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Journal articles on the topic 'Carbene N-Heterocyclic borane'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

Frogneux, Xavier, Laura Hippolyte, Dimitri Mercier, et al. "Direct Synthesis of N‐Heterocyclic Carbene‐Stabilized Copper Nanoparticles from an N‐Heterocyclic Carbene–Borane." Chemistry – A European Journal 25, no. 49 (2019): 11481–85. http://dx.doi.org/10.1002/chem.201901534.

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2

Pidlypnyi, Nazar, Jan C. Namyslo, Martin H. H. Drafz, Martin Nieger, and Andreas Schmidt. "Betaine–Carbene Interconversions. From N-Ylides to Zwitterionic N-Heterocyclic Carbene–Borane Adducts." Journal of Organic Chemistry 78, no. 3 (2013): 1070–79. http://dx.doi.org/10.1021/jo302479p.

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3

Winkler, Andrea, Matthias Freytag, Peter G. Jones, and Matthias Tamm. "Preparation and reactivity of an isolable N-heterocyclic carbene–borane." Journal of Organometallic Chemistry 775 (January 2015): 164–68. http://dx.doi.org/10.1016/j.jorganchem.2014.04.037.

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4

Banerjee, Dipshikha, Céline Besnard, and E. Peter Kündig. "Chiral N-Heterocyclic Carbene Borane Complexes: Synthesis and Structural Analysis." Organometallics 31, no. 2 (2012): 709–15. http://dx.doi.org/10.1021/om201087n.

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5

Korytiaková, Eva, Niklas O. Thiel, Felix Pape, and Johannes F. Teichert. "Copper(i)-catalysed transfer hydrogenations with ammonia borane." Chemical Communications 53, no. 4 (2017): 732–35. http://dx.doi.org/10.1039/c6cc09067b.

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Highly Z-selective alkyne transfer semihydrogenations and conjugate transfer hydrogenations of enoates can be effected by employing a readily available copper(i)/N-heterocyclic carbene (NHC) complex, [IPrCuOH], in combination with ammonia borane as a H<sub>2</sub> equivalent.

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6

Liu, Ming, Jan C. Namyslo, Martin Nieger, Mika Polamo, and Andreas Schmidt. "From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer." Beilstein Journal of Organic Chemistry 12 (December 8, 2016): 2673–81. http://dx.doi.org/10.3762/bjoc.12.264.

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The mesomeric betaine imidazolium-1-ylphenolate forms a borane adduct with tris(pentafluorophenyl)borane by coordination with the phenolate oxygen, whereas its NHC tautomer 1-(2-phenol)imidazol-2-ylidene reacts with (triphenylphosphine)gold(I) chloride to give the cationic NHC complex [Au(NHC)2][Cl] by coordination with the carbene carbon atom. The anionic N-heterocyclic carbene 1-(2-phenolate)imidazol-2-ylidene gives the complexes [K][Au(NHC−)2], [Rh(NHC−)3] and [Ni(NHC−)2], respectively. Results of four single crystal analyses are presented.

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7

Lamm, Vladimir, Xiangcheng Pan, Tsuyoshi Taniguchi, and Dennis P. Curran. "Reductions of aldehydes and ketones with a readily available N-heterocyclic carbene borane and acetic acid." Beilstein Journal of Organic Chemistry 9 (April 8, 2013): 675–80. http://dx.doi.org/10.3762/bjoc.9.76.

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Acetic acid promotes the reduction of aldehydes and ketones by the readily available N-heterocyclic carbene borane, 1,3-dimethylimidazol-2-ylidene borane. Aldehydes are reduced over 1–24 h at room temperature with 1 equiv of acetic acid and 0.5 equiv of the NHC-borane. Ketone reductions are slower but can be accelerated by using 5 equiv of acetic acid. Aldehydes can be selectively reduced in the presence of ketones. On a small scale, products are isolated by evaporation of the reaction mixture and direct chromatography.

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8

Bolt, Daniel A., and Dennis P. Curran. "1-Butyl-3-methylimidazol-2-ylidene Borane: A Readily Available, Liquid N-Heterocyclic Carbene Borane Reagent." Journal of Organic Chemistry 82, no. 24 (2017): 13746–50. http://dx.doi.org/10.1021/acs.joc.7b02730.

