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Journal articles on the topic 'Hydroamination'

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Author: Grafiati

Published: 4 June 2021

Last updated: 22 June 2024

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1

Tobisch, Sven. "CuH-catalysed hydroamination of arylalkynes with hydroxylamine esters – a computational scrutiny of rival mechanistic pathways." Chemical Science 8, no. 6 (2017): 4410–23. http://dx.doi.org/10.1039/c7sc01107e.

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An in-depth computational mechanistic probe of the CuH-mediated hydroamination of internal arylalkynes with amine electrophile and hydrosilane defines the most accessible pathways for rival avenues of direct and reductive hydroamination, from which a general understanding of the factors controlling formal hydroamination catalysis emerges.

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2

Li, Ping, Boon Chong Lee, Ming Joo Koh, and Xiaoxiang Zhang. "Base-Mediated Site-Selective Hydroamination of Alkenes." Synthesis 54, no. 06 (October 28, 2021): 1566–76. http://dx.doi.org/10.1055/a-1681-4720.

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AbstractWe present a base-mediated hydroamination protocol, using substoichiometric amounts of a hydrosilane and potassium tert-butoxide, that operates under mild conditions at 30 °C. Many aryl- and heteroatom-substituted olefins as well as arylamines are tolerated, affording the desired products with complete regioselectivity. Preliminary mechanistic investigations reveal a non-radical pathway for hydroamination. A sequential remote hydroamination strategy involving an initial Fe-catalysed olefin isomerisation followed by our base-mediated hydroamination was also developed to directly access β-arylamines from terminal aliphatic alkenes.

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3

Yang, Song, Quan-Zhe Li, Chen Xu, Qin Xu, and Min Shi. "Rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes." Chemical Science 9, no. 22 (2018): 5074–81. http://dx.doi.org/10.1039/c8sc01595c.

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A novel rhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes has been developed, affording the hydroamination and hydroindolation products in good to excellent yields with outstanding ee values through a new TMM–Rh model complex.

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4

Tobisch, Sven. "Aluminium-catalysed intramolecular hydroamination of aminoalkenes: computational perusal of alternative pathways for aminoalkene activation." Dalton Transactions 44, no. 27 (2015): 12169–79. http://dx.doi.org/10.1039/c5dt00121h.

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Rival mechanistic pathways for CC bond activation in aluminium-catalysed hydroamination: computational mechanistic analysis reveals that a catalytically relevant [(pda)Al(NHR)] compound promotes hydroamination through a stepwise σ-bond insertive mechanism with turnover-limiting aminolysis.

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5

Palchak, Zachary L., Daniel J. Lussier, Conor J. Pierce, Hoseong Yoo, and Catharine H. Larsen. "Catalytic Tandem Markovnikov Hydroamination-Alkynylation and Markovnikov Hydroamination-Hydrovinylation." Advanced Synthesis & Catalysis 357, no. 2-3 (January 30, 2015): 539–48. http://dx.doi.org/10.1002/adsc.201401037.

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6

Suleymanov, Yury. "Anti-Markovnikov hydroamination." Science 366, no. 6467 (November 14, 2019): 834.2–834. http://dx.doi.org/10.1126/science.366.6467.834-b.

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7

Hong, Sukwon, and Tobin J. Marks. "Organolanthanide-Catalyzed Hydroamination." Accounts of Chemical Research 37, no. 9 (September 2004): 673–86. http://dx.doi.org/10.1021/ar040051r.

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8

Ogasawara, M., T. Takahashi, W. Lin, A. Hu, T. Sakamoto, A. Okada, and K. Nakajima. "Intermolecular Asymmetric Hydroamination." Synfacts 2007, no. 1 (January 2007): 0049. http://dx.doi.org/10.1055/s-2006-955723.

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9

Shibuya, Masatoshi, Shohei Kawano, Shoji Fujita, and Yoshihiko Yamamoto. "Boron‐Catalyzed Hydroamination/Hydroallylation and Hydroamination/Hydrocyanation of Unactivated Alkynes." Asian Journal of Organic Chemistry 8, no. 7 (May 21, 2019): 1075–79. http://dx.doi.org/10.1002/ajoc.201900165.

