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Journal articles on the topic 'Carboaminaion'

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Author: Grafiati

Published: 9 March 2023

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1

Chen, Xiang, Fang Xiao, and Wei-Min He. "Recent developments in the difunctionalization of alkenes with C–N bond formation." Organic Chemistry Frontiers 8, no. 18 (2021): 5206–28. http://dx.doi.org/10.1039/d1qo00375e.

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2

You, Cai, and Armido Studer. "Three-component 1,2-carboamination of vinyl boronic esters via amidyl radical induced 1,2-migration." Chemical Science 12, no. 47 (2021): 15765–69. http://dx.doi.org/10.1039/d1sc05811h.

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3

Jiang, Heng, and Armido Studer. "Intermolecular radical carboamination of alkenes." Chemical Society Reviews 49, no. 6 (2020): 1790–811. http://dx.doi.org/10.1039/c9cs00692c.

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4

Liu, Zhenhua, Huimin Ji, Wen Gao, Guangyu Zhu, Lili Tong, Fengcai Lei, and Bo Tang. "Copper(i)-mediated carboamination of vinyl azides by aryldiazonium salts: synthesis of N2-substituted 1,2,3-triazoles." Chemical Communications 53, no. 46 (2017): 6259–62. http://dx.doi.org/10.1039/c7cc02391j.

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5

Wang, Wei, Jun-Rong Song, Zhi-Yao Li, Ting Zhong, Qin Chi, Hai Ren, and Wei-Dong Pan. "Copper-catalyzed aerobic oxidative radical alkoxycyclization of tryptamines to access 3-alkoxypyrroloindolines." RSC Advances 11, no. 29 (2021): 18080–83. http://dx.doi.org/10.1039/d1ra02679h.

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6

Hopkins, B. A., and J. P. Wolfe. "Enantioselective synthesis of tetrahydroquinolines, tetrahydroquinoxalines, and tetrahydroisoquinolines via Pd-Catalyzed alkene carboamination reactions." Chem. Sci. 5, no. 12 (2014): 4840–44. http://dx.doi.org/10.1039/c4sc01327a.

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Asymmetric palladium-catalyzed carboamination reactions of aminoalkene substrates provide substituted six-membered heterocycles bearing quaternary stereocenters in good yield and high enantioselectivity.

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7

Gan, Zixu, Ke Zhang, Peng Shi, Yingsheng Zhao, and Runsheng Zeng. "Copper(i)-catalyzed radical carboamination reaction of 8-aminoquinoline-oriented buteneamides with chloroform: synthesis of-β-lactams." RSC Advances 11, no. 45 (2021): 28081–84. http://dx.doi.org/10.1039/d1ra05233k.

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8

Dai, Chenshu, Siqi Deng, Qiuhua Zhu, and Xiaodong Tang. "Synthesis of pyrrolo[1,2-a]quinoxalines via copper or iron-catalyzed aerobic oxidative carboamination of sp3C–H bonds." RSC Advances 7, no. 70 (2017): 44132–35. http://dx.doi.org/10.1039/c7ra09214h.

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9

Gazzotti, Stefano, Marco Manenti, Leonardo Lo Presti, and Alessandra Silvani. "Allylation of isatin-derived N-Boc-hydrazones followed by Pd-catalyzed carboamination reaction: an entry to 3-spiro-pyrazolidyl-oxindoles." RSC Advances 9, no. 65 (2019): 37788–800. http://dx.doi.org/10.1039/c9ra07712j.

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The indium-mediated allylation of novel 3-(2-Boc-hydrazono)indolin-2-one derivatives, followed by a palladium-catalysed carboamination reaction, is described to afford unprecedented spirocyclic oxindoles in good yields.

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10

Wolfe, John, and Zachary Garlets. "Asymmetric Synthesis of Six-Membered Cyclic Sulfamides via Palladium-Catalyzed Alkene Carboamination Reactions." Synthesis 50, no. 22 (May 3, 2018): 4444–52. http://dx.doi.org/10.1055/s-0036-1591574.

