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Journal articles on the topic 'Intramolecular hydroamination'

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Author: Grafiati

Published: 4 June 2021

Last updated: 10 March 2023

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1

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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2

Crimmin, Mark R., Ian J. Casely, and Michael S. Hill. "Calcium-Mediated Intramolecular Hydroamination Catalysis." Journal of the American Chemical Society 127, no. 7 (February 2005): 2042–43. http://dx.doi.org/10.1021/ja043576n.

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3

Roesky, P., S. Blechert, A. Zulys, M. Dochnahl, D. Hollmann, K. Löhnwitz, and J. S. Herrmann. "Intramolecular Hydroamination Route to Heterocycles." Synfacts 2006, no. 5 (May 2006): 0438. http://dx.doi.org/10.1055/s-2006-934360.

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4

Zhang, Wen, Jenny B. Werness, and Weiping Tang. "Intramolecular hydroamination of conjugated enynes." Tetrahedron 65, no. 16 (April 2009): 3090–95. http://dx.doi.org/10.1016/j.tet.2008.09.045.

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5

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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6

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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7

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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8

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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9

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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10

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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11

Liu, Yuan, Abosede Adejoke Ogunlana, and Xiaoguang Bao. "Mechanistic insights into Pd(0)-catalyzed intermolecular and intramolecular hydroamination of methylenecyclopropanes: a computational study." Dalton Transactions 47, no. 16 (2018): 5660–69. http://dx.doi.org/10.1039/c8dt00131f.

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12

Siewert, Jan-Erik, André Schumann, Malte Fischer, Christoph Schmidt, Tobias Taeufer, and Christian Hering-Junghans. "Terphenyl(bisamino)phosphines: electron-rich ligands for gold-catalysis." Dalton Transactions 49, no. 35 (2020): 12354–64. http://dx.doi.org/10.1039/d0dt02435j.

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13

Tan, Tong-De, Yang-Bo Chen, Ming-Yang Yang, Jia-Le Wang, Hao-Ze Su, Feng-Lin Hong, Jin-Mei Zhou, and Long-Wu Ye. "Stereoselective synthesis of 2,5-disubstituted pyrrolidines via gold-catalysed anti-Markovnikov hydroamination-initiated tandem reactions." Chemical Communications 55, no. 67 (2019): 9923–26. http://dx.doi.org/10.1039/c9cc05295j.

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14

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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15

Chai, Zhuo, Jiang Chu, Yunyi Qi, Mujun Tang, Jinsong Hou, and Gaosheng Yang. "Half-sandwich chiral rare-earth metal complexes with linked tridentate amido-indenyl ligand: synthesis, characterization, and catalytic properties for intramolecular hydroamination." RSC Advances 7, no. 3 (2017): 1759–65. http://dx.doi.org/10.1039/c6ra26537e.

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16

Koller, Jürgen, and Robert G. Bergman. "Aluminium-catalyzed intramolecular hydroamination of aminoalkenes." Chemical Communications 46, no. 25 (2010): 4577. http://dx.doi.org/10.1039/c002760j.

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17

Kondo, Teruyuki, Takumi Okada, Toshiaki Suzuki, and Take-aki Mitsudo. "Ruthenium-catalyzed intramolecular hydroamination of aminoalkynes." Journal of Organometallic Chemistry 622, no. 1-2 (March 2001): 149–54. http://dx.doi.org/10.1016/s0022-328x(00)00869-x.

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18

Ogata, Tokutaro, Atsushi Ujihara, Susumu Tsuchida, Tomoko Shimizu, Atsunori Kaneshige, and Kiyoshi Tomioka. "Catalytic asymmetric intramolecular hydroamination of aminoalkenes." Tetrahedron Letters 48, no. 38 (September 2007): 6648–50. http://dx.doi.org/10.1016/j.tetlet.2007.07.117.

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19

Hartwig, J., and A. Takemiya. "Syn-Selective anti-Markovnikov Intramolecular Hydroamination." Synfacts 2006, no. 8 (August 2006): 0797. http://dx.doi.org/10.1055/s-2006-941951.

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20

Zhang, Dexing, Ruiting Liu, and Xigeng Zhou. "Intramolecular alkene hydroamination and degradation of amidines: divergent behavior of rare earth metal amidinate intermediates." Catalysis Science & Technology 8, no. 21 (2018): 5573–81. http://dx.doi.org/10.1039/c8cy01481g.

