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Journal articles on the topic 'NHC-borane'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 May 2024

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1

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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2

Tröger-Müller, Steffen, Markus Antonietti, and Clemens Liedel. "Stability of the zwitterionic liquid butyl-methyl-imidazol-2-ylidene borane." Physical Chemistry Chemical Physics 20, no. 16 (2018): 11437–43. http://dx.doi.org/10.1039/c8cp00311d.

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3

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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4

Holschumacher, Dirk, Constantin G. Daniliuc, Peter G. Jones, and Matthias Tamm. "Sulfur and SeleniumActivation by Frustrated NHC/B(C6F5)3 Lewis Pairs; Conformational Flexibility of Products." Zeitschrift für Naturforschung B 66, no. 4 (April 1, 2011): 371–77. http://dx.doi.org/10.1515/znb-2011-0406.

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Frustrated Lewis pairs consisting of N-heterocyclic carbenes (NHC) and the borane B(C6F5)3 react with elemental sulfur or selenium to give products of the type NHC-E-B(C6F5)3, where E is S or Se. Three such products, two with sulfur and one with selenium, were characterized by X-ray diffraction and shown to exhibit considerable conformational flexibility, as revealed by differing torsion angles in the atom sequence N-C-E-B-Cipso-Cortho. In the sulfur derivatives, the S-B bonds are all long (ca. 2.05 Å), and the C-S bonds (ca. 1.73 Å) are clearly lengthened compared to imidazole-2-thiones. The Se-B distance of 2.2111 Å is the first selenone-borane bond length to be determined by X-ray analysis.

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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

Wang, Chang-Ling, Jie Wang, Ji-Kang Jin, Bin Li, Yee Lin Phang, Feng-Lian Zhang, Tian Ye, et al. "Boryl radical catalysis enables asymmetric radical cycloisomerization reactions." Science 382, no. 6674 (December 2023): 1056–65. http://dx.doi.org/10.1126/science.adg1322.

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The development of functionally distinct catalysts for enantioselective synthesis is a prominent yet challenging goal of synthetic chemistry. In this work, we report a family of chiral N -heterocyclic carbene (NHC)–ligated boryl radicals as catalysts that enable catalytic asymmetric radical cycloisomerization reactions. The radical catalysts can be generated from easily prepared NHC-borane complexes, and the broad availability of the chiral NHC component provides substantial benefits for stereochemical control. Mechanistic studies support a catalytic cycle comprising a sequence of boryl radical addition, hydrogen atom transfer, cyclization, and elimination of the boryl radical catalyst, wherein the chiral NHC subunit determines the enantioselectivity of the radical cyclization. This catalysis allows asymmetric construction of valuable chiral heterocyclic products from simple starting materials.

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7

Dübek, Gizem, Daniel Franz, Carsten Eisenhut, Philipp J. Altmann, and Shigeyoshi Inoue. "Reactivity of an NHC-stabilized pyramidal hydrosilylene with electrophilic boron sources." Dalton Transactions 48, no. 17 (2019): 5756–65. http://dx.doi.org/10.1039/c9dt00608g.

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An NHC-stabilized three-coordinate hydrosilylene dehydrogenates ammonia borane and forms more stable complexes with BH₃, BPh₃, BBr₃ and BPhBr₂ but less stable ones with BF₃, and BCl₃ for which ligand scrambling occurs.

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8

Böser, Richard, Lars Denker, and René Frank. "Benzyl Borane NHC Adducts: Beyond B−C Bond Scission." Chemistry – A European Journal 25, no. 45 (July 17, 2019): 10575–79. http://dx.doi.org/10.1002/chem.201902698.

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9

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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10

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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11

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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12

Ai, Dongxia, Yi Guo, Wei Liu, and Yong Wang. "DFT studies on catalytic dehydrogenation of ammonia borane by Ni(NHC)2." Journal of Physical Organic Chemistry 27, no. 7 (May 15, 2014): 597–603. http://dx.doi.org/10.1002/poc.3306.

