt04917g.

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The post-functionalization of six novel symmetric and asymmetric meso-expanded Co(iii) corroles through Suzuki–Miyaura coupling reactions has been successfully accomplished and is reported along with their structural characterization.

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7

Chen, Peng, Liang Huo, Huilin Li, Lin Liu, Ziyun Yuan, Hao Zhang, Shangbiao Feng, Xingang Xie, Xiaolei Wang, and Xuegong She. "Bioinspired total synthesis of (−)-gymnothelignan L." Organic Chemistry Frontiers 5, no. 7 (2018): 1124–28. http://dx.doi.org/10.1039/c8qo00026c.

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The first asymmetric total synthesis of gymnothelignan L has been accomplished in 14 steps with 11.2% overall yield. The synthetic approach features an anti Evans aldol reaction, a diastereoselective methylation, a Suzuki–Miyaura coupling and a bioinspired desymmetric transannular Friedel–Crafts reaction.

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8

Nagata, Yuuya, Takuma Kuroda, Keisuke Takagi, and Michinori Suginome. "Ether solvent-induced chirality inversion of helical poly(quinoxaline-2,3-diyl)s containing l-lactic acid derived side chains." Chem. Sci. 5, no. 12 (2014): 4953–56. http://dx.doi.org/10.1039/c4sc01920b.

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Poly(quinoxaline-2,3-diyl) bearing PPh₂ pendants along with chiral side chains derived from l-lactic acid exhibited induction of pure M- and P-helical conformations in 1,2-dimethoxyethane and t-butyl methyl ether, respectively, affording enantiomeric products in asymmetric Suzuki–Miyaura reaction.

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9

Akai, Yuto, Laure Konnert, Takeshi Yamamoto, and Michinori Suginome. "Asymmetric Suzuki–Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos." Chemical Communications 51, no. 33 (2015): 7211–14. http://dx.doi.org/10.1039/c5cc01074h.

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Axially chiral 1,1′-biaryl-2-carboxylates were synthesized via Suzuki–Miyaura cross-coupling of 2,4-dimethylpentan-3-yl 1-halo-2-naphthoates with arylboronic acids with single-handed helical polymer ligands PQXphos.

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10

Babu, K., Arramshetti Venkanna, Borra Poornima, Bandi Siva, and B. Babu. "Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core." Synlett 29, no. 07 (February 19, 2018): 908–11. http://dx.doi.org/10.1055/s-0036-1591539.

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A stereoselective synthesis of the dibenzocyclooctadiene lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

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11

Kučera, Roman, F. Wieland Goetzke, and Stephen P. Fletcher. "An Asymmetric Suzuki–Miyaura Approach to Prostaglandins: Synthesis of Tafluprost." Organic Letters 22, no. 8 (March 27, 2020): 2991–94. http://dx.doi.org/10.1021/acs.orglett.0c00745.

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12

Pareek, Monika, and Raghavan B. Sunoj. "Energetics of Dynamic Kinetic Asymmetric Transformation in Suzuki–Miyaura Coupling." ACS Catalysis 10, no. 7 (March 16, 2020): 4349–60. http://dx.doi.org/10.1021/acscatal.9b05526.

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13

Tang, Wenjun, Nitinchandra D. Patel, Guangqing Xu, Xiaobing Xu, Jolaine Savoie, Shengli Ma, Ming-Hong Hao, et al. "Efficient Chiral Monophosphorus Ligands for Asymmetric Suzuki–Miyaura Coupling Reactions." Organic Letters 14, no. 9 (April 12, 2012): 2258–61. http://dx.doi.org/10.1021/ol300659d.

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14

Suginome, Michinori, Takeshi Yamamoto, Yuuya Nagata, Tetsuya Yamada, and Yuto Akai. "Catalytic asymmetric synthesis using chirality-switchable helical polymer as a chiral ligand." Pure and Applied Chemistry 84, no. 8 (February 3, 2012): 1759–69. http://dx.doi.org/10.1351/pac-con-11-08-23.

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Single-handed PQXphos, i.e., helical poly(quinoxaline-2,3-diyl)s bearing diarylphosphino pendant groups, served as remarkable chiral ligands in palladium-catalyzed asymmetric hydrosilylation of styrenes and asymmetric biaryl synthesis by Suzuki–Miyaura coupling, affording up to 98 % enantiomeric excess (e.e.) in both reactions. A palladium complex of high-molecular-weight variant (1000mer) of PQXphos could be reused eight times by virtue of the formation of an insoluble polymer complex. PQXphos underwent solvent-dependent inversion of the helical sense, enabling production of either of two enantiomeric products using a single PQXphos.

