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Journal articles on the topic 'Electrophilic amination'

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1

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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2

Zhou, Zhe, and László Kürti. "Electrophilic Amination: An Update." Synlett 30, no. 13 (2019): 1525–35. http://dx.doi.org/10.1055/s-0037-1611861.

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In this account, we provide an overview of some recent advances in electrophilic amination methodologies that have been developed in the Kürti group over the last seven years. Our group’s focus has been to develop novel amination methodologies that directly yield N-unprotected amine products.1 Introduction2 Amination of Boronic Acids3 Aziridination of Unactivated Olefins4 Rhodium-Catalyzed C–H Amination of Arenes5 Synthesis of Carbazoles6 Amination of Aryl- and Alkylmetals7 Doubly Electrophilic N-Linchpin Reagents8 Aza-Rubottom Oxidation of Silyl Enol Ethers9 Summary
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3

Erdik, Ender, and Mehmet Ay. "Electrophilic amination of carbanions." Chemical Reviews 89, no. 8 (1989): 1947–80. http://dx.doi.org/10.1021/cr00098a014.

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4

Niwa, Yasuki, Kazuki Takayama, and Makoto Shimizu. "Electrophilic amination with iminomalonate." Tetrahedron Letters 42, no. 32 (2001): 5473–76. http://dx.doi.org/10.1016/s0040-4039(01)01022-x.

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5

Rauser, Marian, Christoph Ascheberg, and Meike Niggemann. "Electrophilic Amination with Nitroarenes." Angewandte Chemie International Edition 56, no. 38 (2017): 11570–74. http://dx.doi.org/10.1002/anie.201705356.

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6

Rauser, Marian, Christoph Ascheberg, and Meike Niggemann. "Electrophilic Amination with Nitroarenes." Angewandte Chemie 129, no. 38 (2017): 11728–32. http://dx.doi.org/10.1002/ange.201705356.

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7

Velarde-Ortiz, Raffet, Albert Guijarro, and Reuben D. Rieke. "Electrophilic amination of organozinc halides." Tetrahedron Letters 39, no. 50 (1998): 9157–60. http://dx.doi.org/10.1016/s0040-4039(98)02108-x.

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8

Greck, Christine, and Jean Genêt. "Electrophilic Amination: New Synthetic Applications." Synlett 1997, no. 7 (1997): 741–48. http://dx.doi.org/10.1055/s-1997-5745.

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9

Gouverneur, V., and L. Ghosez. "Electrophilic amination of 2-azadienes." Tetrahedron 52, no. 21 (1996): 7585–98. http://dx.doi.org/10.1016/0040-4020(96)00268-2.

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10

Fukami, Yutaro, Takamasa Wada, Tatsuhiko Meguro, Noritaka Chida, and Takaaki Sato. "Copper-catalyzed electrophilic amination using N-methoxyamines." Organic & Biomolecular Chemistry 14, no. 24 (2016): 5486–89. http://dx.doi.org/10.1039/c5ob02167g.

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11

Li, Gang, Chunqi Jia, Kai Sun, et al. "Copper(ii)-catalyzed electrophilic amination of quinoline N-oxides with O-benzoyl hydroxylamines." Organic & Biomolecular Chemistry 13, no. 11 (2015): 3207–10. http://dx.doi.org/10.1039/c5ob00135h.

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Copper acetate-catalyzed C–H bond functionalization amination of quinoline N-oxides was achieved using O-benzoyl hydroxylamine as an electrophilic amination reagent, thereby affording the desired products in moderate to excellent yields.
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12

Yan, Xiaoyu, Xianghua Yang, and Chanjuan Xi. "Recent progress in copper-catalyzed electrophilic amination." Catal. Sci. Technol. 4, no. 12 (2014): 4169–77. http://dx.doi.org/10.1039/c4cy00773e.

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13

Luan, Xinjun, and Jingxun Yu. "Hydroxylamines as One-Atom Nitrogen Sources for Metal-Catalyzed Cycloadditions." Synthesis 53, no. 08 (2021): 1423–33. http://dx.doi.org/10.1055/s-0040-1706017.