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13

Theuergarten, Eileen, Thomas Bannenberg, Marc D. Walter, Dirk Holschumacher, Matthias Freytag, Constantin G. Daniliuc, Peter G. Jones, and Matthias Tamm. "Computational and experimental investigations of CO2and N2O fixation by sterically demanding N-heterocyclic carbenes (NHC) and NHC/borane FLP systems." Dalton Trans. 43, no. 4 (2014): 1651–62. http://dx.doi.org/10.1039/c3dt52742e.

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14

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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15

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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16

Deis, Thomas, Fabrizio Medici, Antoine Poussard-Schulz, Gilles Lemière, and Louis Fensterbank. "Synthesis and reactivity of an anionic NHC-borane featuring a weakly coordinating silicate anion." Journal of Organometallic Chemistry 956 (December 2021): 122120. http://dx.doi.org/10.1016/j.jorganchem.2021.122120.

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17

Brahmi, Malika Makhlouf, Julien Monot, Marine Desage-El Murr, Dennis P. Curran, Louis Fensterbank, Emmanuel Lacôte, and Max Malacria. "Preparation of NHC Borane Complexes by Lewis Base Exchange with Amine− and Phosphine−Boranes." Journal of Organic Chemistry 75, no. 20 (October 15, 2010): 6983–85. http://dx.doi.org/10.1021/jo101301d.

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18

Zhang, Yi, Ping Wang, Yun Gao, Ye Zhang, Zheng-Hang Qi, Wei Liu, and Yong Wang. "Mechanistic insights into tandem amine-borane dehydrogenation and alkene hydrogenation catalyzed by [Pd(NHC)(PCy3)]." International Journal of Hydrogen Energy 43, no. 4 (January 2018): 2043–49. http://dx.doi.org/10.1016/j.ijhydene.2017.12.051.

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19

Tehfe, Mohamad-Ali, Julien Monot, Max Malacria, Louis Fensterbank, Jean-Pierre Fouassier, Dennis P. Curran, Emmanuel Lacôte, and Jacques Lalevée. "A Water-Compatible NHC-Borane: Photopolymerizations in Water and Rate Constants for Elementary Radical Reactions." ACS Macro Letters 1, no. 1 (November 18, 2011): 92–95. http://dx.doi.org/10.1021/mz200087g.

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20

Chen, Chaohuang, Jun Li, Constantin G. Daniliuc, Christian Mück‐Lichtenfeld, Gerald Kehr, and Gerhard Erker. "The [(NHC)B(H)C 6 F 5 ] + Cations and Their [B](H)−CO Borane Carbonyls." Angewandte Chemie 132, no. 48 (September 24, 2020): 21644–48. http://dx.doi.org/10.1002/ange.202009353.

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21

Chen, Chaohuang, Jun Li, Constantin G. Daniliuc, Christian Mück‐Lichtenfeld, Gerald Kehr, and Gerhard Erker. "The [(NHC)B(H)C 6 F 5 ] + Cations and Their [B](H)−CO Borane Carbonyls." Angewandte Chemie International Edition 59, no. 48 (September 24, 2020): 21460–64. http://dx.doi.org/10.1002/anie.202009353.

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22

Xia, Peng‐Ju, Dan Song, Zhi‐Peng Ye, Yuan‐Zhuo Hu, Jun‐An Xiao, Hao‐Yue Xiang, Xiao‐Qing Chen, and Hua Yang. "Photoinduced Single‐Electron Transfer as an Enabling Principle in the Radical Borylation of Alkenes with NHC–Borane." Angewandte Chemie International Edition 59, no. 17 (January 21, 2020): 6706–10. http://dx.doi.org/10.1002/anie.201913398.

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23

Xia, Peng‐Ju, Dan Song, Zhi‐Peng Ye, Yuan‐Zhuo Hu, Jun‐An Xiao, Hao‐Yue Xiang, Xiao‐Qing Chen, and Hua Yang. "Photoinduced Single‐Electron Transfer as an Enabling Principle in the Radical Borylation of Alkenes with NHC–Borane." Angewandte Chemie 132, no. 17 (April 20, 2020): 6772–76. http://dx.doi.org/10.1002/ange.201913398.

