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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, David Portehault, Corinne Chanéac, Clément Sanchez, Philippe Marcus, François Ribot, Louis Fensterbank, and Sophie Carenco. "Direct Synthesis of N‐Heterocyclic Carbene‐Stabilized Copper Nanoparticles from an N‐Heterocyclic Carbene–Borane." Chemistry – A European Journal 25, no. 49 (August 5, 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 (January 18, 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 (January 4, 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 H₂ 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 (November 21, 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 (January 22, 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, Hélène Bonin-Dubarle, Dennis P. Curran, Max Malacria, Louis Fensterbank, Emmanuel Lacôte, Jacques Lalevée, and Jean-Pierre Fouassier. "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, Emmanuel Lacôte, Max Malacria, Qianli Chu, Shau-Hua Ueng, Andrey Solovyev, and Dennis P. Curran. "EPR Studies of the Generation, Structure, and Reactivity of N-Heterocyclic Carbene Borane Radicals." Journal of the American Chemical Society 132, no. 7 (February 24, 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 (January 18, 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, Jia-Qiang Wu, Zhi-Shu Huang, Qingjiang Li, and Honggen Wang. "Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes." Organic Letters 23, no. 5 (February 16, 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 (July 24, 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 deactivation pathway was found in the case of NHC-Al(III) hydrides.

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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 (September 27, 2010): 4004–6. http://dx.doi.org/10.1021/om100747j.

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18

Solovyev, Andrey, Shau-Hua Ueng, Julien Monot, Louis Fensterbank, Max Malacria, Emmanuel Lacôte, and Dennis P. Curran. "Estimated Rate Constants for Hydrogen Abstraction from N-Heterocyclic Carbene−Borane Complexes by an Alkyl Radical†." Organic Letters 12, no. 13 (July 2, 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, Yubin Yim, Hyuk Kang, Hwan Myung Kim, Jean Bouffard, and Juyoung Yoon. "Endoplasmic Reticulum-Targeted Ratiometric N-Heterocyclic Carbene Borane Probe for Two-Photon Microscopic Imaging of Hypochlorous Acid." Analytical Chemistry 90, no. 21 (October 10, 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 (January 14, 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 (June 24, 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 (November 8, 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 (April 25, 2013): no. http://dx.doi.org/10.1002/chin.201320044.

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25

Deev, Sergey, Sviatoslav Batsyts, Ekaterina Sheina, Tatyana S. Shestakova, Igor Khalimbadzha, Mikhail A. Kiskin, Valery Charushin, 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 (January 20, 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 (October 10, 2013): 6209–17. http://dx.doi.org/10.1021/om400800d.

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27

Takahashi, Kosuke, Masaki Shimoi, Takashi Watanabe, Katsuhiro Maeda, Steven J. Geib, Dennis P. Curran, and Tsuyoshi Taniguchi. "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 (February 25, 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 (March 9, 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 (March 9, 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 (November 27, 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 (July 29, 2010): no. http://dx.doi.org/10.1002/chin.201034071.

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33

Aubry, Bérengère, Daniel Subervie, Muriel Lansalot, Elodie Bourgeat-Lami, Bernadette Graff, Fabrice Morlet-Savary, Céline Dietlin, Jean-Pierre Fouassier, Emmanuel Lacôte, and Jacques Lalevée. "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 (November 26, 2018): 9730–39. http://dx.doi.org/10.1021/acs.macromol.8b01669.

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34

Cesari, Cristiana, Beatrice Berti, Francesco Calcagno, Carlo Lucarelli, Marco Garavelli, Rita Mazzoni, Ivan Rivalta, and Stefano Zacchini. "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 (July 30, 2021): 2724–35. http://dx.doi.org/10.1021/acs.organomet.1c00363.

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35

Holschumacher, Dirk, Thomas Bannenberg, Cristian G Hrib, Peter G Jones, Matthias Tamm, Preston A Chase, and Douglas W Stephan. "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 (September 15, 2008): 7479. http://dx.doi.org/10.1002/ange.200890244.

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36

Holschumacher, Dirk, Thomas Bannenberg, Cristian G Hrib, Peter G Jones, Matthias Tamm, Preston A Chase, and Douglas W Stephan. "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 (September 15, 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 (December 24, 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 (June 22, 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 (October 24, 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 (October 24, 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 (September 7, 2011): 10294–317. http://dx.doi.org/10.1002/anie.201102717.

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45

Horn, Markus, Herbert Mayr, Emmanuel Lacôte, Everett Merling, Jordan Deaner, Sarah Wells, Timothy McFadden, and Dennis P. Curran. "N-Heterocyclic Carbene Boranes are Good Hydride Donors." Organic Letters 14, no. 1 (December 13, 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, and 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, no. 31 (July 11, 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 (July 31, 2013): 12076–81. http://dx.doi.org/10.1021/ja4056245.

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49

Chu, Qianli, Malika MakhloufâBrahmi, Andrey Solovyev, Shau-Hua Ueng, DennisâP Curran, Max Malacria, Louis Fensterbank, and Emmanuel LacÃ´te. "Ionic and Organometallic Reductions with N-Heterocyclic Carbene Boranes." Chemistry - A European Journal 15, no. 47 (December 7, 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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