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Journal articles on the topic 'Hydrogen Borrowing Reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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1

Shermer, Duncan J., Paul A. Slatford, Dean D. Edney, and Jonathan M. J. Williams. "Borrowing hydrogen in an indirect asymmetric Wittig reaction." Tetrahedron: Asymmetry 18, no. 24 (December 2007): 2845–48. http://dx.doi.org/10.1016/j.tetasy.2007.11.019.

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2

WANG, Chao. "Borrowing Hydrogen Reaction with Alcohols and Amines by Homogeneous Catalysis." University Chemistry 31, no. 10 (2016): 1–9. http://dx.doi.org/10.3866/pku.dxhx201606001.

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3

Wang, Danfeng, Roy T. McBurney, Indrek Pernik, and Barbara A. Messerle. "Controlling the selectivity and efficiency of the hydrogen borrowing reaction by switching between rhodium and iridium catalysts." Dalton Transactions 48, no. 37 (2019): 13989–99. http://dx.doi.org/10.1039/c9dt02819f.

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4

Huang, Ronghui, Yongchun Yang, Duo-Sheng Wang, Liang Zhang, and Dawei Wang. "Where does Au coordinate to N-(2-pyridiyl)benzotriazole: gold-catalyzed chemoselective dehydrogenation and borrowing hydrogen reactions." Organic Chemistry Frontiers 5, no. 2 (2018): 203–9. http://dx.doi.org/10.1039/c7qo00756f.

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5

Xu, Zhaojun, Xiaoli Yu, Xinxin Sang, and Dawei Wang. "BINAP-copper supported by hydrotalcite as an efficient catalyst for the borrowing hydrogen reaction and dehydrogenation cyclization under water or solvent-free conditions." Green Chemistry 20, no. 11 (2018): 2571–77. http://dx.doi.org/10.1039/c8gc00557e.

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A BINAP-Cu system supported by hydrotalcite has been developed and proved to be a highly efficient catalyst for the atom-efficient and green borrowing hydrogen reaction and dehydrogenative cyclization.

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6

Çiçek, Metin, Nevin Gürbüz, Namık Özdemir, İsmail Özdemir, and Esin İspir. "Half-sandwich Ru(ii) arene complexes bearing benzimidazole ligands for the N-alkylation reaction of aniline with alcohols in a solvent-free medium." New Journal of Chemistry 45, no. 25 (2021): 11075–85. http://dx.doi.org/10.1039/d1nj01539g.

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7

Newland, R. J., M. F. Wyatt, R. L. Wingad, and S. M. Mansell. "A ruthenium(ii) bis(phosphinophosphinine) complex as a precatalyst for transfer-hydrogenation and hydrogen-borrowing reactions." Dalton Transactions 46, no. 19 (2017): 6172–76. http://dx.doi.org/10.1039/c7dt01022b.

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A Ru(ii) complex with 2-phosphinophosphinine ligands activated with KO^tBu catalyses the room temperature transfer hydrogenation of acetophenone and the hydrogen-borrowing reaction of MeOH/EtOH to the advanced biofuel isobutanol.

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8

Feng, Si Min, and Qing Liu. "Research Progress of N-Alkylation of Alcohol and Amine by "Hydrogen Reaction"." Key Engineering Materials 871 (January 2021): 312–17. http://dx.doi.org/10.4028/www.scientific.net/kem.871.312.

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Amine compounds are widely found in natural products, pharmaceuticals and fine chemical products. Therefore, it is of great significance to develop methods for synthesizing amine compounds. Therefore, in recent years, a new method of synthesizing amines has been developed, namely "hydrogen borrowing reaction". This article reviews the alkylation of primary alcohols and amines, the cyclization of amino alcohols to form N-heterocyclic compounds, the reaction of diols and amines to form N-heterocyclic compounds, the reaction of alcohols and sulfonamides, and the reaction of alcohols and amines containing N heteroatoms , Alcohol and ammonia gas and ammonia to produce amine by hydrogen reaction research progress.