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15

Tang, Yao, Shengzhou Jin, Sai Zhang, Guan-Zhao Wu, Jia-Yin Wang, Ting Xu, Yu Wang, et al. "Multilayer 3D Chiral Folding Polymers and Their Asymmetric Catalytic Assembly." Research 2022 (February 16, 2022): 1–8. http://dx.doi.org/10.34133/2022/9847949.

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A novel class of polymers and oligomers of chiral folding chirality has been designed and synthesized, showing structurally compacted triple-column/multiple-layer frameworks. Both uniformed and differentiated aromatic chromophoric units were successfully constructed between naphthyl piers of this framework. Screening monomers, catalysts, and catalytic systems led to the success of asymmetric catalytic Suzuki-Miyaura polycouplings. Enantio- and diastereochemistry were unambiguously determined by X-ray structural analysis and concurrently by comparison with a similar asymmetric induction by the same catalyst in the asymmetric synthesis of a chiral three-layered product. The resulting chiral polymers exhibit intense fluorescence activity in a solid form and solution under specific wavelength irradiation.

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16

Thennakoon, Nishani, Gurpreet Kaur, Jingjing Wang, Paul G. Plieger, and Gareth J. Rowlands. "An Asymmetric Variant of the Bischler–Möhlau Indole Synthesis." Australian Journal of Chemistry 68, no. 4 (2015): 566. http://dx.doi.org/10.1071/ch14548.

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Enantiomerically enriched planar chiral indoles were prepared by an asymmetric variant of the Bischler–Möhlau synthesis. Cinchonine was used as a ‘traceless’ resolving reagent, allowing the formation of readily separable quaternary ammonium salts that were the key intermediates in the indole synthesis. The condensation of the ammonium salt and various substituted anilines was achieved under microwave irradiation; this reduced reaction times and minimised racemisation. The utility of the indoles was demonstrated by their transformation into monophosphane ligands that were capable of coupling challenging substrates in the Suzuki–Miyaura reaction.

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17

Liu, Lian-jun, Feijun Wang, Wenfeng Wang, Mei-xin Zhao, and Min Shi. "Synthesis of chiral mono(N-heterocyclic carbene) palladium and gold complexes with a 1,1'-biphenyl scaffold and their applications in catalysis." Beilstein Journal of Organic Chemistry 7 (May 4, 2011): 555–64. http://dx.doi.org/10.3762/bjoc.7.64.

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Axially chiral mono(NHC)–Pd(II) and mono(NHC)–Au(I) complexes with one side shaped 1,1'-biphenyl backbone have been prepared from chiral 6,6'-dimethoxybiphenyl-2,2'-diamine. The complexes were characterized by X-ray crystal structure diffraction. The Pd(II) complex showed good catalytic activities in the Suzuki–Miyaura and Heck–Mizoroki coupling reactions, and the (S)-Au(I) complexes also showed good catalytic activities in the asymmetric intramolecular hydroamination reaction to give the corresponding product in moderate ee.

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18

Xu, Guangqing, Qing Zhao, and Wenjun Tang. "Development of Efficient Asymmetric Suzuki-Miyaura Cross-Coupling and Applications in Synthesis." Chinese Journal of Organic Chemistry 34, no. 10 (2014): 1919. http://dx.doi.org/10.6023/cjoc201406030.

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19

Tang, Wenjun, and et al et al. "ChemInform Abstract: Efficient Chiral Monophosphorus Ligands for Asymmetric Suzuki-Miyaura Coupling Reactions." ChemInform 43, no. 34 (July 26, 2012): no. http://dx.doi.org/10.1002/chin.201234082.

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20

Zhou, Yougui, Shouliang Wang, Wenhao Wu, Qing Li, Yuwei He, Yue Zhuang, Lanning Li, Jiyan Pang, Zhongyuan Zhou, and Liqin Qiu. "Enantioselective Synthesis of Axially Chiral Multifunctionalized Biaryls via Asymmetric Suzuki–Miyaura Coupling." Organic Letters 15, no. 21 (October 18, 2013): 5508–11. http://dx.doi.org/10.1021/ol402666p.

