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Journal articles on the topic 'C-H Amination'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Zhao, Yingsheng, Chao Wang, and Jian Han. "Recent Development in N-Auxilixary-Assisted Intramolecular Amination for Amine Substrates." Synlett 26, no. 08 (2015): 997–1002. http://dx.doi.org/10.1055/s-0034-1380167.

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Direct coupling of N–H with C–H has aroused great attention in the last decades; during which the directing-group-assisted intramolecular C–N bond formation via transition metal has been achieved significant progress. Herein, we highlight the recent development in the directing-group-assisted intramolecular amination for amine substrates to build the important N-containing heterocyclic compounds.1 Introduction2 Triflamide-Promoted Intramolecular Amination3 Picolinamide-Assisted Intramolecular Amination4 Palladium-Catalyzed Intramolecular Amination under Assistance of Oxalyl Amide5 Conclusion

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2

Yeston, Jake. "Double C–H amination." Science 371, no. 6529 (2021): 580.4–580. http://dx.doi.org/10.1126/science.371.6529.580-d.

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3

Xu, Fen, Yuan-Yuan Song, Wen-Jing Zhu, Chun-Sen Liu, Ya-Zhou Lu, and Miao Du. "Rhodium-catalyzed multiple C–H activation/highly meta-selective C–H amination between amidines and alkynes." Chemical Communications 56, no. 76 (2020): 11227–30. http://dx.doi.org/10.1039/d0cc04885b.

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4

Bandara, H. M. D., D. Jin, M. A. Mantell, et al. "Non-directed aromatic C–H amination: catalytic and mechanistic studies enabled by Pd catalyst and reagent design." Catalysis Science & Technology 6, no. 14 (2016): 5304–10. http://dx.doi.org/10.1039/c6cy00457a.

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5

Louillat, Marie-Laure, and Frederic W. Patureau. "Oxidative C–H amination reactions." Chem. Soc. Rev. 43, no. 3 (2014): 901–10. http://dx.doi.org/10.1039/c3cs60318k.

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6

Singh, Ritesh, and Anirban Mukherjee. "Metalloporphyrin Catalyzed C–H Amination." ACS Catalysis 9, no. 4 (2019): 3604–17. http://dx.doi.org/10.1021/acscatal.9b00009.

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7

Jeffrey, Jenna L., and Richmond Sarpong. "Intramolecular C(sp3)–H amination." Chemical Science 4, no. 11 (2013): 4092. http://dx.doi.org/10.1039/c3sc51420j.

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8

Bach, T., A. Nörder, P. Herrmann, and E. Herdtweck. "Diastereoselective Catalytic C-H Amination." Synfacts 2010, no. 10 (2010): 1141. http://dx.doi.org/10.1055/s-0030-1258647.

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9

Zhang, Lei, Laurent Liardet, Jingshan Luo, Dan Ren, Michael Grätzel, and Xile Hu. "Photoelectrocatalytic arene C–H amination." Nature Catalysis 2, no. 4 (2019): 366–73. http://dx.doi.org/10.1038/s41929-019-0231-9.

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10

Wang, Juping, Kangcheng Zheng, Ting Li, and Xiaojing Zhan. "Mechanism and Chemoselectivity of Mn-Catalyzed Intramolecular Nitrene Transfer Reaction: C–H Amination vs. C=C Aziridination." Catalysts 10, no. 3 (2020): 292. http://dx.doi.org/10.3390/catal10030292.

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The reactivity, mechanism and chemoselectivity of the Mn-catalyzed intramolecular C–H amination versus C=C aziridination of allylic substrate cis-4-hexenylsulfamate are investigated by BP86 density functional theory computations. Emphasis is placed on the origins of high reactivity and high chemoselectivity of Mn catalysis. The N p orbital character of frontier orbitals, a strong electron-withdrawing porphyrazine ligand and a poor π backbonding of high-valent MnIII metal to N atom lead to high electrophilic reactivity of Mn-nitrene. The calculated energy barrier of C–H amination is 9.9 kcal/mo

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11

D'Amato, Erica M., Jonas Börgel, and Tobias Ritter. "Aromatic C–H amination in hexafluoroisopropanol." Chemical Science 10, no. 8 (2019): 2424–28. http://dx.doi.org/10.1039/c8sc04966a.

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12

Hilinski, Michael, Shea Johnson, and Logan Combee. "Organocatalytic Atom-Transfer C(sp3)–H Oxidation." Synlett 29, no. 18 (2018): 2331–36. http://dx.doi.org/10.1055/s-0037-1610432.