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The asymmetric synthesis of six-membered cyclic sulfamides via palladium-catalyzed alkene carboamination reactions of N-homoallylsulfamides with aryl halides is described. High levels of enantioselectivity were obtained with a catalyst composed of Pd2dba3 and (S)-Siphos-PE.

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11

Wang, Yuzhuo, Lei Wang, Mingjie Chen, Youshao Tu, Yu Liu, and Junliang Zhang. "Palladium/Xu-Phos-catalyzed asymmetric carboamination towards isoxazolidines and pyrrolidines." Chemical Science 12, no. 23 (2021): 8241–45. http://dx.doi.org/10.1039/d1sc01337h.

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The new chiral ligand (S,Rs)-Xu4 with ortho-OⁱPr showed good performance in the asymmetric carboamination reaction of N-Boc-O-homoallyl-hydroxylamines and N-Boc-pent-4-enylamines with aryl or alkenyl bromides.

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12

Zhang, Yu, Haidong Liu, Luning Tang, Hai-Jun Tang, Lu Wang, Chuan Zhu, and Chao Feng. "Intermolecular Carboamination of Unactivated Alkenes." Journal of the American Chemical Society 140, no. 34 (August 13, 2018): 10695–99. http://dx.doi.org/10.1021/jacs.8b07023.

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13

Kanazawa, Junichiro, and Masanobu Uchiyama. "Recent Advances in the Synthetic Chemistry of Bicyclo[1.1.1]pentane." Synlett 30, no. 01 (November 15, 2018): 1–11. http://dx.doi.org/10.1055/s-0037-1610314.

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Utilization of three-dimensional cyclic scaffolds is important in modern drug discovery, both to provide greater opportunities for optimizing drug candidates and to expand the available chemical space of drugs. Among these scaffolds, bicyclo[1.1.1]pentane (BCP) is a high-value bioisostere for 1,4-disubstituted phenyl rings, internal alkynes, and the tert-butyl group, generally offering high passive permeability, high water solubility, and improved metabolic stability. However, the lack of methods for functionalizing BCP remains a significant challenge, and in particular, a versatile strategy for synthesizing a wide range of unsymmetrically 1,3-difunctionalized BCP derivatives has been lacking. In this account, we review recent advances in the synthetic chemistry of BCP, focusing especially on our recently developed radical multicomponent carboamination of [1.1.1]propellane.1 Introduction2 Overview of the Synthetic Chemistry of [1.1.1]Propellane, the Most Promising Precursor of Bicyclo[1.1.1]pentane3 Recent Advances in the Synthetic Chemistry of Unsymmetrically 1,3-Disubstituted Bicyclo[1.1.1]pentane Derivatives4 Radical Multicomponent Carboamination of [1.1.1]Propellane Permits Direct Synthesis of 3-Substituted Bicyclo[1.1.1]pent-1-ylamine Derivatives5 Conclusion

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14

Okumura, Mikiko, Alexander S. Shved, and David Sarlah. "Palladium-Catalyzed Dearomative syn-1,4-Carboamination." Journal of the American Chemical Society 139, no. 49 (December 5, 2017): 17787–90. http://dx.doi.org/10.1021/jacs.7b11663.

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15

Kanazawa, Junichiro, Katsuya Maeda, and Masanobu Uchiyama. "Radical Multicomponent Carboamination of [1.1.1]Propellane." Journal of the American Chemical Society 139, no. 49 (November 28, 2017): 17791–94. http://dx.doi.org/10.1021/jacs.7b11865.

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16

Hernandez, Lucas W., Ulrich Klöckner, Jola Pospech, Lilian Hauss, and David Sarlah. "Nickel-Catalyzed Dearomative trans-1,2-Carboamination." Journal of the American Chemical Society 140, no. 13 (March 15, 2018): 4503–7. http://dx.doi.org/10.1021/jacs.8b01726.

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17

Wolfe, J., J. Nakhla, and J. Kampf. "Intramolecular Pd-Catalyzed Carboetherification and Carboamination." Synfacts 2006, no. 7 (June 2006): 0677. http://dx.doi.org/10.1055/s-2006-941809.