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9

Llabres-Campaner, Pedro J., Rafael Ballesteros-Garrido, Rafael Ballesteros, and Belén Abarca. "β-Amino alcohols from anilines and ethylene glycol through heterogeneous Borrowing Hydrogen reaction." Tetrahedron 73, no. 37 (September 2017): 5552–61. http://dx.doi.org/10.1016/j.tet.2017.08.006.

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10

Nakayama, Taku, Hidemasa Hikawa, Shoko Kikkawa, and Isao Azumaya. "Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy." RSC Advances 11, no. 37 (2021): 23144–50. http://dx.doi.org/10.1039/d1ra04118e.

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11

Liu, Xianglei, and Zhenhua Gu. "Pd-catalyzed Heck cyclization and in situ hydrocarboxylation or hydromethenylation via a hydrogen borrowing strategy." Organic Chemistry Frontiers 2, no. 7 (2015): 778–82. http://dx.doi.org/10.1039/c5qo00091b.

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12

Ye, Si-Pei, Yi-Bi Xie, Ke-Yan Zhao, Yang Liu, Jian Yang, De-Jiang Li, and Long Wang. "Synthesis, structures, photophysical and catalytic properties of benzothienyl iridium(III) complexes." Journal of Chemical Research 41, no. 5 (May 2017): 287–90. http://dx.doi.org/10.3184/174751917x14931195075562.

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Bisbenzothienyl iridium(III) complexes, [Ir(bt)2(PR3)]X (bt: 2-phenylbenzo[ d]thiazole, R = n-Bu or Ph, X = OTf, BF4 or SbF6) are reported, two of which, (R = n-Bu or Ph, X = OTf), have been characterised by X-ray crystallography. The complexes are thermally stable and their photophysical properties are presented, together with their catalytic activity in the “borrowing hydrogen reaction” of alcohols with amines.

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13

Song, Tao, Yanan Duan, Xiufang Chen, and Yong Yang. "Switchable Access to Amines and Imines from Reductive Coupling of Nitroarenes with Alcohols Catalyzed by Biomass-Derived Cobalt Nanoparticles." Catalysts 9, no. 2 (January 29, 2019): 116. http://dx.doi.org/10.3390/catal9020116.

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Cobalt nanoparticles modified with N-doped hierarchical porous carbon derived from biomass are found to be a highly efficient, reusable heterogeneous catalyst for the coupling of nitroarenes with alcohols, selectively affording imines and amines via the borrowing hydrogen strategy for the first time. The product selectivity between imine and amine may be precisely tuned by simple alteration of the reaction conditions without changing the catalyst in one reaction system. In this study, a broad set of complex imines and amines was successfully synthesized in good to high yields with various functional groups tolerated for both nitroarenes and alcohols, highlighting the potentially practical utility of the protocol. This heterogeneous catalyst can be easily removed from the reaction medium by external magnet and can be reused at least four times without significant loss in activity and selectivity.

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14

Yao, Wei, Zheng‐Chao Duan, Yilin Zhang, Xinxin Sang, Xiao‐Feng Xia, and Dawei Wang. "Iridium Supported on Phosphorus‐Doped Porous Organic Polymers: Active and Recyclable Catalyst for Acceptorless Dehydrogenation and Borrowing Hydrogen Reaction." Advanced Synthesis & Catalysis 361, no. 24 (November 7, 2019): 5695–703. http://dx.doi.org/10.1002/adsc.201900929.

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15

Donthireddy, S. N. R., Vipin K. Pandey, and Arnab Rit. "[(PPh3)2NiCl2]-Catalyzed C–N Bond Formation Reaction via Borrowing Hydrogen Strategy: Access to Diverse Secondary Amines and Quinolines." Journal of Organic Chemistry 86, no. 9 (April 27, 2021): 6994–7001. http://dx.doi.org/10.1021/acs.joc.1c00510.

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16

Hu, Xinyu, Haiyan Zhu, Xinxin Sang, and Dawei Wang. "Design and Synthesis of Zirconium-Containing Coordination Polymer Based on Unsymmetric Indolyl Dicarboxylic Acid and Catalytic Application on Borrowing Hydrogen Reaction." Advanced Synthesis & Catalysis 360, no. 22 (September 26, 2018): 4293–300. http://dx.doi.org/10.1002/adsc.201800875.

