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Journal articles on the topic 'Hydrosilylation of imines'

Author: Grafiati

Published: 6 September 2023

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1

Zhao, Qun, Jin Zhang, and Michal Szostak. "Ruthenium(0)-sequential catalysis for the synthesis of sterically hindered amines by C–H arylation/hydrosilylation." Chemical Communications 55, no. 61 (2019): 9003–6. http://dx.doi.org/10.1039/c9cc04072b.

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2

Zhu, Xiaxia, and Haifeng Du. "A chiral borane catalyzed asymmetric hydrosilylation of imines." Organic & Biomolecular Chemistry 13, no. 4 (2015): 1013–16. http://dx.doi.org/10.1039/c4ob02419b.

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3

Pèrez-Miqueo, Jorge, Virginia San Nacianceno, F. Borja Urquiola, and Zoraida Freixa. "Revisiting the iridacycle-catalyzed hydrosilylation of enolizable imines." Catalysis Science & Technology 8, no. 24 (2018): 6316–29. http://dx.doi.org/10.1039/c8cy01236a.

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4

Li, Bin, Shilin Zhang, Weizhen Wu, Lecheng Liang, Shaohua Jiang, Lu Chen, and Yibiao Li. "Imidazolium-based ionic liquid-catalyzed hydrosilylation of imines and reductive amination of aldehydes using hydrosilane as the reductant." RSC Advances 7, no. 51 (2017): 31795–99. http://dx.doi.org/10.1039/c7ra04245k.

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5

Saini, Anu, Cecilia R. Smith, Francis S. Wekesa, Amanda K. Helms, and Michael Findlater. "Conversion of aldimines to secondary amines using iron-catalysed hydrosilylation." Organic & Biomolecular Chemistry 16, no. 48 (2018): 9368–72. http://dx.doi.org/10.1039/c8ob01262h.

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6

Yun, J., B. M. Park, and S. Mun. "Zinc-Catalyzed Enantioselective Hydrosilylation of Imines." Synfacts 2006, no. 9 (September 2006): 0928. http://dx.doi.org/10.1055/s-2006-949239.

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7

Park, Bu-Mahn, Soungyun Mun, and Jaesook Yun. "Zinc-Catalyzed Enantioselective Hydrosilylation of Imines." Advanced Synthesis & Catalysis 348, no. 9 (June 2006): 1029–32. http://dx.doi.org/10.1002/adsc.200606149.

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8

Li, Bin, Jean-Baptiste Sortais, and Christophe Darcel. "Amine synthesis via transition metal homogeneous catalysed hydrosilylation." RSC Advances 6, no. 62 (2016): 57603–25. http://dx.doi.org/10.1039/c6ra10494k.

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This review summarizes the preparation of amines involving homogeneous transition metal catalysed hydrosilylation including reductions of imines, amides, nitro and nitriles, reductive aminations and N-methylation of amines with CO₂.

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9

Zhou, Miao-Miao, Guanghui Chen, and Li Dang. "Enantioselective hydrosilylation of unsaturated carbon–heteroatom bonds (CN, CO) catalyzed by [Ru–S] complexes: a theoretical study." RSC Advances 10, no. 16 (2020): 9431–37. http://dx.doi.org/10.1039/c9ra10760f.

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A detailed theoretical study on the mechanism of enanthioselective hydrosilylation of imines and ketones catalyzed by the ruthenium(ii) thiolate catalyst with a chiral monodentate phosphine ligand is carried out in this work.

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10

Schneider, Jan, Eckhard Popowski, and Hans Fuhrmann. "Reaktionen von Lithiumhydridosilylamiden mit Carbonylverbindungen und Gemischen von Carbonylverbindungen und Chlortrimethylsilan / Reactions of Lithium Hydridosilylamides with Carbonyl Compounds and Mixtures of Carbonyl Compounds and Chlorotrimethylsilane." Zeitschrift für Naturforschung B 53, no. 7 (July 1, 1998): 663–72. http://dx.doi.org/10.1515/znb-1998-0703.