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21

Zhang, Yu, Qiu Sun, Yaorong Wang, Dan Yuan, Yingming Yao, and Qi Shen. "Intramolecular hydroamination reactions catalyzed by zirconium complexes bearing bridged bis(phenolato) ligands." RSC Advances 6, no. 13 (2016): 10541–48. http://dx.doi.org/10.1039/c5ra23270h.

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Cationic species derived from zirconium complexes stabilized by bridged bis(phenolato) ligands showed good activities in catalyzing intramolecular hydroamination/cyclization of primary and secondary amines.

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22

Wang, Liqun, Kangqi Shen, Mingyang Chen, and Yan Zhu. "One-core-atom loss in a gold nanocluster promotes hydroamination reaction of alkynes." Nanoscale 11, no. 29 (2019): 13767–72. http://dx.doi.org/10.1039/c9nr04219a.

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23

Mahdavi, Mohammad, Rasoul Hassanzadeh-Soureshjan, Mina Saeedi, Alireza Ariafard, Rasool BabaAhmadi, Parviz Rashidi Ranjbar, and Abbas Shafiee. "Experimental and computational evidence for KOt-Bu-promoted synthesis of oxopyrazino[1,2-a]indoles." RSC Advances 5, no. 123 (2015): 101353–61. http://dx.doi.org/10.1039/c5ra17056g.

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24

Shen, Yi, Scott M. Shepard, Christopher J. Reed, and Paula L. Diaconescu. "Zirconium complexes supported by a ferrocene-based ligand as redox switches for hydroamination reactions." Chemical Communications 55, no. 39 (2019): 5587–90. http://dx.doi.org/10.1039/c9cc01076a.

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25

Sun, Yuan-Ming, Peng Gu, Yu-Ning Gao, Qin Xu, and Min Shi. "Gold(i) catalyzed tandem cyclization of propargylic esters to 4-acyloxy-1,2-dihydroquinolines." Chemical Communications 52, no. 42 (2016): 6942–45. http://dx.doi.org/10.1039/c6cc03132c.

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Gold catalyzed tandem [3,3]-rearrangement and intramolecular hydroamination of propargylic esters has been disclosed in this communication, producing a series of 4-acyloxy-1,2-dihydroquinolines in good yields and high enantioselectivities.

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26

Li, Sifeng, Zihao Wang, Haitao Xiao, Zhaoxiang Bian, and Jun (Joelle) Wang. "Enantioselective synthesis of indole derivatives by Rh/Pd relay catalysis and their anti-inflammatory evaluation." Chemical Communications 56, no. 55 (2020): 7573–76. http://dx.doi.org/10.1039/d0cc03158e.

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An efficient Rh/Pd relay catalyzed intermolecular and cascade intramolecular hydroamination for the synthesis of exclusive trans 1-indolyl dihydronaphthalenols (up to 88% yield, 99% ee) is described under mild conditions.

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27

Ngo, Thang Ngoc, Frank Janert, Peter Ehlers, Do Huy Hoang, Tuan Thanh Dang, Alexander Villinger, Stefan Lochbrunner, and Peter Langer. "Pd(0)-catalyzed domino C–N coupling/hydroamination/C–H arylation reactions: efficient synthesis and photophysical properties of azaindolo[1,2-f]phenanthridines." Organic & Biomolecular Chemistry 14, no. 4 (2016): 1293–301. http://dx.doi.org/10.1039/c5ob02274f.

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A series of new 7- and 4-azaindolo[1,2-f]phenanthridines were synthesized by a domino Pd(0)-catalyzed reaction, which involves three sequential steps: C–N coupling, hydroamination, and intramolecular C–H arylation.

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28

Chou, Ting-Hung, Bo-Hung Yu, and Rong-Jie Chein. "ZnI2/Zn(OTf)2-TsOH: a versatile combined-acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization." Chemical Communications 55, no. 90 (2019): 13522–25. http://dx.doi.org/10.1039/c9cc07242j.

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A mild and efficient combined-acid system using a zinc(ii) salt [ZnI₂ or Zn(OTf)₂] and TsOH was investigated for intramolecular hydrocarboxylation, hydroalkoxylation, hydroamination, hydroamidation, and hydroarylation and polyene cyclizations.