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21

Ros, Abel, Beatriz Estepa, Antonio Bermejo, Eleuterio Álvarez, Rosario Fernández, and José M. Lassaletta. "Phosphino Hydrazones as Suitable Ligands in the Asymmetric Suzuki–Miyaura Cross-Coupling." Journal of Organic Chemistry 77, no. 10 (April 26, 2012): 4740–50. http://dx.doi.org/10.1021/jo300548z.

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22

Tang, Wenjun, Guodu Liu, Guangqing Xu, and Renshi Luo. "Search for Ideal P-Chiral Phosphorus Ligands for Practical Asymmetric Hydrogenation and Asymmetric Suzuki–Miyaura Coupling." Synlett 24, no. 19 (September 23, 2013): 2465–71. http://dx.doi.org/10.1055/s-0033-1339875.

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23

Li, Yongsu, Bendu Pan, Xuefeng He, Wang Xia, Yaqi Zhang, Hao Liang, Chitreddy V. Subba Reddy, Rihui Cao, and Liqin Qiu. "Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position." Beilstein Journal of Organic Chemistry 16 (May 11, 2020): 966–73. http://dx.doi.org/10.3762/bjoc.16.85.

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Pd-catalyzed asymmetric Suzuki–Miyaura couplings of 3-methyl-2-bromophenylamides, 3-methyl-2-bromo-1-nitrobenzene and 1-naphthaleneboronic acids have been successfully developed and the corresponding axially chiral biaryl compounds were obtained in very high yields (up to 99%) with good enantioselectivities (up to 88% ee) under mild conditions. The chiral-bridged biphenyl monophosphine ligands developed by our group exhibit significant superiority to the naphthyl counterpart MOP in both reactivity and enantioselectivity control. The large steric hindrance from π-conjugated ortho-substituents of the bromobenzene substrates and the Pd···O interaction between carbonyl and palladium seem essential to achieve high enantioselectivity.

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24

Castillo, Angelica Balanta, Bernabé F. Perandones, Ennio Zangrando, Serafino Gladiali, Cyril Godard, and Carmen Claver. "Pd-catalysed asymmetric Suzuki–Miyaura reactions using chiral mono- and bidentate phosphorus ligands." Journal of Organometallic Chemistry 743 (October 2013): 31–36. http://dx.doi.org/10.1016/j.jorganchem.2013.06.022.

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25

Sawai, Koji, Ryouta Tatumi, Tsukasa Nakahodo, and Hisashi Fujihara. "Asymmetric Suzuki-Miyaura Coupling Reactions Catalyzed by Chiral Palladium Nanoparticles at Room Temperature." Angewandte Chemie 120, no. 36 (August 1, 2008): 7023–25. http://dx.doi.org/10.1002/ange.200802174.

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26

Sawai, Koji, Ryouta Tatumi, Tsukasa Nakahodo, and Hisashi Fujihara. "Asymmetric Suzuki-Miyaura Coupling Reactions Catalyzed by Chiral Palladium Nanoparticles at Room Temperature." Angewandte Chemie International Edition 47, no. 36 (August 25, 2008): 6917–19. http://dx.doi.org/10.1002/anie.200802174.

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27

Bermejo, Antonio, Abel Ros, Rosario Fernández, and José M. Lassaletta. "C2-Symmetric Bis-Hydrazones as Ligands in the Asymmetric Suzuki−Miyaura Cross-Coupling." Journal of the American Chemical Society 130, no. 47 (November 26, 2008): 15798–99. http://dx.doi.org/10.1021/ja8074693.

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28

Hoang, Gia L., Zhao-Di Yang, Sean M. Smith, Rhitankar Pal, Judy L. Miska, Damaris E. Pérez, Libbie S. W. Pelter, Xiao Cheng Zeng, and James M. Takacs. "Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki–Miyaura Cross-Coupling." Organic Letters 17, no. 4 (February 2, 2015): 940–43. http://dx.doi.org/10.1021/ol503764d.

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29

Benhamou, Laure, Céline Besnard, and E. Peter Kündig. "Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki–Miyaura Coupling Reactions." Organometallics 33, no. 1 (December 16, 2013): 260–66. http://dx.doi.org/10.1021/om4009982.