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AbstractTransition-metal-catalyzed C–N bond formation is one of the most important pathways to synthesize N-heterocycles. Hydroxylamines can be transformed into a nucleophilic reagent to react with a carbon cation or coordinate with a transition metal; it can also become an electrophilic nitrogen source to react with arenes, alkenes, and alkynes. In this short review, the progress made on transition-metal-catalyzed cycloadditions with hydroxylamines as a nitrogen source is summarized.1 Introduction2 Cycloaddition To Form Aziridine Derivatives2.1 Intramolecular Cycloaddition To Form Aziridine D
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14

Cao, Hong-wei, Rudolph A. Abramovitch, Joseph M. Beckert, et al. "Electrophilic Amination. Direct Primary Amination of Arenes Using Phthalimide Derivatives." HETEROCYCLES 28, no. 2 (1989): 623. http://dx.doi.org/10.3987/com-88-s86.

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15

Erdik, Ender. "Electrophilic α-amination of carbonyl compounds". Tetrahedron 60, № 40 (2004): 8747–82. http://dx.doi.org/10.1016/j.tet.2004.07.001.

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16

Hassner, Alfred, Guy Patchornik, Tarun K. Pradhan, and R. Kumareswaran. "Intermolecular Electrophilic O-Amination of Alcohols†." Journal of Organic Chemistry 72, no. 2 (2007): 658–61. http://dx.doi.org/10.1021/jo061900m.

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17

Jin, Rongwei, Christina L. Bub, and Frederic W. Patureau. "Phenothiazinimides: Atom-Efficient Electrophilic Amination Reagents." Organic Letters 20, no. 10 (2018): 2884–87. http://dx.doi.org/10.1021/acs.orglett.8b00914.

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18

Gosmini, Corinne, and Martin Corpet. "Recent Advances in Electrophilic Amination Reactions." Synthesis 46, no. 17 (2014): 2258–71. http://dx.doi.org/10.1055/s-0034-1378373.

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19

Niwa, Yasuki, Kazuki Takayama, and Makoto Shimizu. "ChemInform Abstract: Electrophilic Amination with Iminomalonate." ChemInform 32, no. 43 (2010): no. http://dx.doi.org/10.1002/chin.200143060.

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20

Starkov, Pavel, Timothy F. Jamison, and Ilan Marek. "Electrophilic Amination: The Case of Nitrenoids." Chemistry - A European Journal 21, no. 14 (2015): 5278–300. http://dx.doi.org/10.1002/chem.201405779.

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21

Zhang, Qian, Kenshiro Hitoshio, Hayate Saito, Jun Shimokawa, and Hideki Yorimitsu. "Copper-Catalyzed Electrophilic Amination of Alkoxyarylsilanes." European Journal of Organic Chemistry 2020, no. 26 (2020): 4018–21. http://dx.doi.org/10.1002/ejoc.202000562.

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22

Usman, Muhammad, Xiao-Wen Zhang, Di Wu, Zheng-Hui Guan, and Wen-Bo Liu. "Application of dialkyl azodicarboxylate frameworks featuring multi-functional properties." Organic Chemistry Frontiers 6, no. 11 (2019): 1905–28. http://dx.doi.org/10.1039/c9qo00017h.

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23

Kassin, Victor-Emmanuel H., Romain Morodo, Thomas Toupy та ін. "A modular, low footprint and scalable flow platform for the expedient α-aminohydroxylation of enolizable ketones". Green Chemistry 23, № 6 (2021): 2336–51. http://dx.doi.org/10.1039/d0gc04395h.

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24

Zhu, Haibo, Yajing Shen, Qinyue Deng, and Tao Tu. "Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature." Chemical Communications 51, no. 92 (2015): 16573–76. http://dx.doi.org/10.1039/c5cc06069a.