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Abstract The lithium hydridosilylamides Me2(H)SiN(Li)R (1: R = CMe3, 2: R = SiMe3) were allowed to react either with the non-enolizable carbonyl compounds CH2=C(Me)CHO, PhCHO and Ph2CO followed by trapping with chlorotrimethylsilane (A), or with mixtures of these carbonyl compounds and chlorotrimethylsilane (B). In the second case the course of the reactions is determined by the carbonyl compound. The composition of the reaction mixtures is nearly the same according to A and B.Main products in the reactions with the aldehydes are the corresponding imines R′CH=NR (R′ =CH2=C(Me), Ph) 3 , 4 , 8 ,9 formed by addition of the hydridosilylamides to the C = O group of the aldehydes and subsequent LiOSiMe2H elimination. Partial hydrosilylation of the aldehydes by the hydridosilanolate followed by the trimethylsilylation yields the alkoxydisiloxanes R'CH2OSiMe2OSiMe3 6 , 11. In some cases 2 partially reacts under hydrosilylation to give the alkoxydisilazanes R'CH2OSiMe2NHSiMe3 7,12.The hydrosilylation is the preferred reaction of 1 and 2 with benzophenone. The compounds Ph2CHOSiMe2NHR 13, 14 are obtained. This difference in the reaction behaviour of 1 and 2 towards the aldehydes and benzophenone is mainly due to steric reasons. Depending on the conditions the imines Ph2C=NR 20, 21 may be formed. Ph2CHOSiMe2OSiMe3 (22) is a secondary product of imine formation.In all reactions of 1 and 2 with the carbonyl compounds the corresponding alkoxysilanes R'CH2OSiMe3 (5: R' = CH2=C(Me), 6 : R' = Ph) and Ph2CHOSiMe3 (15) are generated.Compounds resulting from a reaction of 1 and 2 with chlorotrimethylsilane are produced to minor extent, but only if the molar ratio of amide to carbonyl compounds is not greater than one. The formation of a silanimine intermediate in reaction according to B is not observed.

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11

Sun, J., Z. Wang, M. Cheng, P. Wu, and S. Wei. "Organocatalytic Enantioselective Hydrosilylation of N-Aryl Imines." Synfacts 2006, no. 9 (September 2006): 0937. http://dx.doi.org/10.1055/s-2006-949219.

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12

Růžičková, Zdeňka, Roman Jambor, and Miroslav Novák. "Spontaneous Hydrosilylation of Substituted C=N Imines." European Journal of Inorganic Chemistry 2019, no. 28 (July 18, 2019): 3335–42. http://dx.doi.org/10.1002/ejic.201900516.

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13

Field, Leslie D., Barbara A. Messerle, and Sarah L. Rumble. "Iridium(I)-Catalysed Tandem Hydrosilylation-Protodesilylation of Imines." European Journal of Organic Chemistry 2005, no. 14 (July 2005): 2881–83. http://dx.doi.org/10.1002/ejoc.200500168.

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14

Takaki, Ken, Tohru Kamata, Yoshimi Miura, Tetsuya Shishido, and Katsuomi Takehira. "Dehydrogenative Silylation of Amines and Hydrosilylation of Imines Catalyzed by Ytterbium−Imine Complexes." Journal of Organic Chemistry 64, no. 11 (May 1999): 3891–95. http://dx.doi.org/10.1021/jo982154r.

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15

Park, Bu-Mahn, Xinhui Feng, and Jae-Sook Yun. "Enantioselective Hydrosilylation of Imines Catalyzed by Diamine-Zinc Complexes." Bulletin of the Korean Chemical Society 32, spc8 (August 20, 2011): 2960–64. http://dx.doi.org/10.5012/bkcs.2011.32.8.2960.

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16

Hansen, Marcus C., and Stephen L. Buchwald. "A Method for the Asymmetric Hydrosilylation ofN-Aryl Imines." Organic Letters 2, no. 5 (March 2000): 713–15. http://dx.doi.org/10.1021/ol005583w.

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17

Corre, Y., W. Iali, M. Hamdaoui, X. Trivelli, J. P. Djukic, F. Agbossou-Niedercorn, and C. Michon. "Efficient hydrosilylation of imines using catalysts based on iridium(iii) metallacycles." Catalysis Science & Technology 5, no. 3 (2015): 1452–58. http://dx.doi.org/10.1039/c4cy01233j.

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Ir(iii) metallacycles were applied as catalysts for the hydrosilylation of ketimines and aldimines by using sodium tetrakis[(3,5-trifluoromethyl)phenyl]borate, NaBArF₂₄, as an additive. By using a slight excess of the organosilane reagent, the reactions proceeded rapidly and efficiently, at low catalyst loadings and at room temperature.