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29

Knight, David, Thomas Wirth, and Abdul Hadi Aldmairi. "Morpholin-2-one Derivatives via Intramolecular Acid-Catalyzed Hydroamination." Synthesis 51, no. 07 (January 7, 2019): 1643–48. http://dx.doi.org/10.1055/s-0037-1610674.

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Substituted morpholin-2-one derivatives were readily obtained in two steps starting from commercially available N-protected amino acids. In a metal-free and practical method, a catalytic amount of trifluoromethanesulfonic acid was sufficient to generate morpholinones under mild reaction conditions in an intramolecular hydroamination reaction in good to excellent yields.

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30

Lutete, Léopold M., Isao Kadota, and Yoshinori Yamamoto. "Palladium-Catalyzed Intramolecular Asymmetric Hydroamination of Alkynes." Journal of the American Chemical Society 126, no. 6 (February 2004): 1622–23. http://dx.doi.org/10.1021/ja039774g.

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31

Patton, Duncan A., and Matthew E. Cremeens. "Organometallic catalysts for intramolecular hydroamination of alkenes." Review Journal of Chemistry 4, no. 1 (January 2014): 1–20. http://dx.doi.org/10.1134/s207997801304002x.

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32

Zhang, Wen, Jenny B. Werness, and Weiping Tang. "Base-Catalyzed Intramolecular Hydroamination of Conjugated Enynes." Organic Letters 10, no. 10 (May 2008): 2023–26. http://dx.doi.org/10.1021/ol800334m.

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33

Brown, Adam R., Christopher Uyeda, Carolyn A. Brotherton, and Eric N. Jacobsen. "Enantioselective Thiourea-Catalyzed Intramolecular Cope-Type Hydroamination." Journal of the American Chemical Society 135, no. 18 (April 24, 2013): 6747–49. http://dx.doi.org/10.1021/ja402893z.

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34

Khandelwal, Manish, and Rudolf J. Wehmschulte. "Cationic organoaluminum compounds as intramolecular hydroamination catalysts." Journal of Organometallic Chemistry 696, no. 26 (January 2012): 4179–83. http://dx.doi.org/10.1016/j.jorganchem.2011.09.010.

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35

Li, Yanwu, and Tobin J. Marks. "Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization of Aminoalkynes." Journal of the American Chemical Society 118, no. 39 (January 1996): 9295–306. http://dx.doi.org/10.1021/ja9612413.

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36

Spallek, Tatiana, and Reiner Anwander. "Rare-earth metal diisopropylamide-catalyzed intramolecular hydroamination." Dalton Transactions 45, no. 41 (2016): 16393–403. http://dx.doi.org/10.1039/c6dt03045a.

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37

Arredondo, Victor M., Frank E. McDonald, and Tobin J. Marks. "Organolanthanide-Catalyzed Intramolecular Hydroamination/Cyclization of Aminoallenes." Journal of the American Chemical Society 120, no. 19 (May 1998): 4871–72. http://dx.doi.org/10.1021/ja9743248.

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38

Quinet, Coralie, Laetitia Sampoux, and István E. Markó. "Base-Catalysed Intramolecular Hydroamination of Vinyl Sulfides." European Journal of Organic Chemistry 2009, no. 11 (April 2009): 1806–11. http://dx.doi.org/10.1002/ejoc.200900009.

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39

Berthold, Dino, Arne G. A. Geissler, Sabrina Giofré, and Bernhard Breit. "Rhodium‐Catalyzed Asymmetric Intramolecular Hydroamination of Allenes." Angewandte Chemie International Edition 58, no. 29 (July 15, 2019): 9994–97. http://dx.doi.org/10.1002/anie.201904833.

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40

Berthold, Dino, Arne G. A. Geissler, Sabrina Giofré, and Bernhard Breit. "Rhodium‐Catalyzed Asymmetric Intramolecular Hydroamination of Allenes." Angewandte Chemie 131, no. 29 (June 21, 2019): 10099–102. http://dx.doi.org/10.1002/ange.201904833.

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41

Gaggioli, Carlo Alberto, Gianluca Ciancaleoni, Luca Biasiolo, Giovanni Bistoni, Daniele Zuccaccia, Leonardo Belpassi, Paola Belanzoni, and Francesco Tarantelli. "Anomalous ligand effect in gold(i)-catalyzed intramolecular hydroamination of alkynes." Chemical Communications 51, no. 27 (2015): 5990–93. http://dx.doi.org/10.1039/c5cc00894h.

