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Journal articles on the topic 'C-H silylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Wang, Hong, Guanghui Wang, and Pengfei Li. "Iridium-catalyzed intermolecular directed dehydrogenative ortho C–H silylation." Organic Chemistry Frontiers 4, no. 10 (2017): 1943–46. http://dx.doi.org/10.1039/c7qo00340d.

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2

Zhang, Yanghui, Bo Zhou, and Ailan Lu. "Pd-Catalyzed C–H Silylation Reactions with Disilanes." Synlett 30, no. 06 (2018): 685–93. http://dx.doi.org/10.1055/s-0037-1610339.

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Pd-catalyzed C–H silylation reactions remain underdeveloped. General strategies usually rely on the use of complex bidentate directing groups. C,C-Palladacycles exhibit extremely high reactivity towards hexamethyldisilane and can be disilylated very efficiently. The C,C-palladacycles are prepared through halide-directed C–H activation. This account introduces Pd-catalyzed C–H silylation reactions with disilanes as the silyl source, and is focused on studies on the silylation of C,C-palladacycles.1 Introduction and Background2 Allylic C–H Silylation Reaction3 Coordinating-Ligand-Directed C–H S

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3

Liu, Shun, Qiao Lin, Chunshu Liao, et al. "Ruthenium(ii)/acetate catalyzed intermolecular dehydrogenative ortho C–H silylation of 2-aryl N-containing heterocycles." Organic & Biomolecular Chemistry 17, no. 16 (2019): 4115–20. http://dx.doi.org/10.1039/c9ob00609e.

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The application of a RuHCl(CO)(PPh<sub>3</sub>)<sub>3</sub>–OAc catalytic system for the selective intermolecular mono C–H silylation of 2-aryl heterocycles using HSiEt<sub>3</sub> as the silylating reagent is described for the first time.

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4

Miyake, Yoshihiro, Shuhei Akahori, Tetsuaki Fujihara, Yasushi Tsuji, and Hiroshi Shinokubo. "Synthesis of Tetrasilatetrathia[8]circulenes through C–I and C–H Silylation." Synthesis 53, no. 17 (2021): 2995–3000. http://dx.doi.org/10.1055/a-1437-9917.

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AbstractWe have succeeded in the synthesis of various tetrasilatetrathia[8]circulenes with alkyl and aryl groups on the silicon atoms. We also disclosed the effect of phosphine ligands on palladium-catalyzed silylation of tetraiodotetrathienylene and rhodium-catalyzed intramolecular silylation of tetrasilyltetrathienylenes. Experimental and theoretical analysis revealed the effect of the substituents on the silicon atoms on their electronic property.

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5

Richter, Sven C., and Martin Oestreich. "Emerging Strategies for C–H Silylation." Trends in Chemistry 2, no. 1 (2020): 13–27. http://dx.doi.org/10.1016/j.trechm.2019.07.003.

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6

Huang, Zheng, Huaquan Fang, Qiaoxing He, and Guixia Liu. "Pincer Ruthenium Catalyzed Intramolecular Silylation of C(sp2)–H Bonds." Synlett 28, no. 18 (2017): 2468–72. http://dx.doi.org/10.1055/s-0036-1590982.

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Reported herein is a highly efficient intramolecular silylation of aromatic C–H bonds catalyzed by a pincer ruthenium complex, giving benzoxasiloles under relatively mild reaction conditions with broad substrate scope and low catalyst loadings. The silylation product can be further converted into a biaryl product by Pd-catalyzed Hiyama–Denmark cross-coupling reactions.

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7

Bähr, Susanne, and Martin Oestreich. "The electrophilic aromatic substitution approach to C–H silylation and C–H borylation." Pure and Applied Chemistry 90, no. 4 (2018): 723–31. http://dx.doi.org/10.1515/pac-2017-0902.

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AbstractSeveral approaches toward electrophilic C–H silylation of electron-rich arenes are discussed, comprising transition-metal-catalyzed processes as well as Lewis-acid- and Brønsted-acid-induced protocols. These methods differ in the catalytic generation of the silicon electrophile but share proton removal in form of dihydrogen. With slight modifications, these methods are often also applicable to the related electrophilic C–H borylation.

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8

Cheng, Chen, and John F. Hartwig. "Catalytic Silylation of Unactivated C–H Bonds." Chemical Reviews 115, no. 17 (2015): 8946–75. http://dx.doi.org/10.1021/cr5006414.

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9

Larsson, Johanna M., Tony S. N. Zhao, and Kálmán J. Szabó. "Palladium-Catalyzed Oxidative Allylic C−H Silylation." Organic Letters 13, no. 7 (2011): 1888–91. http://dx.doi.org/10.1021/ol200445b.