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9

Takahashi, Kosuke, Steven J. Geib, Katsuhiro Maeda, Dennis P. Curran, and Tsuyoshi Taniguchi. "Radical trans-Hydroboration of Substituted 1,3-Diynes with an N-Heterocyclic Carbene Borane." Organic Letters 23, no. 3 (2021): 1071–75. http://dx.doi.org/10.1021/acs.orglett.0c04284.

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10

Zhang, Jiaxi, Eike G. Hübner, Jan C. Namyslo, Martin Nieger, and Andreas Schmidt. "Purine-substituted imidazolium mesomeric betaines and their tautomeric N-heterocyclic carbenes. Formation of a cyclic borane adduct." Organic & Biomolecular Chemistry 16, no. 36 (2018): 6801–8. http://dx.doi.org/10.1039/c8ob01916a.

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11

Tehfe, Mohamad-Ali, Julien Monot, Malika Makhlouf Brahmi, et al. "N-Heterocyclic carbene-borane radicals as efficient initiating species of photopolymerization reactions under air." Polym. Chem. 2, no. 3 (2011): 625–31. http://dx.doi.org/10.1039/c0py00296h.

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12

Walton, John C., Malika Makhlouf Brahmi, Louis Fensterbank, et al. "EPR Studies of the Generation, Structure, and Reactivity of N-Heterocyclic Carbene Borane Radicals." Journal of the American Chemical Society 132, no. 7 (2010): 2350–58. http://dx.doi.org/10.1021/ja909502q.

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13

Wang, Yuzhong, Mariham Y. Abraham, Robert J. Gilliard, Pingrong Wei, Jared C. Smith, and Gregory H. Robinson. "From Anionic N-Heterocyclic Dicarbenes to Abnormal Carbene–Borane Complexes: A Logical Synthetic Route." Organometallics 31, no. 3 (2012): 791–93. http://dx.doi.org/10.1021/om201259d.

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14

Liu, Ming, Martin Nieger, and Andreas Schmidt. "Mesomeric betaine – N-heterocyclic carbene interconversions of 1,2,4-triazolium-phenolates. Sulfur, selenium, and borane adduct formation." Chemical Communications 51, no. 3 (2015): 477–79. http://dx.doi.org/10.1039/c4cc08032g.

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15

Liu, Yao, Ji-Lin Li, Xu-Ge Liu, et al. "Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes." Organic Letters 23, no. 5 (2021): 1891–97. http://dx.doi.org/10.1021/acs.orglett.1c00309.

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16

Weetman, Catherine, Nozomi Ito, Masafumi Unno, Franziska Hanusch, and Shigeyoshi Inoue. "NHI- and NHC-Supported Al(III) Hydrides for Amine–Borane Dehydrocoupling Catalysis." Inorganics 7, no. 8 (2019): 92. http://dx.doi.org/10.3390/inorganics7080092.

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The catalytic dehydrocoupling of amine–boranes has recently received a great deal of attention due to its potential in hydrogen storage applications. The use of aluminum catalysts for this transformation would provide an additional cost-effective and sustainable approach towards the hydrogen economy. Herein, we report the use of both N-heterocyclic imine (NHI)- and carbene (NHC)-supported Al(III) hydrides and their role in the catalytic dehydrocoupling of Me2NHBH3. Differences in the σ-donating ability of the ligand class resulted in a more stable catalyst for NHI-Al(III) hydrides, whereas a d

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17

Tsai, Jie-Hong, Shen-Ta Lin, Richard Bing-Gong Yang, Glenn P. A. Yap, and Tiow-Gan Ong. "Two-Way Street Transformation of Boronium and Borane Complexes Facilitated by Amino-Linked N-Heterocyclic Carbene." Organometallics 29, no. 18 (2010): 4004–6. http://dx.doi.org/10.1021/om100747j.

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18

Solovyev, Andrey, Shau-Hua Ueng, Julien Monot, et al. "Estimated Rate Constants for Hydrogen Abstraction from N-Heterocyclic Carbene−Borane Complexes by an Alkyl Radical†." Organic Letters 12, no. 13 (2010): 2998–3001. http://dx.doi.org/10.1021/ol101014q.