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10

Casnati, Alessandra, Aleksandr Voronov, Damiano Giuseppe Ferrari, Raffaella Mancuso, Bartolo Gabriele, Elena Motti, and Nicola Della Ca’. "PdI2 as a Simple and Efficient Catalyst for the Hydroamination of Arylacetylenes with Anilines." Catalysts 10, no. 2 (February 2, 2020): 176. http://dx.doi.org/10.3390/catal10020176.

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The hydroamination reaction is a convenient alternative strategy for the formation of C–N bonds. Herein, we report a new versatile and convenient protocol for the hydroamination of arylacetylenes with anilines using palladium iodide in the absence of any added ligand as catalyst. Mild conditions, excellent regio- and stereoselectivity, and high functional group tolerance are the main features of this methodology. A subsequent reduction step gives access to a wide variety of secondary aromatic amines.

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11

Hirano, Koji, and Masahiro Miura. "Copper-catalyzed aminoboration and hydroamination of alkenes with electrophilic amination reagents." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 291–97. http://dx.doi.org/10.1515/pac-2014-5004.

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Abstract A copper-catalyzed regioselective, stereospecific, and enantioselective aminoboration reaction of alkenes with bis(pinacolato)diboron and O-acylated hydroxylamines has been developed to deliver the corresponding β-aminoalkylboranes, which can be important building blocks in organic synthesis. In addition, this methodology has been applied to a formal regioselective hydroamination of styrenes by replacement of the diboron reagent with polymethylhydrosiloxane (PMHS). The catalytic asymmetric hydroamination is also possible by using an appropriate chiral biphosphine ligand.

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12

Palchak, Zachary L., Daniel J. Lussier, Conor J. Pierce, Hoseong Yoo, and Catharine H. Larsen. "ChemInform Abstract: Catalytic Tandem Markovnikov Hydroamination-Alkynylation and Markovnikov Hydroamination-Hydrovinylation." ChemInform 46, no. 26 (June 2015): no. http://dx.doi.org/10.1002/chin.201526044.

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13

Patil, Nitin T., Pediredla G. V. V. Lakshmi, and Vipender Singh. "AuI-Catalyzed Direct Hydroamination/Hydroarylation and Double Hydroamination of Terminal Alkynes." European Journal of Organic Chemistry 2010, no. 24 (July 13, 2010): 4719–31. http://dx.doi.org/10.1002/ejoc.201000389.

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14

Deng, Haiqin, Zikai He, Jacky W. Y. Lam, and Ben Zhong Tang. "Regio- and stereoselective construction of stimuli-responsive macromolecules by a sequential coupling-hydroamination polymerization route." Polymer Chemistry 6, no. 48 (2015): 8297–305. http://dx.doi.org/10.1039/c5py01424g.

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15

Deng, Haiqin, Engui Zhao, Anakin C. S. Leung, Rongrong Hu, Yun Zhang, Jacky W. Y. Lam, and Ben Zhong Tang. "Multicomponent sequential polymerizations of alkynes, carbonyl chloride and amino ester salts toward helical and luminescent polymers." Polymer Chemistry 7, no. 9 (2016): 1836–46. http://dx.doi.org/10.1039/c6py00024j.

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16

Kissel, Alexander A., Tatyana V. Mahrova, Dmitry M. Lyubov, Anton V. Cherkasov, Georgy K. Fukin, Alexander A. Trifonov, Iker Del Rosal, and Laurent Maron. "Metallacyclic yttrium alkyl and hydrido complexes: synthesis, structures and catalytic activity in intermolecular olefin hydrophosphination and hydroamination." Dalton Transactions 44, no. 27 (2015): 12137–48. http://dx.doi.org/10.1039/c5dt00129c.

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17

Xu, Kun, Yu-Hsuan Wang, Vahid Khakyzadeh, and Bernhard Breit. "Asymmetric synthesis of allylic amines via hydroamination of allenes with benzophenone imine." Chemical Science 7, no. 5 (2016): 3313–16. http://dx.doi.org/10.1039/c5sc04984a.

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18

Reshetov, P. V., O. V. Fedotova, A. P. Kriven'ko, and V. G. Kharchenko. "Hydroamination of pyrylium salts." Chemistry of Heterocyclic Compounds 26, no. 5 (May 1990): 513–16. http://dx.doi.org/10.1007/bf00487423.