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25

Lau, Yan-Fung, Chun-Ming Chan, Zhongyuan Zhou, and Wing-Yiu Yu. "Cp*Rh(iii)-catalyzed electrophilic amination of arylboronic acids with azo compounds for synthesis of arylhydrazides." Organic & Biomolecular Chemistry 14, no. 28 (2016): 6821–25. http://dx.doi.org/10.1039/c6ob00719h.

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26

Ning, Yingtang, Masatoshi Kawahata, Kentaro Yamaguchi, Yuko Otani, and Tomohiko Ohwada. "Synthesis, structure and N–N bonding character of 1,1-disubstituted indazolium hexafluorophosphate." Chemical Communications 54, no. 15 (2018): 1881–84. http://dx.doi.org/10.1039/c8cc00183a.

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27

Wang, Juping, Rongxing Xiao, Kangcheng Zheng, and Li Qian. "Theoretical studies on iron-catalyzed azaindoline formation: mechanism and site-selectivity." Dalton Transactions 50, no. 33 (2021): 11370–75. http://dx.doi.org/10.1039/d1dt02373j.

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28

Huo, Jingfeng, Yazhen Xue, and Jianbo Wang. "Regioselective copper-catalyzed aminoborylation of styrenes with bis(pinacolato)diboron and diazo compounds." Chemical Communications 54, no. 86 (2018): 12266–69. http://dx.doi.org/10.1039/c8cc07764a.

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29

Sadamitsu, Yuta, Kodai Saito, and Tohru Yamada. "Stereoselective amination via vinyl-silver intermediates derived from silver-catalyzed carboxylative cyclization of propargylamine." Chemical Communications 56, no. 66 (2020): 9517–20. http://dx.doi.org/10.1039/d0cc02273j.

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The stereoselective synthesis of aminovinyloxazolidinones based on the electrophilic amination of a vinyl-silver intermediate, generated by silver-catalyzed carbon dioxide incorporation on a propargylamine, was achieved.
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30

Ghoraf, Mohammed, and Joëlle Vidal. "Electrophilic amination of diorganozinc reagents by oxaziridines." Tetrahedron Letters 49, no. 52 (2008): 7383–85. http://dx.doi.org/10.1016/j.tetlet.2008.10.049.

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31

Johnson, Jeffrey S., and Ashley M. Berman. "Nickel-Catalyzed Electrophilic Amination of Organozinc Halides." Synlett, no. 11 (2005): 1799–801. http://dx.doi.org/10.1055/s-2005-871567.

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32

Lalic, Gojko, and Richard Rucker. "Copper-Catalyzed Electrophilic Amination of Organoboron Compounds." Synlett 24, no. 03 (2012): 269–75. http://dx.doi.org/10.1055/s-0032-1317744.

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33

Berman, Ashley M., and Jeffrey S. Johnson. "Copper-Catalyzed Electrophilic Amination of Diorganozinc Reagents." Journal of the American Chemical Society 126, no. 18 (2004): 5680–81. http://dx.doi.org/10.1021/ja049474e.

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34

GOUVERNEUR, V., and L. GHOSEZ. "ChemInform Abstract: Electrophilic Amination of 2-Azadienes." ChemInform 27, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199638092.

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35

Velarde-Ortiz, Raffet, Albert Guijarro, and Reuben D. Rieke. "ChemInform Abstract: Electrophilic Amination of Organozinc Halides." ChemInform 30, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199909067.

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36

GRECK, C., and J. P. GENET. "ChemInform Abstract: Electrophilic Amination: New Synthetic Applications." ChemInform 28, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199744301.

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37

Daşkapan, Tahir, Ferhat Yeşilbağ, and Selçuk Koca. "Cosolvent-promoted electrophilic amination of organozinc reagents." Applied Organometallic Chemistry 23, no. 6 (2009): 213–18. http://dx.doi.org/10.1002/aoc.1498.

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38

Xiao, Qing, Leiming Tian, Renchang Tan, et al. "Transition-Metal-Free Electrophilic Amination of Arylboroxines." Organic Letters 14, no. 16 (2012): 4230–33. http://dx.doi.org/10.1021/ol301912a.