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18

Takaki, Ken, Tohru Kamata, Yoshimi Miura, Tetsuya Shishido, and Katsuomi Takehira. "ChemInform Abstract: Dehydrogenative Silylation of Amines and Hydrosilylation of Imines Catalyzed by Ytterbium-Imine Complexes." ChemInform 30, no. 39 (June 13, 2010): no. http://dx.doi.org/10.1002/chin.199939147.

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19

Arena, Carmela. "Recent Progress in the Asymmetric Hydrosilylation of Ketones and Imines." Mini-Reviews in Organic Chemistry 6, no. 3 (August 1, 2009): 159–67. http://dx.doi.org/10.2174/157019309788922766.

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20

Bezłada, Agata, Marcin Szewczyk, and Jacek Mlynarski. "Enantioselective Hydrosilylation of Imines Catalyzed by Chiral Zinc Acetate Complexes." Journal of Organic Chemistry 81, no. 1 (December 18, 2015): 336–42. http://dx.doi.org/10.1021/acs.joc.5b02613.

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21

Zhu, Xiaxia, and Haifeng Du. "ChemInform Abstract: A Chiral Borane Catalyzed Asymmetric Hydrosilylation of Imines." ChemInform 46, no. 21 (May 2015): no. http://dx.doi.org/10.1002/chin.201521021.

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22

Hashimoto, Hisako, Ichihiro Aratani, Chizuko Kabuto, and Mitsuo Kira. "Stoichiometric Hydrosilylation of Nitriles and Catalytic Hydrosilylation of Imines and Ketones Using a μ-Silane Diruthenium Complex." Organometallics 22, no. 11 (May 2003): 2199–201. http://dx.doi.org/10.1021/om030219x.

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23

Díez-González, Silvia, and Steven P. Nolan. "TRANSITION METAL-CATALYZED HYDROSILYLATION OF CARBONYL COMPOUNDS AND IMINES. A REVIEW." Organic Preparations and Procedures International 39, no. 6 (December 2007): 523–59. http://dx.doi.org/10.1080/00304940709458641.

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24

Takei, Izuru, Yoshiaki Nishibayashi, Yasuyoshi Arikawa, Sakae Uemura, and Masanobu Hidai. "Iridium-Catalyzed Asymmetric Hydrosilylation of Imines Using Chiral Oxazolinyl-Phosphine Ligands." Organometallics 18, no. 11 (May 1999): 2271–74. http://dx.doi.org/10.1021/om981005w.

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25

Verdaguer, Xavier, Udo E. W. Lange, and Stephen L. Buchwald. "Amine Additives Greatly Expand the Scope of Asymmetric Hydrosilylation of Imines." Angewandte Chemie International Edition 37, no. 8 (May 4, 1998): 1103–7. http://dx.doi.org/10.1002/(sici)1521-3773(19980504)37:8<1103::aid-anie1103>3.0.co;2-m.

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26

Adamkiewicz, Anna, and Jacek Mlynarski. "Diastereoselective Hydrosilylation of N -(tert -Butylsulfinyl)imines Catalyzed by Zinc Acetate." European Journal of Organic Chemistry 2016, no. 5 (January 20, 2016): 1060–65. http://dx.doi.org/10.1002/ejoc.201501318.

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27

Hansen, Marcus C., and Stephen L. Buchwald. "ChemInform Abstract: A Method for the Asymmetric Hydrosilylation of N-Aryl Imines." ChemInform 31, no. 25 (June 7, 2010): no. http://dx.doi.org/10.1002/chin.200025046.

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28

Arena, Carmela G. "ChemInform Abstract: Recent Progress in the Asymmetric Hydrosilylation of Ketones and Imines." ChemInform 41, no. 24 (June 15, 2010): no. http://dx.doi.org/10.1002/chin.201024256.

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29

Szewczyk, Marcin, Agata Bezłada, and Jacek Mlynarski. "Zinc-Catalyzed Enantioselective Hydrosilylation of Ketones and Imines under Solvent-Free Conditions." ChemCatChem 8, no. 23 (November 9, 2016): 3575–79. http://dx.doi.org/10.1002/cctc.201601140.

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30

Khalimon, Andrey, Kristina Gudun, and Davit Hayrapetyan. "Base Metal Catalysts for Deoxygenative Reduction of Amides to Amines." Catalysts 9, no. 6 (May 28, 2019): 490. http://dx.doi.org/10.3390/catal9060490.