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19

Reznichenko, Alexander L., Agnieszka J. Nawara-Hultzsch, and Kai C. Hultzsch. "ChemInform Abstract: Asymmetric Hydroamination." ChemInform 46, no. 39 (September 2015): no. http://dx.doi.org/10.1002/chin.201539235.

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20

Reznichenko, Alexander L., and Kai C. Hultzsch. "ChemInform Abstract: Asymmetric Hydroamination." ChemInform 42, no. 45 (October 13, 2011): no. http://dx.doi.org/10.1002/chin.201145232.

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21

Hartwig, J. F. "Development of catalysts for the hydroamination of olefins." Pure and Applied Chemistry 76, no. 3 (January 1, 2004): 507–16. http://dx.doi.org/10.1351/pac200476030507.

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Studies on the development of palladium, nickel, and rhodium catalysts for the hydroamination of dienes and vinylarenes are described. Enantioselective catalysts based on palladium have been developed for the addition of arylamines to dienes and for Markovnikov addition of arylamines to vinylarenes. In addition, nickel catalysts for the addition of aliphatic amines to dienes have been developed, and rhodium catalysts for the first transition metal-catalyzed aminations of vinylarenes that generate terminal amines as the major product are described. Mechanistic data on the hydroamination of vinylarenes with palladium and rhodium is also provided.

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22

Gallegos, Carlos, Ruth Camacho, Mercedes Valiente, Tomás Cuenca, and Jesús Cano. "Cyclopentadienyl-based Mg complexes in the intramolecular hydroamination of aminoalkenes: mechanistic evidence for cationic versus neutral magnesium derivatives." Catalysis Science & Technology 6, no. 13 (2016): 5134–43. http://dx.doi.org/10.1039/c5cy01040c.

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23

Tussing, Sebastian, Miriam Ohland, Garrit Wicker, Ulrich Flörke, and Jan Paradies. "Borane-catalyzed indole synthesis through intramolecular hydroamination." Dalton Transactions 46, no. 5 (2017): 1539–45. http://dx.doi.org/10.1039/c6dt04725d.

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24

Steiner, Matthias R., Johann A. Hlina, Johanna M. Uher, Roland C. Fischer, Dmytro Neshchadin, and Theresa Wilfling. "Phosphinoindenyl and phosphazidoindenyl complexes of lanthanum and samarium: synthesis, characterisation, and hydroamination catalysis." Dalton Transactions 51, no. 5 (2022): 1819–28. http://dx.doi.org/10.1039/d1dt03219d.

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25

Feng, Zhijun, Yun Wei, Shuangliu Zhou, Guangchao Zhang, Xiancui Zhu, Liping Guo, Shaowu Wang, and Xiaolong Mu. "Reactivity of functionalized indoles with rare-earth metal amides. Synthesis, characterization and catalytic activity of rare-earth metal complexes incorporating indolyl ligands." Dalton Transactions 44, no. 47 (2015): 20502–13. http://dx.doi.org/10.1039/c5dt03214h.

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26

Wu, Zhenzhen, Mei Zhang, Yu Shi, and Genping Huang. "Mechanism and origins of stereo- and enantioselectivities of palladium-catalyzed hydroamination of racemic internal allenes via dynamic kinetic resolution: a computational study." Organic Chemistry Frontiers 7, no. 12 (2020): 1502–11. http://dx.doi.org/10.1039/d0qo00174k.

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27

Sun, Peng, Jiaojiao Yang, Zirui Song, Yichao Cai, Yajie Liu, Chunxia Chen, Xin Chen, and Jinsong Peng. "Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction." Synthesis 52, no. 01 (November 5, 2019): 75–84. http://dx.doi.org/10.1055/s-0039-1690240.

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Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The initial hydroamination of anilines to ester arylpropiolates in benzene can proceed in a stereoselective manner to give ester (Z)-3-(arylamino)acrylates in the presence of CuCl2/phenanthroline, KMnO4, and KHCO3 at 120 °C. Sequentially, these in situ functionalized adducts can undergo direct intramolecular oxidative alkenylation of aromatic C–H bond in mixed solvents (benzene/DMSO 1:1) at 130 °C affording multi-substituted indoles in good to high yields.

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28

Foster, Daven, Pengchao Gao, Ziyun Zhang, Gellért Sipos, Alexandre N. Sobolev, Gareth Nealon, Laura Falivene, Luigi Cavallo, and Reto Dorta. "Design, scope and mechanism of highly active and selective chiral NHC–iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes." Chemical Science 12, no. 10 (2021): 3751–67. http://dx.doi.org/10.1039/d0sc05884j.