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30

Dorta, Reto, Linglin Wu, Alvaro Salvador, Arnold Ou, Ming Shi, and Brian Skelton. "Monodentate Chiral N-Heterocyclic Carbene-Palladium-Catalyzed Asymmetric Suzuki-Miyaura and Kumada Coupling." Synlett 24, no. 10 (May 17, 2013): 1215–20. http://dx.doi.org/10.1055/s-0033-1338864.

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31

Jumde, Varsha R., and Anna Iuliano. "Deoxycholic acid derived monophosphites as chiral ligands in the asymmetric Suzuki–Miyaura cross-coupling." Tetrahedron: Asymmetry 22, no. 24 (December 2011): 2151–55. http://dx.doi.org/10.1016/j.tetasy.2011.12.006.

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32

Urbaneja, Xavier, Audrey Mercier, Céline Besnard, and E. Peter Kündig. "Highly efficient desymmetrisation of a tricarbonylchromium 1,4-dibromonaphthalene complex by asymmetric Suzuki–Miyaura coupling." Chemical Communications 47, no. 13 (2011): 3739. http://dx.doi.org/10.1039/c1cc10347d.

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33

Genov, Miroslav, Antonio Almorín, and Pablo Espinet. "Microwave assisted asymmetric Suzuki-Miyaura and Negishi cross-coupling reactions: synthesis of chiral binaphthalenes." Tetrahedron: Asymmetry 18, no. 5 (March 2007): 625–27. http://dx.doi.org/10.1016/j.tetasy.2007.03.001.

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34

Ros, Abel, Beatriz Estepa, Antonio Bermejo, Eleuterio Alvarez, Rosario Fernandez, and Jose M. Lassaletta. "ChemInform Abstract: Phosphino Hydrazones as Suitable Ligands in the Asymmetric Suzuki-Miyaura Cross-Coupling." ChemInform 43, no. 36 (August 9, 2012): no. http://dx.doi.org/10.1002/chin.201236038.

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35

Qiu, Liqin, and et al et al. "ChemInform Abstract: Enantioselective Synthesis of Axially Chiral Multifunctionalized Biaryls via Asymmetric Suzuki-Miyaura Coupling." ChemInform 45, no. 12 (March 6, 2014): no. http://dx.doi.org/10.1002/chin.201412084.

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36

van Dijk, Lucy, Ruchuta Ardkhean, Mireia Sidera, Sedef Karabiyikoglu, Özlem Sari, Timothy D. W. Claridge, Guy C. Lloyd-Jones, Robert S. Paton, and Stephen P. Fletcher. "Mechanistic investigation of Rh(i)-catalysed asymmetric Suzuki–Miyaura coupling with racemic allyl halides." Nature Catalysis 4, no. 4 (April 2021): 284–92. http://dx.doi.org/10.1038/s41929-021-00589-y.

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37

Liu, Guodu, Guangqing Xu, Renshi Luo, and Wenjun Tang. "ChemInform Abstract: Search for Ideal P-Chiral Phosphorus Ligands for Practical Asymmetric Hydrogenation and Asymmetric Suzuki-Miyaura Coupling." ChemInform 45, no. 9 (February 14, 2014): no. http://dx.doi.org/10.1002/chin.201409259.

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38

Zhao, Meng, Gang Zhang, Jingmiao Zhang, Shan Huang, Xiuxia Liu, and Fei Li. "Crystal structure of 4-(anthracen-9-yl)pyridine." Acta Crystallographica Section E Crystallographic Communications 77, no. 6 (May 11, 2021): 605–8. http://dx.doi.org/10.1107/s2056989021004710.

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The title compound, C19H13N, which crystallizes in the monoclinic C2/c space group with one half-molecule in the asymmetric unit, was synthesized by Suzuki–Miyaura cross-coupling reaction of 9-bromoanthracene with pyridin-4-ylboronic acid and purified by column chromatography on silica gel. Light-yellow crystals of 4-(anthracen-9-yl)-pyridine suitable for X-ray diffraction were collected by the solvent evaporation method. In the crystal, pairs of molecules are connected by intermolecular C—H...π (pyridine) interactions [d(H7...Cg) = 2.7391 (2) Å], forming cyclic centrosymmetric dimers, further resulting in an infinite one-dimensional linear chain along the c-axis direction. Weak face-to-face π–π stacking interactions [d(Cg...Cg) = 3.6061 (2) Å] link neighboring lamellar networks into the supramolecular structure.