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The development of efficient methodologies for production of amines attracts significant attention from synthetic chemists, because amines serve as essential building blocks in the synthesis of many pharmaceuticals, natural products, and agrochemicals. In this regard, deoxygenative reduction of amides to amines by means of transition-metal-catalyzed hydrogenation, hydrosilylation, and hydroboration reactions represents an attractive alternative to conventional wasteful techniques based on stoichiometric reductions of the corresponding amides and imines, and reductive amination of aldehydes with metal hydride reagents. The relatively low electrophilicity of the amide carbonyl group makes this transformation more challenging compared to reduction of other carbonyl compounds, and the majority of the reported catalytic systems employ precious metals such as platinum, rhodium, iridium, and ruthenium. Despite the application of more abundant and environmentally benign base metal (Mn, Fe, Co, and Ni) complexes for deoxygenative reduction of amides have been developed to a lesser extent, such catalytic systems are of great importance. This review is focused on the current achievements in the base-metal-catalyzed deoxygenative hydrogenation, hydrosilylation, and hydroboration of amides to amines. Special attention is paid to the design of base metal catalysts and the mechanisms of such catalytic transformations.

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31

Riant, Olivier, Naouël Mostefaï, and James Courmarcel. "Recent Advances in the Asymmetric Hydrosilylation of Ketones, Imines and Electrophilic Double Bonds." Synthesis, no. 18 (2004): 2943–58. http://dx.doi.org/10.1055/s-2004-834932.

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32

Koller, Jürgen, and Robert G. Bergman. "Controlled Hydrosilylation of Carbonyls and Imines Catalyzed by a Cationic Aluminum Alkyl Complex." Organometallics 31, no. 7 (September 14, 2011): 2530–33. http://dx.doi.org/10.1021/om2008277.

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33

VERDAGUER, X., U. E. W. LANGE, and S. L. BUCHWALD. "ChemInform Abstract: Amine Additives Greatly Expand the Scope of Asymmetric Hydrosilylation of Imines." ChemInform 29, no. 31 (June 20, 2010): no. http://dx.doi.org/10.1002/chin.199831035.

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34

Castro, Luis C. Misal, Jean-Baptiste Sortais, and Christophe Darcel. "NHC-carbene cyclopentadienyl iron based catalyst for a general and efficient hydrosilylation of imines." Chem. Commun. 48, no. 1 (2012): 151–53. http://dx.doi.org/10.1039/c1cc14403k.

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35

Gajewy, Jadwiga, Jacek Gawronski, and Marcin Kwit. "Convenient, enantioselective hydrosilylation of imines in protic media catalyzed by a Zn-trianglamine complex." Organic & Biomolecular Chemistry 9, no. 10 (2011): 3863. http://dx.doi.org/10.1039/c1ob05074e.

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36

Gruber-Woelfler, Heidrun, Johannes G. Khinast, Michaela Flock, Roland C. Fischer, Jörg Sassmannshausen, Tsvetanka Stanoeva, and Georg Gescheidt. "Titanocene-Catalyzed Hydrosilylation of Imines: Experimental and Computational Investigations of the Catalytically Active Species." Organometallics 28, no. 8 (April 27, 2009): 2546–53. http://dx.doi.org/10.1021/om800643q.

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37

Bheeter, Linus P., Mickaël Henrion, Michael J. Chetcuti, Christophe Darcel, Vincent Ritleng, and Jean-Baptiste Sortais. "Cyclopentadienyl N-heterocyclic carbene–nickel complexes as efficient pre-catalysts for the hydrosilylation of imines." Catalysis Science & Technology 3, no. 12 (2013): 3111. http://dx.doi.org/10.1039/c3cy00514c.

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38

Li, Bin, Jean-Baptiste Sortais, Christophe Darcel, and Pierre H. Dixneuf. "Amine Synthesis through Mild Catalytic Hydrosilylation of Imines using Polymethylhydroxysiloxane and [RuCl2(arene)]2 Catalysts." ChemSusChem 5, no. 2 (February 3, 2012): 396–99. http://dx.doi.org/10.1002/cssc.201100585.

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39

Bories, Cassandre C., Marion Barbazanges, Etienne Derat, and Marc Petit. "Implication of a Silyl Cobalt Dihydride Complex as a Useful Catalyst for the Hydrosilylation of Imines." ACS Catalysis 11, no. 22 (November 10, 2021): 14262–73. http://dx.doi.org/10.1021/acscatal.1c03886.

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40

Misal Castro, Luis C., Jean-Baptiste Sortais, and Christophe Darcel. "ChemInform Abstract: NHC-Carbene Cyclopentadienyl Iron Based Catalyst for a General and Efficient Hydrosilylation of Imines." ChemInform 43, no. 16 (March 22, 2012): no. http://dx.doi.org/10.1002/chin.201216035.