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17

Moulay, Saad. "N-Methylation of Nitrogen-Containing Organic Substrates: A Comprehensive Overview." Current Organic Chemistry 23, no. 16 (November 8, 2019): 1695–737. http://dx.doi.org/10.2174/1385272823666190823114547.

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The present account surveys the results of the plethora of works on Nmethylation of nitrogen-containing substrates, mainly amines. The countless reports in the literature on this issue reveal the emergence of a set of methylating agents, which include: methanol, dimethyl carbonate, formaldehyde/formic acid, carbon dioxide/reductant, methyl iodide, dimethylsulfate, peroxides, dimethylsulfoxide, tetramethylammonium salts, and other unusual ones. Types of the methylating agents including, catalyst, solvent, base, ligand, reducing agent and other reaction conditions such as temperature and time would greatly affect the extent of selectivity of N-monomethylation vis-à-vis N,N-dimethylation. The degree of acidity or alkalinity of catalysts such as the solid catalysts (i.e. zeolites) showed a substantial impact on the selectivity and the course of methylation, leading to design adequate catalysts or to bring suitable modifications to the existing ones. Although this account takes into consideration all types of methylating agents, it is worthwhile to mention that the relatively recent works have been focused on the utilization of eco-friendly methylating agents, including carbon dioxide/reductant, methanol, and dimethylcarbonate. N-Methyl-containing drugs were successfully synthesized with some methylating agents under specified conditions. In some instances, unexpected products and events from the planned N-methylation of some nitrogen-containing molecules occurred. N-Formylation occurred as an intermediate or concomitant reaction when amines were subjected to catalyze methylation with methanol, formaldehyde/ formic acid, and carbon dioxide/reductant. The occasionally depicted mechanisms would elucidate the carbon and hydrogen sources of the affixing methyl group on the nitrogen site. Peculiarly, methylation involving methanol as a methylating agent and transition metal catalysis called for borrowing hydrogen process as a new mechanistic approach.

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18

Shen, Di, Darren L. Poole, Camilla C. Shotton, Anne F. Kornahrens, Mark P. Healy, and Timothy J. Donohoe. "Hydrogen-Borrowing and Interrupted-Hydrogen-Borrowing Reactions of Ketones and Methanol Catalyzed by Iridium." Angewandte Chemie 127, no. 5 (December 9, 2014): 1662–65. http://dx.doi.org/10.1002/ange.201410391.

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19

Shen, Di, Darren L. Poole, Camilla C. Shotton, Anne F. Kornahrens, Mark P. Healy, and Timothy J. Donohoe. "Hydrogen-Borrowing and Interrupted-Hydrogen-Borrowing Reactions of Ketones and Methanol Catalyzed by Iridium." Angewandte Chemie International Edition 54, no. 5 (December 9, 2014): 1642–45. http://dx.doi.org/10.1002/anie.201410391.

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20

Shen, Di, Darren L. Poole, Camilla C. Shotton, Anne F. Kornahrens, Mark P. Healy, and Timothy J. Donohoe. "ChemInform Abstract: Hydrogen-Borrowing and Interrupted-Hydrogen-Borrowing Reactions of Ketones and Methanol Catalyzed by Iridium." ChemInform 46, no. 24 (May 27, 2015): no. http://dx.doi.org/10.1002/chin.201524050.

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21

Shimizu, Ken-ichi. "Heterogeneous catalysis for the direct synthesis of chemicals by borrowing hydrogen methodology." Catalysis Science & Technology 5, no. 3 (2015): 1412–27. http://dx.doi.org/10.1039/c4cy01170h.

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This review summarizes the recent examples of hydrogen transfer-type reactions using supported transition metal catalysts with special emphasis on the one-pot synthesis of chemicals by borrowing hydrogen methodology.

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22

Wei, Duo, Chakkrit Netkaew, and Christophe Darcel. "Multi-Step Reactions Involving Iron-Catalysed Reduction and Hydrogen Borrowing Reactions." European Journal of Inorganic Chemistry 2019, no. 20 (April 8, 2019): 2471–87. http://dx.doi.org/10.1002/ejic.201900122.