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29

Yu, Feng, Pinhong Chen, and Guosheng Liu. "Pd(ii)-catalyzed intermolecular enantioselective hydroamination of styrenes." Organic Chemistry Frontiers 2, no. 7 (2015): 819–22. http://dx.doi.org/10.1039/c5qo00096c.

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30

Krieck, Sven, Diana Kalden, Ansgar Oberheide, Lydia Seyfarth, Hans-Dieter Arndt, Helmar Görls, and Matthias Westerhausen. "Synthesis and catalytic activity of tridentate N-(2-pyridylethyl)-substituted bulky amidinates of calcium and strontium." Dalton Transactions 48, no. 7 (2019): 2479–90. http://dx.doi.org/10.1039/c8dt04905j.

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31

Schmid, Bernhard, Sibylle Frieß, Alberto Herrera, Anthony Linden, Frank W. Heinemann, Harald Locke, Sjoerd Harder, and Romano Dorta. "Chiral amino-phosphine and amido-phosphine complexes of Ir and Mg. Catalytic applications in olefin hydroamination." Dalton Transactions 45, no. 30 (2016): 12028–40. http://dx.doi.org/10.1039/c6dt01146b.

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32

Xu, Xuefeng, Xu Zhang, Zhiqiang Wang, and Manman Kong. "HOTf-catalyzed intermolecular hydroamination reactions of alkenes and alkynes with anilines." RSC Advances 5, no. 51 (2015): 40950–52. http://dx.doi.org/10.1039/c5ra05209b.

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33

Cacchi, Sandro, Giancarlo Fabrizi, Andrea Fochetti, Francesca Ghirga, Antonella Goggiamani, and Antonia Iazzetti. "Stereo- and regioselective gold(i)-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines." Organic & Biomolecular Chemistry 17, no. 3 (2019): 527–32. http://dx.doi.org/10.1039/c8ob02356e.

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34

Chen, Jun, Hong-Mei Guo, Quan-Qing Zhao, Jia-Rong Chen, and Wen-Jing Xiao. "Visible light-driven photocatalytic generation of sulfonamidyl radicals for alkene hydroamination of unsaturated sulfonamides." Chemical Communications 54, no. 50 (2018): 6780–83. http://dx.doi.org/10.1039/c7cc09871e.

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35

Ngo, Thang Ngoc, Peter Ehlers, Tuan Thanh Dang, Alexander Villinger, and Peter Langer. "Synthesis of indolo[1,2-f]phenanthridines by Pd-catalyzed domino C–N coupling/hydroamination/C–H arylation reactions." Organic & Biomolecular Chemistry 13, no. 11 (2015): 3321–30. http://dx.doi.org/10.1039/c5ob00013k.

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36

Hii, King Kuok. "Development of palladium catalysts for asymmetric hydroamination reactions." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 341–49. http://dx.doi.org/10.1351/pac200678020341.

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37

Takagi, Ryukichi, Duyen Thi Duong, and Toshiya Ichiki. "Disulfonimide catalyzed asymmetric intramolecular hydroamination of alkenyl thioureas: Concentration effect in the hydroamination." Tetrahedron 94 (August 2021): 132332. http://dx.doi.org/10.1016/j.tet.2021.132332.

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38

Patil, Nitin T., Pediredla G. V. V. Lakshmi, and Vipender Singh. "ChemInform Abstract: AuI-Catalyzed Direct Hydroamination/Hydroarylation and Double Hydroamination of Terminal Alkynes." ChemInform 41, no. 52 (December 2, 2010): no. http://dx.doi.org/10.1002/chin.201052176.

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39

Chen, Zhuo, Xiao-Di Nie, Jian-Ting Sun, Ai-Mei Yang, and Bang-Guo Wei. "Zn(OTf)2-catalyzed hydroamination of ynamides with aromatic amines." Organic & Biomolecular Chemistry 19, no. 11 (2021): 2492–501. http://dx.doi.org/10.1039/d0ob02603d.