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Predictably site-selective catalytic methods for intermolecular C(sp3)–H hydroxylation and amination hold great promise for the synthesis and late-stage modification of complex molecules. Transition-metal catalysis has been the most common approach for early investigations of this type of reaction. In comparison, there are far fewer reports of organocatalytic methods for direct oxygen or nitrogen insertion into C–H bonds. Herein, we provide an overview of early efforts in this area, with particular emphasis on our own recent development of an iminium salt that catalyzes both oxygen and nitrog

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13

Sabat, Nazarii, Martin Klečka, Lenka Slavětínská, Blanka Klepetářová, and Michal Hocek. "Direct C–H amination and C–H chloroamination of 7-deazapurines." RSC Adv. 4, no. 107 (2014): 62140–43. http://dx.doi.org/10.1039/c4ra13143f.

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14

Jin, Li-Mei, Pan Xu, Jingjing Xie, and X. Peter Zhang. "Enantioselective Intermolecular Radical C–H Amination." Journal of the American Chemical Society 142, no. 49 (2020): 20828–36. http://dx.doi.org/10.1021/jacs.0c10415.

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15

Barman, Dipti N., and Kenneth M. Nicholas. "Copper-Catalyzed Intramolecular C-H Amination." European Journal of Organic Chemistry 2011, no. 5 (2010): 908–11. http://dx.doi.org/10.1002/ejoc.201001160.

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16

Boudet, Nadege, and Simon B. Blakey. "ChemInform Abstract: Enantioselective C-H Amination." ChemInform 42, no. 45 (2011): no. http://dx.doi.org/10.1002/chin.201145231.

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17

Lebel, Hélène, Carl Trudel, and Cédric Spitz. "Stereoselective intermolecular C–H amination reactions." Chemical Communications 48, no. 63 (2012): 7799. http://dx.doi.org/10.1039/c2cc33689h.

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18

Sun, Chunrui, Jingwei Li, Daesung Lee, Genping Huang, and Yuanzhi Xia. "Formal C–H amination of cyclopropenes." Chemical Communications 48, no. 89 (2012): 10990. http://dx.doi.org/10.1039/c2cc35329f.

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19

Gephart, Raymond T., and Timothy H. Warren. "Copper-Catalyzed sp3 C–H Amination." Organometallics 31, no. 22 (2012): 7728–52. http://dx.doi.org/10.1021/om300840z.

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20

Yu, Yang, Gen Luo, Jimin Yang, and Yi Luo. "Cobalt-catalysed unactivated C(sp3)–H amination: two-state reactivity and multi-reference electronic character." Catalysis Science & Technology 9, no. 8 (2019): 1879–90. http://dx.doi.org/10.1039/c9cy00239a.

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A remarkable two-state reactivity scenario and an unusual multi-reference character have been computationally found in Co-catalysed C(sp<sup>3</sup>)–H amination. In addition, the investigation on the additive, aminating reagent, metal center, and auxiliary ligand provides implications for development of new catalytic C–H functionalization systems.

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21

Scamp, Ryan J., Jared W. Rigoli, and Jennifer M. Schomaker. "Chemoselective silver-catalyzed nitrene insertion reactions." Pure and Applied Chemistry 86, no. 3 (2014): 381–93. http://dx.doi.org/10.1515/pac-2014-5040.

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AbstractA review of recent developments in silver(I)-catalyzed nitrene insertions into olefin and C–H bonds is presented, with a particular emphasis on reactions where the chemoselectivity can be tuned to promote either aziridination or C–H amination. The scope and synthetic utility of various silver catalysts are described, as well as preliminary investigations into the mechanisms of silver-catalyzed aminations.

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22

Li, Xiaobin, Chengxi Zhang, Chenchen Wang, et al. "Modular synthesis of (C-10 to C-13)-substituted-9,14-diaryl-9,14-dihydrodibenzo[a,c]phenazines via a subsequent Buchwald–Hartwig amination and C–H amination strategy." Chemical Communications 56, no. 15 (2020): 2260–63. http://dx.doi.org/10.1039/c9cc09997b.

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23

Collet, Florence, Camille Lescot, Chungen Liang, and Philippe Dauban. "Studies in catalytic C–H amination involving nitrene C–H insertion." Dalton Transactions 39, no. 43 (2010): 10401. http://dx.doi.org/10.1039/c0dt00283f.

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24

Kantak, Abhishek A., Louis Marchetti, and Brenton DeBoef. "Regioselective C–H bond amination by aminoiodanes." Chemical Communications 51, no. 17 (2015): 3574–77. http://dx.doi.org/10.1039/c4cc10246k.