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24

Fortman, George C., Alexandra M. Z. Slawin, and Steven P. Nolan. "Highly Active Iridium(III)–NHC System for the Catalytic B–N Bond Activation and Subsequent Solvolysis of Ammonia–Borane." Organometallics 30, no. 20 (October 24, 2011): 5487–92. http://dx.doi.org/10.1021/om2007437.

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25

Yang, Xinzheng, and Michael B. Hall. "Density functional theory study of the mechanism for Ni(NHC)2 catalyzed dehydrogenation of ammonia–borane for chemical hydrogen storage." Journal of Organometallic Chemistry 694, no. 17 (August 2009): 2831–38. http://dx.doi.org/10.1016/j.jorganchem.2009.04.018.

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26

Zhai, Xiaofang, Maofu Pang, Lei Feng, Jiong Jia, Chen-Ho Tung, and Wenguang Wang. "Dehydrogenation of Iron Amido-Borane and Resaturation of the Imino-Borane Complex." Chemical Science, 2021. http://dx.doi.org/10.1039/d0sc06787c.

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We report on the first isolation and structural characterization of an iron imino-borane complex Cp*Fe(η²-H₂B=NC₆H₄PPh₂) by dehydrogenation of iron amido-borane precursor Cp*Fe(η¹-H₃B-NHC₆H₄PPh₂). Significantly, regeneration of the amido-borane complex has been...

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27

Miao, Yu-Qi, Qiao-Jing Pan, Zhenxing Liu, and Xuenian Chen. "Visible-light-Induced 1,2-Diphenyldisulfane-Catalyzed Regioselective Hydroboration of Electron-Deficient Alkenes." New Journal of Chemistry, 2022. http://dx.doi.org/10.1039/d2nj03930c.

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A green and practical photoinduced method for regioselective hydroboration of electron-deficient alkenes with NHC-borane has been developed in which 1,2-diphenyldisulfane was employed as photocatalyst and hydrogen atom transfer (HAT) reagent...

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28

Kundu, Gargi, Ruchi Dixit, Srinu Tothadi, Kumar Vanka, and Sakya Singha Sen. "Versatile chemistry of six-membered NHC with boranes: bromination at sp3 borane, activation of B–H bond of HBpin, and ring expansion of NHC." Dalton Transactions, 2022. http://dx.doi.org/10.1039/d2dt01707e.

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The NHC•borane chemistry has been majorly restricted to imidazol-2-ylidene classes of carbenes. In our previous communication, we have reported the synthesis of 6-SIDipp•BH3 [6-SIDipp = 1,3-di(2,6-diisopropylphenyl) tetrahydropyrimidine-2-ylidene] and its electrophilic...

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29

Zhang, Feng-Lian, Yi-Feng Wang, Bi-Yang Zhuang, and Ji-Kang Jin. "Radical-Hydroboration-Involved One-Pot Synthesis of Boron-Handled Glycol Derivatives." Synlett, June 16, 2020. http://dx.doi.org/10.1055/s-0040-1707142.

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A one-pot two-step protocol for the direct synthesis of boron-handled glycol derivatives is reported. The procedure starts by an NHC–boryl-radical-promoted regioselective hydroboration of glycol-protected cinnamaldehydes. After that, the reaction mixture is treated with pinacol in the presence of HCl, leading to the direct formation of pinacol boronate handled glycol monoalkyl ethers. In this acid-triggered conversion, a reductive ring-opening of glycol-derived acetal moiety takes place, during which an NHC–borane unit serves as the hydride source.

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30

Bellec, Romane, Romain Godelier, Lionel Joucla, Anne Renault, and Emmanuel Lacote. "Preparation of Mono and Bis‐Hydrazino‐Substituted N‐Heterocyclic Carbene Boranes." European Journal of Organic Chemistry, October 12, 2023. http://dx.doi.org/10.1002/ejoc.202300806.

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We report the formation of NHC complexes of mono‐ and bis‐hydrazino boranes with N–N–B and N–N–B–N–N chains via the reaction of NHC‐boranes with electrophilic azo reagents. The influence of steric hindrance on the carbene and on the azo reagent has been shown to be crucial for the reactivity. The hydroboration of dissymmetric azo reagents is regioselective only when the latter is sufficiently electronically twisted. Bis‐hydrazino borane complexes with two different hydrazine arms could be obtained via sequential addition.