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39

Xu, Guangqing, Wenzhen Fu, Guodu Liu, Chris H. Senanayake, and Wenjun Tang. "Efficient Syntheses of Korupensamines A, B and Michellamine B by Asymmetric Suzuki-Miyaura Coupling Reactions." Journal of the American Chemical Society 136, no. 2 (October 28, 2013): 570–73. http://dx.doi.org/10.1021/ja409669r.

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40

Wu, Linglin, Alvaro Salvador, Arnold Ou, Ming Wen Shi, Brian W. Skelton, and Reto Dorta. "ChemInform Abstract: Monodentate Chiral N-Heterocyclic Carbene-Palladium-Catalyzed Asymmetric Suzuki-Miyaura and Kumada Coupling." ChemInform 44, no. 40 (September 12, 2013): no. http://dx.doi.org/10.1002/chin.201340092.

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41

Balanta Castillo, Angelica, Bernabe F. Perandones, Ennio Zangrando, Serafino Gladiali, Cyril Godard, and Carmen Claver. "ChemInform Abstract: Pd-Catalyzed Asymmetric Suzuki-Miyaura Reactions Using Chiral Mono- and Bidentate Phosphorus Ligands." ChemInform 45, no. 4 (January 3, 2014): no. http://dx.doi.org/10.1002/chin.201404033.

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42

Mikami, Koichi, Takashi Miyamoto, and Manabu Hatano. "A highly efficient asymmetric Suzuki–Miyaura coupling reaction catalyzed by cationic chiral palladium(ii) complexes." Chem. Commun., no. 18 (2004): 2082–83. http://dx.doi.org/10.1039/b407250b.

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43

Hoang, Gia L., Zhao-Di Yang, Sean M. Smith, Rhitankar Pal, Judy L. Miska, Damaris E. Perez, Libbie S. W. Pelter, Xiao Cheng Zeng, and James M. Takacs. "ChemInform Abstract: Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki-Miyaura Cross-Coupling." ChemInform 46, no. 28 (June 25, 2015): no. http://dx.doi.org/10.1002/chin.201528116.

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44

Ishikawa, Yoshinobu, Takafumi Suzuki, and Nanako Yoshida. "3-Acetyl-2-fluoro-6H-benzo[c]chromen-6-one." Acta Crystallographica Section E Structure Reports Online 70, no. 4 (March 26, 2014): o470—o471. http://dx.doi.org/10.1107/s1600536814005959.

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The title compound, C15H9FO3, was obtained in a one-pot synthesis by Suzuki–Miyaura cross-coupling and nucleophilic substitution reaction of 4′-chloro-2′,5′-difluoroacetophenone witho-(methoxycarbonyl)phenylboronic acid. The asymmetric unit contains two crystallographically independent molecules related by a non-crystallographic inversion centre. There are face-to-face stacking interactions between the aromatic rings of the benzoate and acetophenone units of the symmetry-independent molecules [centroid–centroid distances = 3.870 (3) and 3.986 (3) Å]. In the crystal, molecules are further assembledviastacking interactions along thea-axis direction. One of the molecules interacts with its inversion equivalent [centroid–centroid distance between the aromatic rings of the benzoate and acetophenone units = 3.932 (3) Å], and the other interacts with its twofold axis equivalent [centroid–centroid distance between the aromatic rings of acetophenone units = 3.634 (3) Å].

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45

Jasiński, Radomir, Oleg M. Demchuk, and Dmytro Babyuk. "A Quantum-Chemical DFT Approach to Elucidation of the Chirality Transfer Mechanism of the Enantioselective Suzuki–Miyaura Cross-Coupling Reaction." Journal of Chemistry 2017 (2017): 1–12. http://dx.doi.org/10.1155/2017/3617527.

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The DFT calculations of the simplified model of the asymmetric Suzuki–Miyaura coupling reaction were performed at the M062x/LANL2DZ theory level at first. It was found that enantioselective reactions mediated by the palladium complexes of chiral C,P-ligands follow a four-stage mechanism similar to that proposed previously as one of the most credible mechanisms. It should be underlined that the presence of substituents in the substrates and the chiral ligand at ortho positions determines the energies of possible diastereoisomeric transition states and intermediates in initial reaction steps. This suggests that, in practice, a sharp selection of theoretically possible paths of chirality transfer from the catalyst to the product should have a place and, therefore, the absolute configuration of the formed atropisomeric product is defined and can be predicted.

