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Journal articles on the topic 'Hydroformylation of Alkenes'

Author: Grafiati

Published: 6 September 2023

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1

Shi, Yukun, Yang Lu, Tongxin Ren, Jie Li, Qiqige Hu, Xiaojing Hu, Baolin Zhu, and Weiping Huang. "Rh Particles Supported on Sulfated g-C3N4: A Highly Efficient and Recyclable Heterogeneous Catalyst for Alkene Hydroformylation." Catalysts 10, no. 11 (November 23, 2020): 1359. http://dx.doi.org/10.3390/catal10111359.

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The hydroformylation of alkenes with CO and H2 to manufacture aldehydes is one of the most large-scale chemical reactions. However, an efficient and recyclable heterogeneous catalyst for alkene hydroformylation is extremely in demand in academia and industry. In this study, a sulfated carbon nitride supported rhodium particle catalyst (Rh/S-g-C3N4) was successfully synthesized via an impregnation-borohydride reduction method and applied in the hydroformylation of alkenes. The catalysts were characterized by XRD, FTIR, SEM, TEM, XPS, and nitrogen adsorption. The influence of the sulfate content, pressure of syngas, temperature, and reaction time, as well as the stability of Rh/S-g-C3N4, on the hydroformylation was examined in detail. The delocalized conjugated structure in g-C3N4 can lead to the formation of electron-deficient aromatic intermediates with alkenes. The sulphate g-C3N4 has a defected surface owing to the formation of oxygen vacancies, which increased the adsorption and dispersion of RhNPs on the surface of g-C3N4. Therefore, Rh/S-g-C3N4 exhibited an outstanding catalytic performance for styrene hydroformylation (TOF = 9000 h−1), the conversion of styrene could reach 99.9%, and the regioselectivity for the branched aldehyde was 52% under the optimized reaction conditions. The catalytic properties of Rh/S-g-C3N4 were also studied in the hydroformylation of various alkenes and displayed an excellent catalytic performance. Furthermore, the reuse of Rh/S-g-C3N4 was tested for five recycling processes, without an obvious decrease in the activity and selectivity under the optimum reaction conditions. These findings demonstrated that Rh/S-g-C3N4 is a potential catalyst for heterogeneous hydroformylation.

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2

Doyle, MM, WR Jackson, and P. Perlmutter. "The Stereochemistry of Organometallic Compounds. XXXIV. Regioselection in the Hydroformylation of Silylalkenes." Australian Journal of Chemistry 42, no. 11 (1989): 1907. http://dx.doi.org/10.1071/ch9891907.

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The regiochemistry of hydroformylation of alkenes can be controlled by the use of bulky silyl groups attached to the alkene. Use of the t-butyldiphenylsilyl group leads to almost total regiocontrol and the method has been applied to the synthesis of aldols.

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3

Hood, Drew M., Ryan A. Johnson, Alex E. Carpenter, Jarod M. Younker, David J. Vinyard, and George G. Stanley. "Highly active cationic cobalt(II) hydroformylation catalysts." Science 367, no. 6477 (January 30, 2020): 542–48. http://dx.doi.org/10.1126/science.aaw7742.

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The cobalt complexes HCo(CO)4 and HCo(CO)3(PR3) were the original industrial catalysts used for the hydroformylation of alkenes through reaction with hydrogen and carbon monoxide to produce aldehydes. More recent and expensive rhodium-phosphine catalysts are hundreds of times more active and operate under considerably lower pressures. Cationic cobalt(II) bisphosphine hydrido-carbonyl catalysts that are far more active than traditional neutral cobalt(I) catalysts and approach rhodium catalysts in activity are reported here. These catalysts have low linear-to-branched (L:B) regioselectivity for simple linear alkenes. However, owing to their high alkene isomerization activity and increased steric effects due to the bisphosphine ligand, they have high L:B selectivities for internal alkenes with alkyl branches. These catalysts exhibit long lifetimes and substantial resistance to degradation reactions.

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4

Yu, Xuetong, Yuxia Ji, Yan Jiang, Rui Lang, Yanxiong Fang, and Botao Qiao. "Recent Development of Single-Atom Catalysis for the Functionalization of Alkenes." Catalysts 13, no. 4 (April 12, 2023): 730. http://dx.doi.org/10.3390/catal13040730.