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19

Hartmann, Caroline E., Václav Jurčík, Olivier Songis, and Catherine S. J. Cazin. "Tandem ammonia borane dehydrogenation/alkene hydrogenation mediated by [Pd(NHC)(PR3)] (NHC = N-heterocyclic carbene) catalysts." Chem. Commun. 49, no. 10 (2013): 1005–7. http://dx.doi.org/10.1039/c2cc38145a.

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20

Pak, Yen Leng, Sang Jun Park, Gyeongok Song, et al. "Endoplasmic Reticulum-Targeted Ratiometric N-Heterocyclic Carbene Borane Probe for Two-Photon Microscopic Imaging of Hypochlorous Acid." Analytical Chemistry 90, no. 21 (2018): 12937–43. http://dx.doi.org/10.1021/acs.analchem.8b03565.

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21

Li, Yufei, Soren K. Mellerup, Francoise Sauriol, Gabriele Schatte, and Suning Wang. "Unusual Fragmentation and Transformation of an N-Heterocyclic Carbene by a Stable Phosphonium-Borane peri -Functionalized Naphthalene." Chemistry - A European Journal 22, no. 7 (2016): 2473–80. http://dx.doi.org/10.1002/chem.201504156.

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22

Nelson, David J., Byron J. Truscott, Jonathan D. Egbert, and Steven P. Nolan. "Exploring the Limits of Catalytic Ammonia–Borane Dehydrogenation Using a Bis(N-heterocyclic carbene) Iridium(III) Complex." Organometallics 32, no. 13 (2013): 3769–72. http://dx.doi.org/10.1021/om400402r.

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23

Boussonnière, Anne, Xiangcheng Pan, Steven J. Geib, and Dennis P. Curran. "Borenium-Catalyzed Hydroborations of Silyl-Substituted Alkenes and Alkynes with a Readily Available N-Heterocyclic Carbene–Borane." Organometallics 32, no. 24 (2013): 7445–50. http://dx.doi.org/10.1021/om400932g.

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24

Hartmann, Caroline E., Vaclav Jurcik, Olivier Songis, and Catherine S. J. Cazin. "ChemInform Abstract: Tandem Ammonia Borane Dehydrogenation/Alkene Hydrogenation Mediated by [Pd(NHC)(PR3)] (NHC = N-Heterocyclic Carbene) Catalysts." ChemInform 44, no. 20 (2013): no. http://dx.doi.org/10.1002/chin.201320044.

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25

Deev, Sergey, Sviatoslav Batsyts, Ekaterina Sheina, et al. "Betaine-N-Heterocyclic Carbene Interconversions of Quinazolin-4-One Imidazolium Mesomeric Betaines. Sulfur, Selenium, and Borane Adduct Formation." European Journal of Organic Chemistry 2020, no. 4 (2020): 450–65. http://dx.doi.org/10.1002/ejoc.201901622.

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26

Iversen, Kalon J., David J. D. Wilson, and Jason L. Dutton. "Comparison of the Mechanism of Borane, Silane, and Beryllium Hydride Ring Insertion into N-Heterocyclic Carbene C–N Bonds: A Computational Study." Organometallics 32, no. 21 (2013): 6209–17. http://dx.doi.org/10.1021/om400800d.

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27

Takahashi, Kosuke, Masaki Shimoi, Takashi Watanabe, et al. "Revisiting Polyfluoroarenes as Radical Acceptors: Radical C–F Bond Borylation of Polyfluoroarenes with N-Heterocyclic Carbene Boranes and Synthesis of Borane-Containing Liquid Crystals." Organic Letters 22, no. 5 (2020): 2054–59. http://dx.doi.org/10.1021/acs.orglett.0c00481.

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28

Lindsay, David M., and David McArthur. "The synthesis of chiral N-heterocyclic carbene–borane and –diorganoborane complexes and their use in the asymmetric reduction of ketones." Chemical Communications 46, no. 14 (2010): 2474. http://dx.doi.org/10.1039/c001466d.