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39

Yoon, Hongju, Yuna Kim, and Yunmi Lee. "Cu-Catalyzed electrophilic amination of internal alkynes via hydroalumination." Organic & Biomolecular Chemistry 15, no. 4 (2017): 790–95. http://dx.doi.org/10.1039/c6ob02606k.

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A straightforward and efficient method for the synthesis of 1,2-diaryl-substituted enamines through the Cu-catalyzed electrophilic amination reaction of O-benzoyl hydroxylamines with vinylaluminum reagents generated in situ from the Ni-catalyzed hydroalumination of readily accessible internal aryl acetylenes is described.
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40

Dumoulin, Audrey, Claudia Lalli, Pascal Retailleau, and Géraldine Masson. "Catalytic, highly enantioselective, direct amination of enecarbamates." Chemical Communications 51, no. 25 (2015): 5383–86. http://dx.doi.org/10.1039/c4cc08052a.

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Highly enantioselective electrophilic amination reaction of enecarbamates with dibenzylazodicarboxylate and oxygenated nucleophiles catalyzed by chiral phosphoric acids is reported. Subsequent reduction or oxidation of the resulting precursors of α-hydrazinoimines leads to 1,2-diamines or α-amino acid precursors, respectively, in excellent yields and enantioselectivities.
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41

Denmark, Scott E., Naoto Chatani, and Sunil V. Pansare. "Asymmetric electrophilic amination of chiral phosphorus-stabilized anions." Tetrahedron 48, no. 11 (1992): 2191–208. http://dx.doi.org/10.1016/s0040-4020(01)88883-9.

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42

Matsuda, Naoki, Koji Hirano, Tetsuya Satoh, and Masahiro Miura. "An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles." Journal of Organic Chemistry 77, no. 1 (2011): 617–25. http://dx.doi.org/10.1021/jo202207s.

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43

Berman, Ashley M., and Jeffrey S. Johnson. "Copper-Catalyzed Electrophilic Amination of Functionalized Diarylzinc Reagents." Journal of Organic Chemistry 70, no. 1 (2005): 364–66. http://dx.doi.org/10.1021/jo048168g.

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44

Mamone, Marius, Estelle Morvan, Thierry Milcent, Sandrine Ongeri, and Benoit Crousse. "Electrophilic Amination of Fluoroalkyl Groups on Azodicarboxylate Derivatives." Journal of Organic Chemistry 80, no. 3 (2015): 1964–71. http://dx.doi.org/10.1021/jo502638y.

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45

Armstrong, Alan, Mark A. Atkin, and Steven Swallow. "Electrophilic amination of carbanions by N-carboxamido oxaziridines." Tetrahedron Letters 41, no. 13 (2000): 2247–51. http://dx.doi.org/10.1016/s0040-4039(00)00140-4.

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46

Gmeiner, Peter, та Bernd Bollinger. "Asymmetric synthesis of β-aminotetralins by electrophilic amination". Tetrahedron 50, № 37 (1994): 10909–22. http://dx.doi.org/10.1016/s0040-4020(01)85702-1.

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47

Smulik, Jason A., and Edwin Vedejs. "Improved Reagent for Electrophilic Amination of Stabilized Carbanions." Organic Letters 5, no. 22 (2003): 4187–90. http://dx.doi.org/10.1021/ol035629w.

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48

KUZ'MENKO, V. V., and A. F. POZHARSKII. "ChemInform Abstract: Electrophilic N-Amination of vic-Triazole." ChemInform 24, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199316127.

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49

Qian, Xin, Zailu Yu, Audrey Auffrant, and Corinne Gosmini. "Cobalt-Catalyzed Electrophilic Amination of Arylzincs withN-Chloroamines." Chemistry - A European Journal 19, no. 20 (2013): 6225–29. http://dx.doi.org/10.1002/chem.201300229.

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50

Lee, Sangback, and Yunmi Lee. "Copper-Catalyzed Electrophilic Amination of Benzoxazoles via Magnesation." European Journal of Organic Chemistry 2019, no. 19 (2019): 3045–50. http://dx.doi.org/10.1002/ejoc.201900335.

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