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31

Xie, Fukai, Zhan Mao, Dennis P. Curran, Hongliang Liang, and Wen Dai. "Facile Borylation of Alkenes, Alkynes, Imines, Arenes and Heteroarenes with N‐Heterocyclic Carbene‐Boranes and a Heterogeneous Semiconductor Photocatalyst." Angewandte Chemie International Edition, August 9, 2023. http://dx.doi.org/10.1002/anie.202306846.

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Although the development of radical chain and photocatalytic borylation reactions using N‐heterocyclic carbene (NHC)‐borane as boron source is remarkable, the persistent problems, including the use of hazardous and high‐energy radical initiators or the recyclability and photostability issues of soluble homogeneous photocatalysts, still leave great room for further development in a sustainable manner. Herein, we report a conceptually different approach toward highly functionalized organoborane synthesis by using recoverable ultrathin cadmium sulfide (CdS) nanosheets as a heterogeneous photocatalyst, and a general and mild borylation platform that enables regioselective borylation of a wide variety of alkenes (arylethenes, trifluoromethylalkenes, α,β‐unsaturated carbonyl compounds and nitriles), alkynes, imines and electron‐poor aromatic rings with NHC‐borane as boryl radical precursor. Mechanistic studies and density functional theory (DFT) calculations reveal that both photogenerated electrons and holes on the CdS fully perform their own roles, thereby resulting in enhancement of photocatalytic activity and stability of CdS.

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32

Xie, Fukai, Zhan Mao, Dennis P. Curran, Hongliang Liang, and Wen Dai. "Facile Borylation of Alkenes, Alkynes, Imines, Arenes and Heteroarenes with N‐Heterocyclic Carbene‐Boranes and a Heterogeneous Semiconductor Photocatalyst." Angewandte Chemie, August 9, 2023. http://dx.doi.org/10.1002/ange.202306846.

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Although the development of radical chain and photocatalytic borylation reactions using N‐heterocyclic carbene (NHC)‐borane as boron source is remarkable, the persistent problems, including the use of hazardous and high‐energy radical initiators or the recyclability and photostability issues of soluble homogeneous photocatalysts, still leave great room for further development in a sustainable manner. Herein, we report a conceptually different approach toward highly functionalized organoborane synthesis by using recoverable ultrathin cadmium sulfide (CdS) nanosheets as a heterogeneous photocatalyst, and a general and mild borylation platform that enables regioselective borylation of a wide variety of alkenes (arylethenes, trifluoromethylalkenes, α,β‐unsaturated carbonyl compounds and nitriles), alkynes, imines and electron‐poor aromatic rings with NHC‐borane as boryl radical precursor. Mechanistic studies and density functional theory (DFT) calculations reveal that both photogenerated electrons and holes on the CdS fully perform their own roles, thereby resulting in enhancement of photocatalytic activity and stability of CdS.

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33

Morales, Agustin, Caroline Gonçalves, Alix Sournia-Saquet, Laure Vendier, Agusti Lledos, Olivier Basle, and Sébastien Bontemps. "Single electron reduction of NHC-CO2-borane compounds." Chemical Science, 2024. http://dx.doi.org/10.1039/d3sc06325a.

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Carbon dioxide radical anion [CO2•] is a highly reactive species of fundamental and synthetic interest. However, the direct one-electron reduction of CO2 to generate [CO2•] occurs at very negative reduction...

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34

Fan, Jun, An-Ping Koh, Chi-Shiun Wu, Ming-Der Su, and Cheuk-Wai So. "Carbon dioxide capture and functionalization by bis(N-heterocyclic carbene)-borylene complexes." Nature Communications 15, no. 1 (April 9, 2024). http://dx.doi.org/10.1038/s41467-024-47381-7.