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23

Wei, Duo, Chakkrit Netkaew, and Christophe Darcel. "Multi-Step Reactions Involving Iron-Catalysed Reduction and Hydrogen Borrowing Reactions." European Journal of Inorganic Chemistry 2019, no. 20 (May 16, 2019): 2469. http://dx.doi.org/10.1002/ejic.201900504.

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24

Ovezova, Mamajan, Zafer Eroğlu, Önder Metin, Bekir Çetinkaya, and Süleyman Gülcemal. "Unveiling the catalytic nature of palladium-N-heterocyclic carbene catalysts in the α-alkylation of ketones with primary alcohols." Dalton Transactions 50, no. 31 (2021): 10896–908. http://dx.doi.org/10.1039/d1dt01704g.

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25

Luo, Huanhuan, Yike Yang, Bobin Yang, Zhaojun Xu, and Dawei Wang. "Silver/manganese dioxide nanorod catalyzed hydrogen-borrowing reactions and tert-butyl ester synthesis." Journal of Chemical Research 45, no. 7-8 (February 25, 2021): 708–15. http://dx.doi.org/10.1177/1747519821989963.

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Silver/manganese dioxide (Ag@MnO2) nanorods are synthesized and characterized by scanning electron microscopy, transmission electron microscopy, energy dispersive X-ray spectroscopy, X-ray powder diffraction, and X-ray photoelectron spectroscopy. It was discovered that Ag@MnO2 nanorods can realize hydrogen-borrowing reactions in high yields and are also effective for the synthesis of tert-butyl esters from aryl cyanides and tert-butyl hydroperoxide in a short period of time. Mechanistic experiments revealed that this catalytic system acts as a Lewis acid in hydrogen-borrowing reactions, while the synthesis of tert-butyl esters occurs through a radical pathway. This is the first report on the excellent catalytic activity of Ag@MnO2 nanorods as a catalyst.

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26

Nixon, Tracy D., Michael K. Whittlesey, and Jonathan M. J. Williams. "Transition metal catalysed reactions of alcohols using borrowing hydrogen methodology." Dalton Trans., no. 5 (2009): 753–62. http://dx.doi.org/10.1039/b813383b.

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27

Di Gregorio, Giovanni, Michele Mari, Silvia Bartolucci, Francesca Bartoccini, and Giovanni Piersanti. "Divergent reactions of oxindoles with amino alcohols via the borrowing hydrogen process: oxindole ring opening vs. C3 alkylation." Organic Chemistry Frontiers 5, no. 10 (2018): 1622–27. http://dx.doi.org/10.1039/c8qo00184g.

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Oxindoles react with N-acetyl amino alcohols to form tryptamine-derived oxindoles, whereas analogous reactions with N-alkyl amino alcohols lead to lactam formation via a relatively mild borrowing hydrogen process.

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28

Pothikumar, Rajagopal, Venugopal T. Bhat, and Kayambu Namitharan. "Pyridine mediated transition-metal-free direct alkylation of anilines using alcohols via borrowing hydrogen conditions." Chemical Communications 56, no. 88 (2020): 13607–10. http://dx.doi.org/10.1039/d0cc05912a.

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Herein, we report aza-aromatics based organic mediators as a readily accessible alternative to the traditional approach of using transition metal catalyst systems for the activation of alcohols in borrowing hydrogen reactions.

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29

Irrgang, Torsten, and Rhett Kempe. "3d-Metal Catalyzed N- and C-Alkylation Reactions via Borrowing Hydrogen or Hydrogen Autotransfer." Chemical Reviews 119, no. 4 (November 20, 2018): 2524–49. http://dx.doi.org/10.1021/acs.chemrev.8b00306.

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30

Llabres-Campaner, Pedro J., Patricia Woodbridge-Ortega, Rafael Ballesteros-Garrido, Rafael Ballesteros, and Belén Abarca. "Heterogeneous borrowing hydrogen reactions with Pd/C and ZnO: Diol scope." Tetrahedron Letters 58, no. 52 (December 2017): 4880–82. http://dx.doi.org/10.1016/j.tetlet.2017.11.039.