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29

Zimmerman, Paul M, Ankan Paul, Zhiyong Zhang, and Charles B Musgrave. "The Role of Free N-Heterocyclic Carbene (NHC) in the Catalytic Dehydrogenation of Ammonia-Borane in the Nickel NHC System." Angewandte Chemie 121, no. 12 (2009): 2235–39. http://dx.doi.org/10.1002/ange.200803211.

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30

Zimmerman, Paul M, Ankan Paul, Zhiyong Zhang, and Charles B Musgrave. "The Role of Free N-Heterocyclic Carbene (NHC) in the Catalytic Dehydrogenation of Ammonia-Borane in the Nickel NHC System." Angewandte Chemie International Edition 48, no. 12 (2009): 2201–5. http://dx.doi.org/10.1002/anie.200803211.

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31

Pan, Xiangcheng, Jacques Lalevée, Emmanuel Lacôte, and Dennis P. Curran. "Disulfides and Boryl Sulfides Serve as both Initiators and Precatalysts in Radical Reductions of Halides by an N‐Heterocyclic Carbene⋅Borane." Advanced Synthesis & Catalysis 355, no. 18 (2013): 3522–26. http://dx.doi.org/10.1002/adsc.201300752.

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32

Lindsay, David M., and David McArthur. "ChemInform Abstract: The Synthesis of Chiral N-Heterocyclic Carbene-Borane and -Diorganoborane Complexes and Their Use in the Asymmetric Reduction of Ketones." ChemInform 41, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.201034071.

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33

Aubry, Bérengère, Daniel Subervie, Muriel Lansalot, et al. "A Second-Generation Chameleon N-Heterocyclic Carbene–Borane Coinitiator for the Visible-Light Oxygen-Resistant Photopolymerization of Both Organic and Water-Compatible Resins." Macromolecules 51, no. 23 (2018): 9730–39. http://dx.doi.org/10.1021/acs.macromol.8b01669.

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34

Cesari, Cristiana, Beatrice Berti, Francesco Calcagno, et al. "Bimetallic Co–M (M = Cu, Ag, and Au) Carbonyl Complexes Supported by N-Heterocyclic Carbene Ligands: Synthesis, Structures, Computational Investigation, and Catalysis for Ammonia Borane Dehydrogenation." Organometallics 40, no. 15 (2021): 2724–35. http://dx.doi.org/10.1021/acs.organomet.1c00363.

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35

Holschumacher, Dirk, Thomas Bannenberg, Cristian G Hrib, et al. "Titelbild: Heterolytic Dihydrogen Activation by a Frustrated Carbene-Borane Lewis Pair / Hydrogen and Amine Activation by a Frustrated Lewis Pair of a Bulky N-Heterocyclic Carbene and B(C6F5)3(Angew. Chem. 39/2008)." Angewandte Chemie 120, no. 39 (2008): 7479. http://dx.doi.org/10.1002/ange.200890244.

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36

Holschumacher, Dirk, Thomas Bannenberg, Cristian G Hrib, et al. "Cover Picture: Heterolytic Dihydrogen Activation by a Frustrated Carbene-Borane Lewis Pair / Hydrogen and Amine Activation by a Frustrated Lewis Pair of a Bulky N-Heterocyclic Carbene and B(C6F5)3(Angew. Chem. Int. Ed. 39/2008)." Angewandte Chemie International Edition 47, no. 39 (2008): 7369. http://dx.doi.org/10.1002/anie.200890190.

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37

Ono, Shintaro, Takashi Watanabe, Yosuke Nakamura, Hiroyasu Sato, Toru Hashimoto, and Yoshitaka Yamaguchi. "Synthesis of N -heterocyclic carbene boranes via silver N -heterocyclic carbene complexes." Polyhedron 137 (November 2017): 296–305. http://dx.doi.org/10.1016/j.poly.2017.08.045.

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38

Wang, Xue, Yu-jie Yang, Yan-di Song, Shuang Zhao, and Hong-jie Qu. "Research Progress on N-heterocyclic Carbene Boranes." Scholars International Journal of Chemistry and Material Sciences 3, no. 10 (2020): 152–63. http://dx.doi.org/10.36348/sijcms.2020.v03i10.002.