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A new approach for the direct amination of 2-phenylpyridine derivatives using a diphthalimide-iodane and copper triflate has been developed. A series of different 2-phenylpyridine derivatives were aminated with yields up to 88%. Mechanistic investigations indicate that the reaction proceeds via a copper-mediated single electron transfer.

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25

Lapuh, María Ivana, Alejandro Dana, Pablo H. Di Chenna, Benjamin Darses, Fernando J. Durán, and Philippe Dauban. "Late-stage C–H amination of abietane diterpenoids." Organic & Biomolecular Chemistry 17, no. 19 (2019): 4736–46. http://dx.doi.org/10.1039/c9ob00272c.

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26

Hou, Zhong-Wei, Laiqiang Li, and Lei Wang. "Organocatalytic electrochemical amination of benzylic C–H bonds." Organic Chemistry Frontiers 8, no. 17 (2021): 4700–4705. http://dx.doi.org/10.1039/d1qo00746g.

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27

Li, Zhen, Yan Ding, and Jin Liu. "Study on Primary Reaction Kinetics of Melamine Aminated Monomethoxylpoly (ethylene Glycol)." Advanced Materials Research 450-451 (January 2012): 374–78. http://dx.doi.org/10.4028/www.scientific.net/amr.450-451.374.

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The reaction kinetics of amination of monomethoxylpoly (ethylene glycol) (mPEG) with melamine (MA) at the molar ratio of 1:1 was studied by FTIR. This amination reaction was carried out with potassium hydroxide as reaction catalyst under high-pressure conditions at different temperature (160 °C, 170 °C, 180 °C, and 190°C) for different time (2 h, 3 h, 4 h, 5 h and 6 h). A series of melamine aminated monomethoxylpoly (ethylene glycol) (MA-mPEG) were synthesized, and the long chain of polyethylene glycol ether was grafted on the amino groups of melamine by amination. The amination kinetics param

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28

Sun, Yiming, Qifeng Ding, Yang Yu, Yide He, and Fei Huang. "Progress in Co-Catalyzed C-H Amination." Chinese Journal of Organic Chemistry 39, no. 12 (2019): 3363. http://dx.doi.org/10.6023/cjoc201906026.

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29

See, Yi Yang, and Melanie S. Sanford. "C–H Amination of Arenes with Hydroxylamine." Organic Letters 22, no. 8 (2020): 2931–34. http://dx.doi.org/10.1021/acs.orglett.0c00598.

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30

Wang, Peng, Gen-Cheng Li, Pankaj Jain, et al. "Ligand-Promotedmeta-C–H Amination and Alkynylation." Journal of the American Chemical Society 138, no. 42 (2016): 14092–99. http://dx.doi.org/10.1021/jacs.6b08942.

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31

Collet, Florence, Camille Lescot, and Philippe Dauban. "Catalytic C–H amination: the stereoselectivity issue." Chemical Society Reviews 40, no. 4 (2011): 1926. http://dx.doi.org/10.1039/c0cs00095g.

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32

Kohmura, Yoshinori, and Tsutomu Katsuki. "Mn(salen)-catalyzed enantioselective CH amination." Tetrahedron Letters 42, no. 19 (2001): 3339–42. http://dx.doi.org/10.1016/s0040-4039(01)00427-0.

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33

Juliá, Fabio, Alessandro Ruffoni, and Daniele Leonori. "Aromatic C–H Amination Using Alkyl Amines." Trends in Chemistry 2, no. 5 (2020): 480–81. http://dx.doi.org/10.1016/j.trechm.2020.01.005.

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34

Müller, P., R. Dodd, P. Dauban, C. Liang, F. Robert-Peillard, and C. Fruit. "Rhodium-Catalyzed Diastereoselective Intermolecular C-H Amination." Synfacts 2006, no. 9 (2006): 0912. http://dx.doi.org/10.1055/s-2006-942060.

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35

Alt, Isabel T., and Bernd Plietker. "Iron-Catalyzed Intramolecular C(sp2 )−H Amination." Angewandte Chemie International Edition 55, no. 4 (2015): 1519–22. http://dx.doi.org/10.1002/anie.201510045.

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36

Jeffrey, Jenna L., and Richmond Sarpong. "ChemInform Abstract: Intramolecular C(sp3)-H Amination." ChemInform 45, no. 1 (2013): no. http://dx.doi.org/10.1002/chin.201401254.

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37

Louillat, Marie-Laure, and Frederic W. Patureau. "ChemInform Abstract: Oxidative C-H Amination Reactions." ChemInform 45, no. 17 (2014): no. http://dx.doi.org/10.1002/chin.201417273.