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10

Liu, Shihui, Peng Pan, Huaqiang Fan, Hao Li, Wei Wang, and Yongqiang Zhang. "Photocatalytic C–H silylation of heteroarenes by using trialkylhydrosilanes." Chemical Science 10, no. 13 (2019): 3817–25. http://dx.doi.org/10.1039/c9sc00046a.

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11

Hartwig, John F., and Erik A. Romero. "Iridium-catalyzed silylation of unactivated C–H bonds." Tetrahedron 75, no. 31 (2019): 4059–70. http://dx.doi.org/10.1016/j.tet.2019.05.055.

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12

Yurino, Taiga. "Undirected Dehydrogenative Silylation of Aromatic C-H Bond." Journal of Synthetic Organic Chemistry, Japan 75, no. 1 (2017): 64–65. http://dx.doi.org/10.5059/yukigoseikyokaishi.75.64.

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13

Cheng, Chen, and John F. Hartwig. "Iridium-Catalyzed Silylation of Aryl C–H Bonds." Journal of the American Chemical Society 137, no. 2 (2015): 592–95. http://dx.doi.org/10.1021/ja511352u.

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14

Zhang, Qing-Wei, Kun An, Li-Chuan Liu, et al. "Rhodium-Catalyzed Intramolecular C−H Silylation by Silacyclobutanes." Angewandte Chemie International Edition 55, no. 21 (2016): 6319–23. http://dx.doi.org/10.1002/anie.201602376.

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15

Zhang, Qing-Wei, Kun An, Li-Chuan Liu, et al. "Rhodium-Catalyzed Intramolecular C−H Silylation by Silacyclobutanes." Angewandte Chemie 128, no. 21 (2016): 6427–31. http://dx.doi.org/10.1002/ange.201602376.

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16

Oyamada, Juzo, Masayoshi Nishiura, and Zhaomin Hou. "Scandium-Catalyzed Silylation of Aromatic CH Bonds." Angewandte Chemie 123, no. 45 (2011): 10908–11. http://dx.doi.org/10.1002/ange.201105636.

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17

Oyamada, Juzo, Masayoshi Nishiura, and Zhaomin Hou. "Scandium-Catalyzed Silylation of Aromatic CH Bonds." Angewandte Chemie International Edition 50, no. 45 (2011): 10720–23. http://dx.doi.org/10.1002/anie.201105636.

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18

Knochel, Paul, and Nadja Barl. "Scandium-Catalyzed Silylation of Aromatic C–H Bonds." Synfacts 8, no. 01 (2011): 0083. http://dx.doi.org/10.1055/s-0031-1289468.

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19

Toutov, Anton A., Wen-Bo Liu, Kerry N. Betz, Brian M. Stoltz, and Robert H. Grubbs. "Catalytic C–H bond silylation of aromatic heterocycles." Nature Protocols 10, no. 12 (2015): 1897–903. http://dx.doi.org/10.1038/nprot.2015.118.

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20

Devaraj, K., C. Sollert, C. Juds, P. J. Gates, and L. T. Pilarski. "Ru-catalysed C–H silylation of unprotected gramines, tryptamines and their congeners." Chemical Communications 52, no. 34 (2016): 5868–71. http://dx.doi.org/10.1039/c6cc00803h.

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21

Liu, Pei, Na Hao, Dong Yang, et al. "Iron-catalyzed para-selective C–H silylation of benzamide derivatives with chlorosilanes." Organic Chemistry Frontiers 8, no. 11 (2021): 2442–48. http://dx.doi.org/10.1039/d1qo00243k.

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22

Xu, Wengang, Jie Hui Pek, and Naohiko Yoshikai. "Iron-Catalyzed Directed C−H Silylation of Pivalophenone N−H Imines." Asian Journal of Organic Chemistry 7, no. 7 (2018): 1351–54. http://dx.doi.org/10.1002/ajoc.201800171.

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23

Lee, Taegyo, and John F. Hartwig. "Rhodium-Catalyzed Enantioselective Silylation of Cyclopropyl C−H Bonds." Angewandte Chemie 128, no. 30 (2016): 8865–69. http://dx.doi.org/10.1002/ange.201603153.

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24

Toutov, Anton A., Kerry N. Betz, David P. Schuman, et al. "Alkali Metal-Hydroxide-Catalyzed C(sp)–H Bond silylation." Journal of the American Chemical Society 139, no. 4 (2017): 1668–74. http://dx.doi.org/10.1021/jacs.6b12114.

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25

Lee, Taegyo, and John F. Hartwig. "Rhodium-Catalyzed Enantioselective Silylation of Cyclopropyl C−H Bonds." Angewandte Chemie International Edition 55, no. 30 (2016): 8723–27. http://dx.doi.org/10.1002/anie.201603153.