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AbstractDerivatives of free monocoordinated borylenes have attracted considerable interest due to their ability to exhibit transition-metal-like reactivity, in particular small molecules capture. However, such complexes are rare as the formation is either endergonic, or the resulting adduct is a transient intermediate that is prone to reaction. Here, we present the synthesis of two bis(N-heterocyclic carbene)-borylene complexes capable of capturing and functionalizing carbon dioxide. The capture and subsequent functionalization of CO2 by the bis(NHC)-disilylamidoborylene 1 is demonstrated by the formation of the bis(NHC)-isocyanatoborylene-carbon dioxide complex 3. Reversible capture of CO2 is observed using the bis(NHC)-mesitylborylene 2, and the persistent bis(NHC)-mesitylborylene-carbon dioxide adduct 4 can be stabilized by hydrogen bonding with boric acid. The reactions of 4 with ammonia-borane and aniline demonstrate that the captured CO2 can be further functionalized.

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35

Zeng, Yao-Fu, Xin Wu, Yue Wang, Ming-Xi Zhou, Zhang Chen, Xue Peng, and Zhen Wang. "Switchable access to mono‐ and di‐alkylated boranes via visible‐light‐induced hydroboration of alkenes with NHC‐borane." Advanced Synthesis & Catalysis, September 22, 2023. http://dx.doi.org/10.1002/adsc.202300863.

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A photo‐induced metal‐free radical hydroboration of various styrenes with NHC‐borane has been developed, which can provide mono‐ and di‐alkylated boranes in a selective manner. Besides, this strategy can also be applied to prepare di‐functionalized boranes with two different alkyl groups. Mild reaction conditions and good functional groups compatibility were observed. Preliminary mechanism for this reaction was proposed.

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36

Bo, Ming-Cheng, Yee Lin Phang, Qiang Zhao, Feng-Lian Zhang, and Yi-Feng Wang. "Lewis Base‐Boryl Radicals Promoted Selective Mono‐ and Di‐hydrodechlorination of Trichloroacetamides and Acetates." European Journal of Organic Chemistry, December 20, 2023. http://dx.doi.org/10.1002/ejoc.202301189.

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Mono and dichloro‐substituted organic molecules are shown to possess significant roles in various fields, especially in medicinal chemistry. One approach to synthesizing these compounds involves the selective dechlorination of easily prepared trichloromethyl compounds. Nevertheless, developing a practical approach that allows selective mono‐ and dihydrodechlorination is a challenging task. Herein, we introduced a method for selective mono‐ and dihydrodechlorination of trichloroacetamides and acetates which was promoted by two different Lewis base‐boryl radicals. Accordingly, 4‐dimethylaminopyridine (DMAP)‐borane enabled mono‐substitution of chlorine atom by hydrogen while dihydro‐substitution of chlorine atoms was promoted by N‐heterocyclic carbene (NHC)‐boryl radical. Using deuterated Lewis base‐borane as deuterium atom source, mono‐ and dideuterodechlorination were also successfully took place. This protocol features broad substrate scope and operates under mild reaction conditions.

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37

Sharma, Mahendra K., Hanns M. Weinert, Christoph Wölper, and Stephan Schulz. "Gallaphosphene L(Cl)GaPGaL: A novel phosphinidene transfer reagent." Chemistry – A European Journal, January 18, 2024. http://dx.doi.org/10.1002/chem.202400110.

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Gallaphosphene L(Cl)GaPGaL 1 (L = HC[C(Me)N(Ar)]2; Ar = 2,6‐i‐Pr2C6H3) reacts with N‐heterocyclic carbenes RNHC (RNHC = [CMeN(R)]2C; R = Me, iPr) to RNHC‐coordinated phosphinidenes L(Cl)GaP←RNHC (R = Me 2a, iPr 2b) and with isonitriles RNC (R = iPr, Cy) to 1,3‐phosphaazaallenes L(Cl)GaP=C=N‐R (R = iPr 3a, Cy 3b), respectively. Quantum chemical calculations reveal that 2a/2b possesses two localized lone pair of electrons, whereas 3a/3b only show one localized lone pair as was reported for gallaphosphene 1. 2b reacts with 2.5 equivalents of a borane (THF•BH3) to the NHC‐stabilized phosphinidene‐borane complex [iPrNHC→P(BH2)]2(BH3)34 with concomitant formation of LGa(H)Cl 5. 2–5 are characterized by heteronuclear (1H, 13C{1H}, 31P{1H}) NMR and IR spectroscopy, elemental analysis, and single crystal X‐ray diffraction (sc‐XRD).