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18

Kang, Taeho, Nana Kim, Peter T. Cheng, Hao Zhang, Klement Foo, and Keary M. Engle. "Nickel-Catalyzed 1,2-Carboamination of Alkenyl Alcohols." Journal of the American Chemical Society 143, no. 34 (August 20, 2021): 13962–70. http://dx.doi.org/10.1021/jacs.1c07112.

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19

Gockel, Samuel N., Travis L. Buchanan, and Kami L. Hull. "Cu-Catalyzed Three-Component Carboamination of Alkenes." Journal of the American Chemical Society 140, no. 1 (December 28, 2017): 58–61. http://dx.doi.org/10.1021/jacs.7b10529.

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20

Heinrich, M., O. Blank, and S. Wölfel. "Reductive Carboamination of Olefins with Aryldiazonium Salts." Synfacts 2006, no. 10 (September 2006): 1045. http://dx.doi.org/10.1055/s-2006-949308.

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21

Chemler, S., L. Miao, I. Haque, M. Manzoni, and W. Tham. "Enantioselective Copper-Catalyzed Intramolecular Carboamination of Alkenes." Synfacts 2011, no. 02 (January 19, 2011): 0185. http://dx.doi.org/10.1055/s-0030-1259271.

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22

Heinrich, Markus R., and Nina Diesendorf. "Current Advances in Meerwein-type Radical Alkene Functionalizations." Synthesis 54, no. 08 (March 2, 2022): 1951–63. http://dx.doi.org/10.1055/s-0040-1719893.

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AbstractAlkene functionalizations via Meerwein arylations are becoming increasingly attractive, especially since a variety of mild and sustainable methods for aryl radical generation are available today. This entails a broad spectrum of substrates and radical scavengers, as well as convenient synthetic routes to relevant precursors for further transformations. The present review focuses on recent advances in Meerwein-type alkene functionalizations and gives insights into the key mechanistic details of the respective reactions.1 Introduction2 Hydroarylation and Carboarylation3 Carboamination, Carbooxygenation, and Carbothiolation4 Carbohalogenation5 Conclusion and Outlook

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23

Christodoulou, Michael S., Egle M. Beccalli, and Sabrina Giofrè. "Palladium-Catalyzed Benzodiazepines Synthesis." Catalysts 10, no. 6 (June 6, 2020): 634. http://dx.doi.org/10.3390/catal10060634.

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This review is focused on palladium-catalyzed reactions as efficient strategies aimed at the synthesis of different classes of benzodiazepines. Several reaction typologies are reported including hydroamination, amination, C–H arylation, N-arylation, and the Buchwald–Hartwig reaction, depending on the different substrates identified as halogenated starting materials (activated substrates) or unactivated unsaturated systems, which then exploit Pd(0)- or Pd(II)-catalytic species. In particular, the use of the domino reactions, as intra- or intermolecular processes, are reported as an efficient and eco-compatible tool to obtain differently functionalized benzodiazepines. Different domino reaction typologies are the carboamination, aminoarylation, aminoacethoxylation, aminohalogenation, and aminoazidation.

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24

Zeng, Wei, and Sherry R. Chemler. "Copper(II)-Catalyzed Enantioselective Intramolecular Carboamination of Alkenes." Journal of the American Chemical Society 129, no. 43 (October 2007): 12948–49. http://dx.doi.org/10.1021/ja0762240.

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25

Rossiter, Lana M., Meagan L. Slater, Rachel E. Giessert, Samuel A. Sakwa, and R. Jason Herr. "A Concise Palladium-Catalyzed Carboamination Route to (±)-Tylophorine." Journal of Organic Chemistry 74, no. 24 (December 18, 2009): 9554–57. http://dx.doi.org/10.1021/jo902114u.

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26

Wolfe, J., and N. Bbaij. "Synthesis of Bicyclic Ureas via Palladium-Catalyzed Carboamination." Synfacts 10, no. 01 (December 13, 2013): 0110. http://dx.doi.org/10.1055/s-0033-1340507.

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27

Wolfe, J., and D. Mai. "Synthesis of Chiral Pyrrolidines by Palladium-Catalyzed Carboamination." Synfacts 2010, no. 11 (October 21, 2010): 1227. http://dx.doi.org/10.1055/s-0030-1258836.