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26

Lu, Biao, and John R Falck. "Efficient Iridium-Catalyzed CH Functionalization/Silylation of Heteroarenes." Angewandte Chemie 120, no. 39 (2008): 7618–20. http://dx.doi.org/10.1002/ange.200802456.

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27

Lu, Biao, and John R Falck. "Efficient Iridium-Catalyzed CH Functionalization/Silylation of Heteroarenes." Angewandte Chemie International Edition 47, no. 39 (2008): 7508–10. http://dx.doi.org/10.1002/anie.200802456.

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28

Ma, Yuanhong, Baoli Wang, Liang Zhang, and Zhaomin Hou. "Boron-Catalyzed Aromatic C–H Bond Silylation with Hydrosilanes." Journal of the American Chemical Society 138, no. 11 (2016): 3663–66. http://dx.doi.org/10.1021/jacs.6b01349.

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29

Ji, Xiaoming, Feng Wei, Bin Wan, Cang Cheng, and Yanghui Zhang. "Palladium-catalyzed intermolecular C–H silylation initiated by aminopalladation." Chemical Communications 56, no. 56 (2020): 7801–4. http://dx.doi.org/10.1039/d0cc00872a.

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30

Cheng, Chen, and John F. Hartwig. "ChemInform Abstract: Catalytic Silylation of Unactivated C-H Bonds." ChemInform 46, no. 45 (2015): no. http://dx.doi.org/10.1002/chin.201545254.

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31

Larsson, Johanna M., Tony S. N. Zhao, and Kalman J. Szabo. "ChemInform Abstract: Palladium-Catalyzed Oxidative Allylic C-H Silylation." ChemInform 42, no. 27 (2011): no. http://dx.doi.org/10.1002/chin.201127186.

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32

Pan, Jin-Long, Quan-Zhe Li, Ting-Yu Zhang, Si-Hua Hou, Jun-Cheng Kang, and Shu-Yu Zhang. "Palladium-catalyzed direct intermolecular silylation of remote unactivated C(sp3)–H bonds." Chemical Communications 52, no. 89 (2016): 13151–54. http://dx.doi.org/10.1039/c6cc07885k.

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An efficient and convenient method has been developed to achieve direct silylation of unactivated remote primary or secondary C(sp<sup>3</sup>)–H bonds to form C–Si bonds with hexamethyldisilane (HMDS).

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33

Areerob, Thanita, Nurak Grisdanurak, and Siriluk Chiarakorn. "Improvement of BTEX Adsorption Using Silylated RH-MCM-41 Synthesized from Rice Husk Silica." Materials Science Forum 700 (September 2011): 231–35. http://dx.doi.org/10.4028/www.scientific.net/msf.700.231.

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RH-MCM-41, a mesoporous molecular sieve, was successfully synthesized from silica extracted from rice husk. The presence of silanol functional group (Si-OH) on its surface causes adverse effects on the adsorption of some non-polar compounds, especially benzene, toluene, ethylbenzene and xylene (BTEX). Thus, this work aims to enhance the adsorbability of RH-MCM-41 on BTEX adsorption by in-situ and ex-situ silylation. Trimethylchlorosilane (TMCS) was used as a silylating reagent to reduce silanol groups. The ex-situ silylation was carried out by adding as-synthesized RH-MCM-41 into 5% v/v of TMC

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34

Liu, Pei, Na Hao, Dong Yang, et al. "Correction: Iron-catalyzed para-selective C–H silylation of benzamide derivatives with chlorosilanes." Organic Chemistry Frontiers 8, no. 11 (2021): 2863. http://dx.doi.org/10.1039/d1qo90032c.

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35

Li, Bin, and Pierre H. Dixneuf. "Metal-catalyzed silylation of sp3C–H bonds." Chemical Society Reviews 50, no. 8 (2021): 5062–85. http://dx.doi.org/10.1039/d0cs01392g.

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Metal-catalyzed activations of inert sp<sup>3</sup>C–H bonds have recently brought a revolution in the synthesis of useful molecules and molecular materials, due to the interest of the formed sp<sup>3</sup>C–SiR<sub>3</sub> silanes, stable organometallic species, and for further functionalizations that sp<sup>3</sup>C–H bonds cannot reach directly.

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36

Chen, Jian-Chih, Chih-Hua Chen, Kai-Chi Chang, et al. "Evaluation of the Grafting Efficacy of Active Biomolecules of Phosphatidylcholine and Type I Collagen on Polyether Ether Ketone: In Vitro and In Vivo." Polymers 13, no. 13 (2021): 2081. http://dx.doi.org/10.3390/polym13132081.