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42

Yang, Zehua, Chao Xia, Delong Liu, Yangang Liu, Masashi Sugiya, Tsuneo Imamoto, and Wanbin Zhang. "P-stereogenic PNP pincer-Pd catalyzed intramolecular hydroamination of amino-1,3-dienes." Organic & Biomolecular Chemistry 13, no. 9 (2015): 2694–702. http://dx.doi.org/10.1039/c4ob02402h.

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A new P-stereogenic PNP pincer-Pd complex was readily prepared and was used in the asymmetric intramolecular hydroamination of amino-1,3-dienes, with the desired products being obtained in good yields and with excellent regioselectivities and up to moderate enantioselectivities.

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43

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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44

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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45

Tomioka, Kiyoshi, Takeo Sakai, Tokutaro Ogata, and Yasutomo Yamamoto. "Aminolithiation of carbon-carbon double bonds as a powerful tool in organic synthesis." Pure and Applied Chemistry 81, no. 2 (January 1, 2009): 247–53. http://dx.doi.org/10.1351/pac-con-08-08-02.

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A conjugate amination of α,β-unsaturated carbonyl compounds with lithium amides has become a powerful method of N-C bond-forming reactions. Chiral ligand-controlled asymmetric version of the conjugate amination of enoates was developed for practical bench chemistry, giving the enantioenriched amination product with over 99 % ee. In situ diastereoselective alkylation of resulting lithium enolates allowed us to form vicinal N-C and C-C bonds in a one-pot operation. This protocol enabled us to realize a short-step asymmetric synthesis of otamixaban key intermediate. Treatment of product 3-benzylamino- and 3-allylaminoesters with tert-butyllithium gave five- or seven-membered lactams through [1,2]- or [2,3]-rearrangement of intermediate β-lactams. Isolated C-C double bonds were also found to accept intramolecular aminolithiation affording the corresponding hydroamination products. Chiral lithiophilic ligand-catalyzed reaction gave enantioenriched hydroamination products with high ee. Stereoselective intramolecular aminolithiation of allylaminoalkenes was coupled with subsequent carbolithiation to give doubly cyclized product amines.

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46

Shibuya, Masatoshi, Shoji Fujita, and Yoshihiko Yamamoto. "Intramolecular Hydroalkoxylation/Reduction and Hydroamination/Reduction of Unactivated Alkynes Using a Silane–Iodine Catalytic System." Synthesis 49, no. 18 (May 24, 2017): 4199–204. http://dx.doi.org/10.1055/s-0036-1588436.

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A transition-metal-free silane–iodine catalytic system comprising I2 and Et3SiH promotes intramolecular hydroalkoxylation/reduction and hydroamination/reduction of unactivated alkynes. This system allows the reaction to proceed at room temperature affording 2,4- and 2,5-disubstituted pyrrolidines as well as a 2,3-disubstituted tetrahydrofuran with high diastereoselectivity.

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47

LaLonde, Rebecca L., Benjamin D. Sherry, Eun Joo Kang, and F. Dean Toste. "Gold(I)-Catalyzed Enantioselective Intramolecular Hydroamination of Allenes." Journal of the American Chemical Society 129, no. 9 (March 2007): 2452–53. http://dx.doi.org/10.1021/ja068819l.

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48

Majumder, Supriyo, and Aaron L. Odom. "Group-4 Dipyrrolylmethane Complexes in Intramolecular Olefin Hydroamination." Organometallics 27, no. 6 (March 2008): 1174–77. http://dx.doi.org/10.1021/om700883a.

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49

Carney, Jeffrey M., Patrick J. Donoghue, William M. Wuest, Olaf Wiest, and Paul Helquist. "Intramolecular Hydroamination of Aminoalkynes with Silver−Phenanthroline Catalysts." Organic Letters 10, no. 17 (September 4, 2008): 3903–6. http://dx.doi.org/10.1021/ol801458g.

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50

Hannedouche, Jérôme, Jacqueline Collin, Alexander Trifonov, and Emmanuelle Schulz. "Intramolecular enantioselective hydroamination catalyzed by rare earth binaphthylamides." Journal of Organometallic Chemistry 696, no. 1 (January 2011): 255–62. http://dx.doi.org/10.1016/j.jorganchem.2010.09.013.

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