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28

Casavant, Barbara J., Azade S. Hosseini, and Sherry R. Chemler. "6-Azabicyclo[3.2.1]octanesviaCopper-Catalyzed Enantioselective Alkene Carboamination." Advanced Synthesis & Catalysis 356, no. 11-12 (June 25, 2014): 2697–702. http://dx.doi.org/10.1002/adsc.201400317.

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29

Gockel, Samuel N., SangHyun Lee, Brittany L. Gay, and Kami L. Hull. "Oxidative Three-Component Carboamination of Vinylarenes with Alkylboronic Acids." ACS Catalysis 11, no. 9 (April 14, 2021): 5166–71. http://dx.doi.org/10.1021/acscatal.1c00105.

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30

Gockel, Samuel N., Travis L. Buchanan, and Kami L. Hull. "Correction to “Cu-Catalyzed Three-Component Carboamination of Alkenes”." Journal of the American Chemical Society 143, no. 15 (April 6, 2021): 6019–20. http://dx.doi.org/10.1021/jacs.1c03077.

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31

Zavesky, Blane P., Nicholas R. Babij, Jonathan A. Fritz, and John P. Wolfe. "Synthesis of Cyclic Guanidines via Pd-Catalyzed Alkene Carboamination." Organic Letters 15, no. 21 (October 22, 2013): 5420–23. http://dx.doi.org/10.1021/ol402377y.

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32

Liu, Zhen, Yanyan Wang, Zichen Wang, Tian Zeng, Peng Liu, and Keary M. Engle. "Catalytic Intermolecular Carboamination of Unactivated Alkenes via Directed Aminopalladation." Journal of the American Chemical Society 139, no. 32 (August 4, 2017): 11261–70. http://dx.doi.org/10.1021/jacs.7b06520.

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33

Bizet, Vincent, Gustavo M. Borrajo-Calleja, Céline Besnard, and Clément Mazet. "Direct Access to Furoindolines by Palladium-Catalyzed Intermolecular Carboamination." ACS Catalysis 6, no. 10 (September 27, 2016): 7183–87. http://dx.doi.org/10.1021/acscatal.6b02238.

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34

Yoshino, Yasufumi, Takuya Kurahashi, and Seijiro Matsubara. "Nickel-Catalyzed Decarboxylative Carboamination of Alkynes with Isatoic Anhydrides." Journal of the American Chemical Society 131, no. 22 (June 10, 2009): 7494–95. http://dx.doi.org/10.1021/ja900805y.

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35

He, Jun, Yuhang Xue, Bo Han, Chunzhu Zhang, You Wang, and Shaolin Zhu. "Nickel‐Catalyzed Asymmetric Reductive 1,2‐Carboamination of Unactivated Alkenes." Angewandte Chemie 132, no. 6 (December 27, 2019): 2348–52. http://dx.doi.org/10.1002/ange.201913743.

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36

Tang, Conghui, Mikiko Okumura, Yunbo Zhu, Annie R. Hooper, Yu Zhou, Yu‐Hsuan Lee, and David Sarlah. "Palladium‐Catalyzed Dearomative syn ‐1,4‐Carboamination with Grignard Reagents." Angewandte Chemie International Edition 58, no. 30 (July 22, 2019): 10245–49. http://dx.doi.org/10.1002/anie.201905021.

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37

He, Jun, Yuhang Xue, Bo Han, Chunzhu Zhang, You Wang, and Shaolin Zhu. "Nickel‐Catalyzed Asymmetric Reductive 1,2‐Carboamination of Unactivated Alkenes." Angewandte Chemie International Edition 59, no. 6 (February 3, 2020): 2328–32. http://dx.doi.org/10.1002/anie.201913743.

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38

Tang, Conghui, Mikiko Okumura, Yunbo Zhu, Annie R. Hooper, Yu Zhou, Yu‐Hsuan Lee, and David Sarlah. "Palladium‐Catalyzed Dearomative syn ‐1,4‐Carboamination with Grignard Reagents." Angewandte Chemie 131, no. 30 (June 24, 2019): 10351–55. http://dx.doi.org/10.1002/ange.201905021.