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Biomolecule grafting on polyether ether ketone (PEEK) was used to improve cell affinity caused by surface inertness. This study demonstrated the sequence-polished (P) and sulfonated (SA) PEEK modification to make a 3D structure, active biomolecule graftings through PEEK silylation (SA/SI) and then processed with phosphatidylcholine (with silylation of SA/SI/PC; without SA/PC) and type I collagen (COL I, with silylation of SA/SI/C; without SA/C). Different modified PEEKs were implanted for 4, 8, and 12 weeks for histology. Sulfonated PEEK of SA showed the surface roughness was significantly inc

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37

Hartwig, John F. "Borylation and Silylation of C–H Bonds: A Platform for Diverse C–H Bond Functionalizations." Accounts of Chemical Research 45, no. 6 (2011): 864–73. http://dx.doi.org/10.1021/ar200206a.

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38

Zhang, Ming, Shan Gao, Juan Tang, et al. "Asymmetric synthesis of chiral organosilicon compounds via transition metal-catalyzed stereoselective C–H activation and silylation." Chemical Communications 57, no. 67 (2021): 8250–63. http://dx.doi.org/10.1039/d1cc02839a.

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39

Murata, Miki, and Yuna Maeda. "Ruthenium-Catalyzed Functional-Group-Directed C-H Silylation and Borylation." Journal of Synthetic Organic Chemistry, Japan 77, no. 9 (2019): 876–82. http://dx.doi.org/10.5059/yukigoseikyokaishi.77.876.

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40

Su, Bo, and John F. Hartwig. "Ir-Catalyzed Enantioselective, Intramolecular Silylation of Methyl C–H Bonds." Journal of the American Chemical Society 139, no. 35 (2017): 12137–40. http://dx.doi.org/10.1021/jacs.7b06679.

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41

Minami, Yasunori, Takeshi Komiyama, and Tamejiro Hiyama. "Straightforward Synthesis of HOMSi Reagents via sp2 C–H Silylation." Chemistry Letters 44, no. 8 (2015): 1065–67. http://dx.doi.org/10.1246/cl.150359.

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42

Oyamada, Juzo, Masayoshi Nishiura, and Zhaomin Hou. "ChemInform Abstract: Scandium-Catalyzed Silylation of Aromatic C-H Bonds." ChemInform 43, no. 13 (2012): no. http://dx.doi.org/10.1002/chin.201213200.

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43

Kuninobu, Yoichiro, Takahiro Nakahara, Hirotaka Takeshima, and Kazuhiko Takai. "Rhodium-Catalyzed Intramolecular Silylation of Unactivated C(sp3)–H Bonds." Organic Letters 15, no. 2 (2013): 426–28. http://dx.doi.org/10.1021/ol303353m.

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44

Cheng, Chen, and John F. Hartwig. "ChemInform Abstract: Iridium-Catalyzed Silylation of Aryl C-H Bonds." ChemInform 46, no. 27 (2015): no. http://dx.doi.org/10.1002/chin.201527237.

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45

He, Tao, Bin Li, Lichuan Liu, Wenpeng Ma, and Wei He. "Rhodium‐Catalyzed Intermolecular Silylation of C sp −H by Silacyclobutanes." Chemistry – A European Journal 27, no. 18 (2021): 5648–52. http://dx.doi.org/10.1002/chem.202100084.

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46

Du, Pan, and Jiyang Zhao. "Comparative DFT study of metal-free Lewis acid-catalyzed C–H and N–H silylation of (hetero)arenes: mechanistic studies and expansion of catalyst and substrate scope." RSC Advances 9, no. 64 (2019): 37675–85. http://dx.doi.org/10.1039/c9ra07985h.

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47

Rubio-Pérez, Laura, Manuel Iglesias, Julen Munárriz, et al. "A well-defined NHC–Ir(iii) catalyst for the silylation of aromatic C–H bonds: substrate survey and mechanistic insights." Chemical Science 8, no. 7 (2017): 4811–22. http://dx.doi.org/10.1039/c6sc04899d.

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48

Yan, Zhi-Bo, Meng Peng, Qi-Long Chen, et al. "An effective and versatile strategy for the synthesis of structurally diverse heteroarylsilanes via Ir(iii)-catalyzed C–H silylation." Chemical Science 12, no. 28 (2021): 9748–53. http://dx.doi.org/10.1039/d1sc02344f.

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49

Huang, Hongtai, Tao Li, Jiazhuang Wang, Guiping Qin, and Tiebo Xiao. "Recent Advance in Transition-Metal-Catalyzed Silylation of C-H Bonds." Chinese Journal of Organic Chemistry 39, no. 6 (2019): 1511. http://dx.doi.org/10.6023/cjoc201903078.

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50

Li, Wei, Xiaolei Huang, and Jingsong You. "Ruthenium-Catalyzed Intermolecular Direct Silylation of Unreactive C(sp3)–H Bonds." Organic Letters 18, no. 4 (2016): 666–68. http://dx.doi.org/10.1021/acs.orglett.5b03593.

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