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38

Gephart, Raymond T., Daria L. Huang, Mae Joanne B. Aguila, Graham Schmidt, Andi Shahu, and Timothy H. Warren. "Catalytic CH Amination with Aromatic Amines." Angewandte Chemie 124, no. 26 (2012): 6594–98. http://dx.doi.org/10.1002/ange.201201921.

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39

Gephart, Raymond T., Daria L. Huang, Mae Joanne B. Aguila, Graham Schmidt, Andi Shahu, and Timothy H. Warren. "Catalytic CH Amination with Aromatic Amines." Angewandte Chemie International Edition 51, no. 26 (2012): 6488–92. http://dx.doi.org/10.1002/anie.201201921.

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40

Paradine, Shauna M., and M. Christina White. "Iron-Catalyzed Intramolecular Allylic C–H Amination." Journal of the American Chemical Society 134, no. 4 (2012): 2036–39. http://dx.doi.org/10.1021/ja211600g.

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41

Völler, Jan-Stefan. "Primary amination of C(sp3)–H bonds." Nature Catalysis 3, no. 6 (2020): 473. http://dx.doi.org/10.1038/s41929-020-0477-2.

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42

Puthanveedu, Mahesh, Vladislav Khamraev, Lukas Brieger, Carsten Strohmann, and Andrey P. Antonchick. "Electrochemical Dehydrogenative C(sp 2 )−H Amination." Chemistry – A European Journal 27, no. 30 (2021): 8008–12. http://dx.doi.org/10.1002/chem.202100960.

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43

Evoniuk, Christopher J., Sean P. Hill, Kenneth Hanson, and Igor V. Alabugin. "Double C–H amination by consecutive SET oxidations." Chemical Communications 52, no. 44 (2016): 7138–41. http://dx.doi.org/10.1039/c6cc03106d.

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44

Zhu, Xu, and Shunsuke Chiba. "TEMPO-mediated allylic C–H amination with hydrazones." Org. Biomol. Chem. 12, no. 26 (2014): 4567–70. http://dx.doi.org/10.1039/c4ob00839a.

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TEMPO-mediated reactions of alkenyl hydrazones afforded azaheterocycles via sp<sup>3</sup> C–H allylic amination. The transformation is featured by a sequence of remote allylic H-radical shift and allylic homolytic substitution with hydrazone radicals.

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45

Song, Liangliang, Guilong Tian, Johan Van der Eycken, and Erik V. Van der Eycken. "Intramolecular cascade annulation triggered by rhodium(III)-catalyzed sequential C(sp2)–H activation and C(sp3)–H amination." Beilstein Journal of Organic Chemistry 15 (February 27, 2019): 571–76. http://dx.doi.org/10.3762/bjoc.15.52.

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A rhodium(III)-catalyzed intramolecular oxidative annulation of O-substituted N-hydroxyacrylamides for the construction of indolizinones via sequential C(sp2)–H activation and C(sp3)–H amination has been developed. This approach shows excellent functional-group tolerance. The synthesized scaffold forms the core of many natural products with pharmacological relevance.

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46

Shi, Jianxue, Jingjing Li, Wenjing Zhao, et al. "Regioselective intramolecular sp2 C–H amination: direct vs. mediated electrooxidation." Organic Chemistry Frontiers 8, no. 7 (2021): 1581–86. http://dx.doi.org/10.1039/d0qo01584a.

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47

Villanueva, Omar, Nina Mace Weldy, Simon B. Blakey, and Cora E. MacBeth. "Cobalt catalyzed sp3 C–H amination utilizing aryl azides." Chemical Science 6, no. 11 (2015): 6672–75. http://dx.doi.org/10.1039/c5sc01162k.

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A dinuclear Co(ii) complex supported by a modular, tunable redox-active ligand system is capable of selective C–H amination to form indolines from aryl azides in good yields at low (1 mol%) catalyst loading.

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48

Zhang, Xuelin, Ruizhi Guo, and Xiaodan Zhao. "Organoselenium-catalyzed synthesis of indoles through intramolecular C–H amination." Organic Chemistry Frontiers 2, no. 10 (2015): 1334–37. http://dx.doi.org/10.1039/c5qo00179j.

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49

Lang, Kai, Chaoqun Li, Isaac Kim, and X. Peter Zhang. "Enantioconvergent Amination of Racemic Tertiary C–H Bonds." Journal of the American Chemical Society 142, no. 49 (2020): 20902–11. http://dx.doi.org/10.1021/jacs.0c11103.

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50

Paudyal, M. P., A. M. Adebesin, S. R. Burt, et al. "Dirhodium-catalyzed C-H arene amination using hydroxylamines." Science 353, no. 6304 (2016): 1144–47. http://dx.doi.org/10.1126/science.aaf8713.

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