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31

Kwok, Timothy, Oskar Hoff, Roly J. Armstrong, and Timothy J. Donohoe. "Control of Absolute Stereochemistry in Transition‐Metal‐Catalysed Hydrogen‐Borrowing Reactions." Chemistry – A European Journal 26, no. 57 (September 11, 2020): 12912–26. http://dx.doi.org/10.1002/chem.202001253.

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32

Obora, Yasushi. "Recent Advances in α-Alkylation Reactions using Alcohols with Hydrogen Borrowing Methodologies." ACS Catalysis 4, no. 11 (October 9, 2014): 3972–81. http://dx.doi.org/10.1021/cs501269d.

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33

Bains, Amreen K., Abhishek Kundu, Sudha Yadav, and Debashis Adhikari. "Borrowing Hydrogen-Mediated N-Alkylation Reactions by a Well-Defined Homogeneous Nickel Catalyst." ACS Catalysis 9, no. 10 (August 19, 2019): 9051–59. http://dx.doi.org/10.1021/acscatal.9b02977.

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34

Chelucci, Giorgio. "Ruthenium and osmium complexes in CC bond-forming reactions by borrowing hydrogen catalysis." Coordination Chemistry Reviews 331 (January 2017): 1–36. http://dx.doi.org/10.1016/j.ccr.2016.10.002.

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35

Black, Phillip J., Gerta Cami-Kobeci, Michael G. Edwards, Paul A. Slatford, Michael K. Whittlesey, and Jonathan M. J. Williams. "Borrowing hydrogen: iridium-catalysed reactions for the formation of C–C bonds from alcohols." Org. Biomol. Chem. 4, no. 1 (2006): 116–25. http://dx.doi.org/10.1039/b511053j.

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36

Mansell, S. M. "Catalytic applications of small bite-angle diphosphorus ligands with single-atom linkers." Dalton Transactions 46, no. 44 (2017): 15157–74. http://dx.doi.org/10.1039/c7dt03395h.

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Diphosphorus ligands connected by a single atom (R₂PEPR₂; E = CR₂, CCR₂and NR) give chelating ligands with very small bite-angles as well as enable access to other properties such as bridging modes and hemilability. ThisPerspectivereviews the properties of diphosphorus ligands featuring a single-atom linker and their applications in catalysis, including transformations of alkenes and transfer hydrogenation and hydrogen-borrowing reactions.

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37

Wei, Duo, Chakkrit Netkaew, and Christophe Darcel. "Front Cover: Multi-Step Reactions Involving Iron-Catalysed Reduction and Hydrogen Borrowing Reactions (Eur. J. Inorg. Chem. 20/2019)." European Journal of Inorganic Chemistry 2019, no. 20 (May 16, 2019): 2468. http://dx.doi.org/10.1002/ejic.201900503.

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38

Genç, Sertaç, Burcu Arslan, Süleyman Gülcemal, Salih Günnaz, Bekir Çetinkaya, and Derya Gülcemal. "Iridium(I)-Catalyzed C–C and C–N Bond Formation Reactions via the Borrowing Hydrogen Strategy." Journal of Organic Chemistry 84, no. 10 (April 15, 2019): 6286–97. http://dx.doi.org/10.1021/acs.joc.9b00632.

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39

Zhu, Guanxin, Zheng-Chao Duan, Haiyan Zhu, Minghui Qi, and Dawei Wang. "Iridium and copper supported on silicon dioxide as chemoselective catalysts for dehydrogenation and borrowing hydrogen reactions." Molecular Catalysis 505 (April 2021): 111516. http://dx.doi.org/10.1016/j.mcat.2021.111516.

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40

Yang, Yongchun, Anni Qin, Keyan Zhao, Dawei Wang, and Xiaodong Shi. "Design and Synthesis of Alanine Triazole Ligands and Application in Promotion of Hydration, Allene Synthesis and Borrowing Hydrogen Reactions." Advanced Synthesis & Catalysis 358, no. 9 (April 24, 2016): 1433–39. http://dx.doi.org/10.1002/adsc.201600141.