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46

Kraft, Jochen, Martin Golkowski, and Thomas Ziegler. "Spiro-fused carbohydrate oxazoline ligands: Synthesis and application as enantio-discrimination agents in asymmetric allylic alkylation." Beilstein Journal of Organic Chemistry 12 (January 29, 2016): 166–71. http://dx.doi.org/10.3762/bjoc.12.18.

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In the present work, we describe a convenient synthesis of spiro-fused D-fructo- and D-psico-configurated oxazoline ligands and their application in asymmetric catalysis. The ligands were synthesized from readily available 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose and 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-psicopyranose, respectively. The latter compounds were partially deprotected under acidic conditions followed by condensation with thiocyanic acid to give an anomeric mixture of the corresponding 1,3-oxazolidine-2-thiones. The anomeric 1,3-oxazolidine-2-thiones were separated after successive benzylation, fully characterized and subjected to palladium catalyzed Suzuki–Miyaura coupling with 2-pyridineboronic acid N-phenyldiethanolamine ester to give the corresponding 2-pyridyl spiro-oxazoline (PyOx) ligands. The spiro-oxazoline ligands showed high asymmetric induction (up to 93% ee) when applied as chiral ligands in palladium-catalyzed allylic alkylation of 1,3-diphenylallyl acetate with dimethyl malonate. The D-fructo-PyOx ligand provided mainly the (R)-enantiomer while the D-psico-configurated ligand gave the (S)-enantiomer with a lower enantiomeric excess.

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47

Mota González, M. L., A. Carrillo Castillo, R. C. Ambrosio Lázaro, J. Flores Méndez, Mario Moreno, Priscy A. Luque, and Dámaso Navarro. "Synthesis and Study of Chemical, Thermal, Mesomorphic, and Optical Properties of Terphenyls Modified with Nitrile Groups." Journal of Chemistry 2017 (2017): 1–9. http://dx.doi.org/10.1155/2017/8275489.

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Abstract:

We report the synthesis, characterization, and the thermotropic and photoluminescence properties of dialkoxyterphenyls with (T12-CN and T12-2CN) and without (T12) nitrile groups. These terphenyls were prepared through the Suzuki-Miyaura cross-coupling reaction using a palladium-based catalyst. The products obtained were analyzed as powders or after being drop-casted or spin-coated on glass. Nuclear Magnetic Resonance (1H NMR) and Fourier Transform Infrared (FTIR) spectroscopy techniques confirmed the structure and purity of the synthesized terphenyls. The mesomorphic behavior was studied by differential scanning calorimetry (DSC), polarizing optical microscopy (POM), and X-ray diffraction (XRD). T12 developed various mesophases, whereas T12-CN and T12-2CN displayed one single mesophase of low order over a wide temperature range. The films topology was studied by AFM and the optical properties were determined by ultraviolet-visible (UV-Vis) spectroscopy and spectrofluorometry. Higher roughness was found for the films prepared with the asymmetric terphenyl (T12-CN). The photoluminescence (PL) spectrum obtained for the asymmetric terphenyl (T12-CN) exhibited the expected characteristics with an emission band centered at 381 nm and an overtone around 760 nm.

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Yajima, Arata, Ayumi Yamaguchi, Fumihiro Saitou, Tomoo Nukada, and Goro Yabuta. "Asymmetric synthesis of abietane diterpenoids via B-alkyl Suzuki–Miyaura coupling. Formal total asymmetric synthesis of 12-deoxyroyleanone and cryptoquinone." Tetrahedron 63, no. 5 (January 2007): 1080–84. http://dx.doi.org/10.1016/j.tet.2006.11.072.

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Yang, Xintong, Guangqing Xu, and Wenjun Tang. "Efficient synthesis of chiral biaryls via asymmetric Suzuki-Miyaura cross-coupling of ortho-bromo aryl triflates." Tetrahedron 72, no. 34 (August 2016): 5178–83. http://dx.doi.org/10.1016/j.tet.2015.12.051.

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Ji, Wangqin, Hai-Hong Wu, and Junliang Zhang. "Axially Chiral Biaryl Monophosphine Oxides Enabled by Palladium/WJ-Phos-Catalyzed Asymmetric Suzuki–Miyaura Cross-coupling." ACS Catalysis 10, no. 2 (January 3, 2020): 1548–54. http://dx.doi.org/10.1021/acscatal.9b04354.

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