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39

Allen, Thomas H., Takuji Kawamoto, Sean Gardner, Steven J. Geib, and Dennis P. Curran. "N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters." Organic Letters 19, no. 13 (2017): 3680–83. http://dx.doi.org/10.1021/acs.orglett.7b01777.

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40

Kim, Youngsuk, and Eunsung Lee. "An air-stable N-heterocyclic carbene iminoxyl borate radical zwitterion." Chemical Communications 54, no. 50 (2018): 6824–27. http://dx.doi.org/10.1039/c8cc01399c.

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41

Zhang, Jiaxi, Nazar Pidlypnyi, Martin Nieger, Jan C. Namyslo, and Andreas Schmidt. "Zwitterionic borane adducts of N-heterocyclic carbenes from mesomeric betaines of uracil." Org. Biomol. Chem. 12, no. 17 (2014): 2737–44. http://dx.doi.org/10.1039/c3ob42462f.

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42

Taniguchi, Tsuyoshi, and Dennis P. Curran. "Hydroboration of Arynes with N-Heterocyclic Carbene Boranes." Angewandte Chemie 126, no. 48 (2014): 13366–70. http://dx.doi.org/10.1002/ange.201408345.

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43

Taniguchi, Tsuyoshi, and Dennis P. Curran. "Hydroboration of Arynes with N-Heterocyclic Carbene Boranes." Angewandte Chemie International Edition 53, no. 48 (2014): 13150–54. http://dx.doi.org/10.1002/anie.201408345.

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44

Curran, Dennis P., Andrey Solovyev, Malika Makhlouf Brahmi, Louis Fensterbank, Max Malacria, and Emmanuel Lacôte. "Synthesis and Reactions of N-Heterocyclic Carbene Boranes." Angewandte Chemie International Edition 50, no. 44 (2011): 10294–317. http://dx.doi.org/10.1002/anie.201102717.

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45

Horn, Markus, Herbert Mayr, Emmanuel Lacôte, et al. "N-Heterocyclic Carbene Boranes are Good Hydride Donors." Organic Letters 14, no. 1 (2011): 82–85. http://dx.doi.org/10.1021/ol202836p.

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46

Iversen, Kalon J., David J. D. Wilson, and Jason L. Dutton. "Effects of the electronic structure of five-membered N-heterocyclic carbenes on insertion of silanes and boranes into the NHC C–N bond." Dalton Transactions 44, no. 7 (2015): 3318–25. http://dx.doi.org/10.1039/c4dt03566f.

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47

Dai, Wen, Steven J. Geib та Dennis P. Curran. "Facile Synthesis of α-N-Heterocyclic Carbene-Boryl Ketones from N-Heterocyclic Carbene-Boranes and Alkenyl Triflates". Journal of the American Chemical Society 141, № 31 (2019): 12355–61. http://dx.doi.org/10.1021/jacs.9b05547.

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48

Li, Xiben, and Dennis P. Curran. "Insertion of Reactive Rhodium Carbenes into Boron–Hydrogen Bonds of Stable N-Heterocyclic Carbene Boranes." Journal of the American Chemical Society 135, no. 32 (2013): 12076–81. http://dx.doi.org/10.1021/ja4056245.

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49

Chu, Qianli, Malika MakhloufâBrahmi, Andrey Solovyev, et al. "Ionic and Organometallic Reductions with N-Heterocyclic Carbene Boranes." Chemistry - A European Journal 15, no. 47 (2009): 12937–40. http://dx.doi.org/10.1002/chem.200902450.

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50

Liu, Yuan-Zhong, Jing Wang, Yue Zhao, Lei Chen, Xue-Tai Chen, and Zi-Ling Xue. "Four-coordinate Co(ii) and Fe(ii) complexes with bis(N-heterocyclic carbene)borate and their magnetic properties." Dalton Transactions 44, no. 3 (2015): 908–11. http://dx.doi.org/10.1039/c4dt02537g.

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Both square planar and tetrahedral isomers of the four-coordinate Co(ii) complex with a bis(N-heterocyclic carbene)borate ligand were isolated while only a tetrahedral configuration was found for the Fe(ii) analogue.

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