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38

Zhang, Qiao, Wengang Xu, Qiong Liu, Congjian Xia, Qi Shao, Lishuang Ma, and Mingbo Wu. "Diastereoselective dearomatization of indoles via photocatalytic hydroboration on hydramine-functionalized carbon nitride." Nature Communications 15, no. 1 (May 22, 2024). http://dx.doi.org/10.1038/s41467-024-48769-1.

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AbstractA protocol for trans-hydroboration of indole derivatives using heterogeneous photocatalysis with NHC-borane has been developed, addressing a persistent challenge in organic synthesis. The protocol, leveraging high crystalline vacancy-engineered polymeric carbon nitride as a catalyst, enables diastereoselective synthesis, expanding substrate scope and complementing existing methods. The approach emphasizes eco-friendliness, cost-effectiveness, and scalability, making it suitable for industrial applications, particularly in renewable energy contexts. The catalyst’s superior performance, attributed to its rich carbon-vacancies and well-ordered structure, surpasses more expensive homogeneous alternatives, enhancing viability for large-scale use. This innovation holds promise for synthesizing bioactive compounds and materials relevant to medicinal chemistry and beyond.

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39

Ackermann, Matthias, Robert Szlosek, Christoph Riesinger, Michael Seidl, Alexey Timoshkin, Eric Rivard, and Manfred Scheer. "NHC‐Stabilized Mixed Group 13/14/15 Element Hydrides." Chemistry – A European Journal, November 27, 2023. http://dx.doi.org/10.1002/chem.202303680.

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The syntheses of novel N‐heterocyclic carbene (NHC) adducts of group 13, 14 and 15 element hydrides are reported. Salt metathesis reactions between NaPH2 and IDipp·GeH2BH2OTf (1) (IDipp = 1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene) led to mixtures of the two isomers IDipp·GeH2BH2PH2 (2a) and IDipp·BH2GeH2PH2 (2b); by altering the reaction conditions an almost exclusive formation of 2b was achieved. Attempts to purify mixtures of 2a and 2b by re‐crystallization from THF afforded a salt [IDipp·GeH2BH2·IDipp][PHGeH2BH2PH2BH2GeH2] (4) that contains the novel anionic cyclohexyl‐like inorganic heterocycle [PHGeH2BH2PH2BH2GeH2]‐. In addition, the borane adducts IDipp·GeH2BH2PH2BH3 (3a) and IDipp·BH2GeH2PH2BH3 (3b) as even longer chain compounds were obtained from reactions of 2a/2b with H3B·SMe2 and were studied by NMR spectroscopy. Accompanying DFT computations give insight into the mechanism and energetics associated with 2a/2b isomerization as well as their decomposition pathways.

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40

Miao, Yu-Qi, Qiao-Jing Pan, Jiaxin Kang, Xusheng Dai, Zhenxing Liu, and Xuenian Chen. "A Green and Facile Photochemical Thiolate-Catalyzed Strategy for Borylation of Aryl Fluorides with NHC-Borane." Organic Chemistry Frontiers, 2024. http://dx.doi.org/10.1039/d4qo00058g.

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Direct C-F bond borylation of polyfluoroarenes is a straightforward way to obtain poly-fluorinated organoboron compounds, valuable building blocks for bioactive and material molecules. However, the high BDE of C-F bonds...

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41

Camy, Aurèle, Laure Vendier, Christian Bijani, Israel Fernández, and Sébastien Bontemps. "Synthesis and Coordination of a Bisphosphine-[NHC-borane] Compound: A Ligand Framework for Bimetallic Structure Featuring a Boron-Bridging Moiety." Inorganic Chemistry, May 26, 2023. http://dx.doi.org/10.1021/acs.inorgchem.3c00785.

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