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41

Yoshida, Kenta, Kenichi Kon, and Ken-ichi Shimizu. "Atomic-Resolution HAADF-STEM Study of Ag/Al2O3 Catalysts for Borrowing-Hydrogen and Acceptorless Dehydrogenative Coupling Reactions of Alcohols." Topics in Catalysis 59, no. 19-20 (August 25, 2016): 1740–47. http://dx.doi.org/10.1007/s11244-016-0695-7.

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42

Kodama, Takuya, Yuki Kawashima, Zhirong Deng, and Mamoru Tobisu. "Synthesis of 4,5-Benzotropone π Complexes of Iron, Rhodium, and Iridium and Their Potential Use in Catalytic Borrowing-Hydrogen Reactions." Inorganic Chemistry 60, no. 7 (March 26, 2021): 4332–36. http://dx.doi.org/10.1021/acs.inorgchem.0c03587.

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43

Sorribes, Iván, and Avelino Corma. "Nanolayered cobalt–molybdenum sulphides (Co–Mo–S) catalyse borrowing hydrogen C–S bond formation reactions of thiols or H2S with alcohols." Chemical Science 10, no. 10 (2019): 3130–42. http://dx.doi.org/10.1039/c8sc05782f.

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44

Qiu, Ye, Yilin Zhang, Lu Jin, Le Pan, Guangming Du, Dongdong Ye, and Dawei Wang. "Immobilization of manganese dioxide nanoparticles on modified poly 2,4-dichlorostyrene microspheres: a highly efficient and recyclable catalyst for borrowing hydrogen reactions." Organic Chemistry Frontiers 6, no. 19 (2019): 3420–27. http://dx.doi.org/10.1039/c9qo00892f.

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45

Xu, Zhaojun, Duo-Sheng Wang, Xiaoli Yu, Yongchun Yang, and Dawei Wang. "Tunable Triazole-Phosphine-Copper Catalysts for the Synthesis of 2-Aryl-1H -benzo[d]imidazoles from Benzyl Alcohols and Diamines by Acceptorless Dehydrogenation and Borrowing Hydrogen Reactions." Advanced Synthesis & Catalysis 359, no. 19 (June 19, 2017): 3332–40. http://dx.doi.org/10.1002/adsc.201700179.

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46

wang, kun, miao xiao, and Chao Wang. "Synthesis of Chiral Amines via Asymmetric Hydrogen Borrowing." Synlett, December 11, 2020. http://dx.doi.org/10.1055/a-1335-7070.

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Chiral amines have been widely used in pharmaceutic, agrochemical and fine-chemical industries. With water as the only byproduct and requiring no extra reducing reagent, the reaction of alcohols with amines via a “hydrogen borrowing” pathway is a green route to prepare chiral amines. This paper gives a brief summary of progresses on asymmetric amination of alcohols to produce chiral amines via the “hydrogen borrowing” strategy.

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47

Kwok, Timothy, Oskar Hoff, Roly J. Armstrong, and Timothy J. Donohoe. "Frontispiece: Control of Absolute Stereochemistry in Transition‐Metal‐Catalysed Hydrogen‐Borrowing Reactions." Chemistry – A European Journal 26, no. 57 (October 9, 2020). http://dx.doi.org/10.1002/chem.202085762.

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48

Nixon, Tracy D., Michael K. Whittlesey, and Jonathan M. J. Williams. "ChemInform Abstract: Transition Metal Catalysed Reactions of Alcohols Using Borrowing Hydrogen Methodology." ChemInform 40, no. 23 (June 9, 2009). http://dx.doi.org/10.1002/chin.200923241.

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49

"Dehydrogenation and Hydrogen-Borrowing Reactions with a P-Doped Polymer-Supported Iridium Catalyst." Synfacts 16, no. 03 (February 18, 2020): 0320. http://dx.doi.org/10.1055/s-0039-1691724.

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50

Obora, Yasushi. "ChemInform Abstract: Recent Advances in α-Alkylation Reactions Using Alcohols with Hydrogen Borrowing Methodologies." ChemInform 46, no. 1 (January 2015). http://dx.doi.org/10.1002/chin.201501247.

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