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41

Yun, Jaesook, and Stephen L. Buchwald. "Efficient Kinetic Resolution in the Asymmetric Hydrosilylation of Imines of 3-Substituted Indanones and 4-Substituted Tetralones." Journal of Organic Chemistry 65, no. 3 (February 2000): 767–74. http://dx.doi.org/10.1021/jo991328h.

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42

Li, Bin, Charles B. Bheeter, Christophe Darcel, and Pierre H. Dixneuf. "Sequential Ruthenium(II)-Acetate Catalyzed C–H Bond Diarylation in NMP or Water and Hydrosilylation of Imines." Topics in Catalysis 57, no. 10-13 (March 4, 2014): 833–42. http://dx.doi.org/10.1007/s11244-014-0244-1.

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43

Hu, Xiao-Yan, Min-Min Zhang, Chang Shu, Yong-Hong Zhang, Li-Hua Liao, Wei-Cheng Yuan, and Xiao-Mei Zhang. "Enantioselective Lewis-Base-Catalyzed Asymmetric Hydrosilylation of Substituted BenzophenoneN-Aryl Imines: Efficient Synthesis of Chiral (Diarylmethyl)amines." Advanced Synthesis & Catalysis 356, no. 17 (October 13, 2014): 3539–44. http://dx.doi.org/10.1002/adsc.201400643.

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44

Pérez, Manuel, Zheng-Wang Qu, Christopher B. Caputo, Vitali Podgorny, Lindsay J. Hounjet, Andreas Hansen, Roman Dobrovetsky, Stefan Grimme, and Douglas W. Stephan. "Hydrosilylation of Ketones, Imines and Nitriles Catalysed by Electrophilic Phosphonium Cations: Functional Group Selectivity and Mechanistic Considerations." Chemistry - A European Journal 21, no. 17 (March 10, 2015): 6491–500. http://dx.doi.org/10.1002/chem.201406356.

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45

Mewald, Marius, and Martin Oestreich. "Illuminating the Mechanism of the Borane-Catalyzed Hydrosilylation of Imines with Both an Axially Chiral Borane and Silane." Chemistry - A European Journal 18, no. 44 (September 20, 2012): 14079–84. http://dx.doi.org/10.1002/chem.201202693.

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46

Wu, Pengcheng, Zhouyu Wang, Mounuo Cheng, Li Zhou, and Jian Sun. "Development of highly enantioselective new Lewis basic N-formamide organocatalysts for hydrosilylation of imines with an unprecedented substrate profile." Tetrahedron 64, no. 49 (December 2008): 11304–12. http://dx.doi.org/10.1016/j.tet.2008.09.034.

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47

Yun, Jaesook, and Stephen L. Buchwald. "ChemInform Abstract: Efficient Kinetic Resolution in the Asymmetric Hydrosilylation of Imines of 3-Substituted Indanones and 4-Substituted Tetralones." ChemInform 31, no. 23 (June 8, 2010): no. http://dx.doi.org/10.1002/chin.200023030.

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48

Li, Bin, Charles B. Bheeter, Christophe Darcel, and Pierre H. Dixneuf. "Sequential Catalysis for the Production of Sterically Hindered Amines: Ru(II)-Catalyzed C–H Bond Activation and Hydrosilylation of Imines." ACS Catalysis 1, no. 10 (August 24, 2011): 1221–24. http://dx.doi.org/10.1021/cs200331m.

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49

Gruber-Woelfler, Heidrun, Georg J. Lichtenegger, Christoph Neubauer, Eleonora Polo, and Johannes G. Khinast. "Tethered ansa-bridged titanium complexes immobilized on 3-mercaptopropyl-functionalized silica gel and their application for the hydrosilylation of imines." Dalton Transactions 41, no. 41 (2012): 12711. http://dx.doi.org/10.1039/c2dt31207g.

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50

Hu, Xiao-Yan, Min-Min Zhang, Chang Shu, Yong-Hong Zhang, Li-Hua Liao, Wei-Cheng Yuan, and Xiao-Mei Zhang. "ChemInform Abstract: Enantioselective Lewis-Base-Catalyzed Asymmetric Hydrosilylation of Substituted Benzophenone N-Aryl Imines: Efficient Synthesis of Chiral (Diarylmethyl)amines." ChemInform 46, no. 17 (April 2015): no. http://dx.doi.org/10.1002/chin.201517121.

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