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40

He, Han, Ning Xu, Honglin Zhang, Bin Chen, Zhengnan Hu, Kang Guo, Jianlin Chun, Shujun Cao, and Yingguang Zhu. "Brønsted acid-promoted hydroamination of unsaturated hydrazones: access to biologically important 5-arylpyrazolines." RSC Advances 11, no. 28 (2021): 17340–45. http://dx.doi.org/10.1039/d1ra03043d.

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41

Otero, Antonio, Agustín Lara-Sánchez, José A. Castro-Osma, Isabel Márquez-Segovia, Carlos Alonso-Moreno, Juan Fernández-Baeza, Luis F. Sánchez-Barba, and Ana M. Rodríguez. "Synthesis and structural characterization of amido heteroscorpionate rare-earth metal complexes and hydroamination of aminoalkenes." New Journal of Chemistry 39, no. 10 (2015): 7672–81. http://dx.doi.org/10.1039/c5nj00930h.

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42

Oshimoto, Kohei, Hiroaki Tsuji, and Motoi Kawatsura. "Synthesis of benzoxazoles via the copper-catalyzed hydroamination of alkynones with 2-aminophenols." Organic & Biomolecular Chemistry 17, no. 17 (2019): 4225–29. http://dx.doi.org/10.1039/c9ob00572b.

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43

Trifonov, A. A., I. V. Basalov, and A. A. Kissel. "Use of organolanthanides in the catalytic intermolecular hydrophosphination and hydroamination of multiple C–C bonds." Dalton Transactions 45, no. 48 (2016): 19172–93. http://dx.doi.org/10.1039/c6dt03913h.

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44

Chen, Junqi, Sarah K. Goforth, Bradley A. McKeown, and T. Brent Gunnoe. "Brønsted acid-catalysed intramolecular hydroamination of unactivated alkenes: metal triflates as an in situ source of triflic acid." Dalton Transactions 46, no. 9 (2017): 2884–91. http://dx.doi.org/10.1039/c6dt04710f.

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45

Bawari, Deependra, Bhupendra Goswami, Sabari V. R, Sandeep Kumar Thakur, R. V. Varun Tej, Angshuman Roy Choudhury, and Sanjay Singh. "Neutral and cationic cyclic (alkyl)(amino)carbene mercury [cAAC–Hg(ii)] complexes: scope of hydroamination of alkynes with organomercury compounds." Dalton Transactions 47, no. 18 (2018): 6274–78. http://dx.doi.org/10.1039/c7dt04589a.

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46

Normand, Adrien T., Alexandre Massard, Philippe Richard, Coline Canovas, Cédric Balan, Michel Picquet, Audrey Auffrant, and Pierre Le Gendre. "Titanium imido complexes stabilised by bis(iminophosphoranyl)methanide ligands: the influence of N-substituents on solution dynamics and reactivity." Dalton Trans. 43, no. 40 (2014): 15098–110. http://dx.doi.org/10.1039/c4dt00746h.

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47

Peng, Xingao, Atsushi Kaga, Hajime Hirao, and Shunsuke Chiba. "Hydroamination of alkenyl N-arylhydrazones mediated by t-BuOK for the synthesis of nitrogen heterocycles." Organic Chemistry Frontiers 3, no. 5 (2016): 609–13. http://dx.doi.org/10.1039/c6qo00053c.

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48

Sha, Fanrui, Emily A. Shimizu, Hannah S. Slocumb, Sydney E. Towell, Yi Zhen, Hanna Z. Porter, Michael K. Takase, and Adam R. Johnson. "Catalytic intramolecular hydroamination of aminoallenes using titanium and tantalum complexes of sterically encumbered chiral sulfonamides." Dalton Transactions 49, no. 35 (2020): 12418–31. http://dx.doi.org/10.1039/d0dt02557g.

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49

Nakamura, Yushi, Tetsuo Ohta, and Yohei Oe. "A formal anti-Markovnikov hydroamination of allylic alcohols via tandem oxidation/1,4-conjugate addition/1,2-reduction using a Ru catalyst." Chemical Communications 51, no. 35 (2015): 7459–62. http://dx.doi.org/10.1039/c5cc01584g.

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50

Sun, Qiu, Yaorong Wang, Dan Yuan, Yingming Yao, and Qi Shen. "Zirconium catalysed intermolecular hydroamination reactions of secondary amines with alkynes." Chemical Communications 51, no. 36 (2015): 7633–36. http://dx.doi.org/10.1039/c5cc01780g.

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