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39

Richards, Corey A., Nigam P. Rath, and Jamie M. Neely. "Iron-Catalyzed Alkyne Carboamination via an Isolable Iron Imide Complex." Organometallics 40, no. 17 (August 18, 2021): 2945–50. http://dx.doi.org/10.1021/acs.organomet.1c00454.

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40

Fürstner, Alois, and Paul W. Davies. "Heterocycles by PtCl2-Catalyzed Intramolecular Carboalkoxylation or Carboamination of Alkynes." Journal of the American Chemical Society 127, no. 43 (November 2005): 15024–25. http://dx.doi.org/10.1021/ja055659p.

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41

Xiong, Yang, Xiaodong Ma, and Guozhu Zhang. "Copper-Catalyzed Intermolecular Carboamination of Alkenes Induced by Visible Light." Organic Letters 21, no. 6 (February 25, 2019): 1699–703. http://dx.doi.org/10.1021/acs.orglett.9b00252.

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42

Kindt, Stephanie, Karina Wicht, and Markus R. Heinrich. "Base-Induced Radical Carboamination of Nonactivated Alkenes with Aryldiazonium Salts." Organic Letters 17, no. 24 (December 4, 2015): 6122–25. http://dx.doi.org/10.1021/acs.orglett.5b03143.

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43

Belov, G. M., D. S. Belov, A. V. Kurkin, and M. A. Yurovskaya. "Palladium-catalyzed carboamination in the synthesis of nitrogen-containing heterocycles." Chemistry of Heterocyclic Compounds 48, no. 1 (April 2012): 73–81. http://dx.doi.org/10.1007/s10593-012-0971-9.

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44

Neukom, Joshua D., Alvin S. Aquino, and John P. Wolfe. "Synthesis of Saturated 1,4-Benzodiazepines via Pd-Catalyzed Carboamination Reactions." Organic Letters 13, no. 9 (May 6, 2011): 2196–99. http://dx.doi.org/10.1021/ol200429a.

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45

Mai, Duy N., Brandon R. Rosen, and John P. Wolfe. "Enantioconvergent Synthesis of (+)-Aphanorphine via Asymmetric Pd-Catalyzed Alkene Carboamination." Organic Letters 13, no. 11 (June 3, 2011): 2932–35. http://dx.doi.org/10.1021/ol2009895.

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46

van der Puyl, Vincent A., Joseph Derosa, and Keary M. Engle. "Directed, Nickel-Catalyzed Umpolung 1,2-Carboamination of Alkenyl Carbonyl Compounds." ACS Catalysis 9, no. 1 (December 6, 2018): 224–29. http://dx.doi.org/10.1021/acscatal.8b04516.

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47

Zeng, Wei, and Sherry R. Chemler. "Total Synthesis of (S)-(+)-Tylophorine Via Enantioselective Intramolecular Alkene Carboamination." Journal of Organic Chemistry 73, no. 15 (August 2008): 6045–47. http://dx.doi.org/10.1021/jo801024h.

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48

Jiang, Heng, Gesa Seidler, and Armido Studer. "Carboamination of Unactivated Alkenes through Three‐Component Radical Conjugate Addition." Angewandte Chemie 131, no. 46 (October 11, 2019): 16680–84. http://dx.doi.org/10.1002/ange.201910926.

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49

Jiang, Heng, Gesa Seidler, and Armido Studer. "Carboamination of Unactivated Alkenes through Three‐Component Radical Conjugate Addition." Angewandte Chemie International Edition 58, no. 46 (November 11, 2019): 16528–32. http://dx.doi.org/10.1002/anie.201910926.

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50

Guo, Yajing, Jinbo Zhao, and Qian Zhang. "Synthesis of Tetrahydropyridazines via Pd‐Catalyzed Carboamination of Alkenyl Hydrazones." Advanced Synthesis & Catalysis 362, no. 5 (January 28, 2020): 1208–12. http://dx.doi.org/10.1002/adsc.201901378.

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