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The functionalization of alkenes is one of the most important conversions in synthetic chemistry to prepare numerous fine chemicals. Typical procedures, such as hydrosilylation and hydroformylation, are traditionally catalyzed using homogeneous noble metal complexes, while the highly reactive and stable heterogeneous single-atom catalysts (SACs) now provide alternative approaches to fulfill these conversions by combining the advantages of both homogeneous catalysts and heterogeneous nanoparticle catalysts. In this review, the recent achievement in single-atom catalyzed hydrosilylation and hydroformylation reactions are introduced, and we highlight the latest applications of SACs for additive reactions, constructing new C-Y (Y = B, P, S, N) bonds on the terminal carbon atoms of alkenes, and then mention the applications in single-metal-atom catalyzed hydrogenation and epoxidation reactions. We also note that some tandem reactions are conveniently realized in one pot by the concisely fabricated SACs, facilitating the preparation of some pharmaceutical compounds. Lastly, the challenges facing single-atom catalysis for alkene conversions are briefly mentioned.

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5

Geng, Hui-Qing, Tim Meyer, Robert Franke, and Xiao-Feng Wu. "Copper-catalyzed hydroformylation and hydroxymethylation of styrenes." Chemical Science 12, no. 44 (2021): 14937–43. http://dx.doi.org/10.1039/d1sc05474k.

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6

Peral, Daniel, Daniel Herrera, Julio Real, Teresa Flor, and J. Carles Bayón. "Strong π-acceptor sulfonated phosphines in biphasic rhodium-catalyzed hydroformylation of polar alkenes." Catalysis Science & Technology 6, no. 3 (2016): 800–808. http://dx.doi.org/10.1039/c5cy01004g.

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7

Chevry, M., T. Vanbésien, S. Menuel, E. Monflier, and F. Hapiot. "Tetronics/cyclodextrin-based hydrogels as catalyst-containing media for the hydroformylation of higher olefins." Catalysis Science & Technology 7, no. 1 (2017): 114–23. http://dx.doi.org/10.1039/c6cy02070d.

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8

Shi, Yukun, Gang Ji, Qiqige Hu, Yang Lu, Xiaojing Hu, Baolin Zhu, and Weiping Huang. "Highly uniform Rh nanoparticles supported on boron doped g-C3N4 as a highly efficient and recyclable catalyst for heterogeneous hydroformylation of alkenes." New Journal of Chemistry 44, no. 1 (2020): 20–23. http://dx.doi.org/10.1039/c9nj05385a.

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9

Wu, Lipeng, Qiang Liu, Anke Spannenberg, Ralf Jackstell, and Matthias Beller. "Highly regioselective osmium-catalyzed hydroformylation." Chemical Communications 51, no. 15 (2015): 3080–82. http://dx.doi.org/10.1039/c4cc05626d.

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Osmium carbonyl combined with 2-imidazoyl-substituted phosphine ligands forms active species for the highly regioselective and general hydroformylation of alkenes to produce aldehydes in good yields and excellent regioselectivities. An unusual phosphido bridged trinuclear osmium catalyst structure was obtained.

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10

Nandakumar, Avanashiappan, Manoj K. Sahoo, and Ekambaram Balaraman. "Reverse-hydroformylation: a missing reaction explored." Organic Chemistry Frontiers 2, no. 10 (2015): 1422–24. http://dx.doi.org/10.1039/c5qo00229j.

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Recent progress in transition-metal catalysed acceptor- and acceptorless-reverse hydroformylation of aldehydes for the conversion of olefins has been discussed. The aldehyde feedstock serves as a source for production of syngas and valuable alkenes.

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11

Krupčík, Ján, and Dušan Repka. "Analysis of hydroformylation products of higher n-alkenes by capillary gas chromatography." Collection of Czechoslovak Chemical Communications 50, no. 8 (1985): 1808–18. http://dx.doi.org/10.1135/cccc19851808.

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A mixture of alcohols obtained by hydroformylation of C10-C13 n-alkenes was analyzed by capillary gas chromatography using Carbowax 20M stationary phase, and acetates prepared from the alcohols were analyzed on capillary columns using Carbowax 20M and Apiezon L stationary phases. The capillary gas chromatography and gas chromatography-mass spectrometry treatment gave evidence that all of the 24 alcohols that could form by the hydroformylation reaction mechanism were present.

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12

Terhorst, M., C. Plass, A. Hinzmann, A. Guntermann, T. Jolmes, J. Rösler, D. Panke, et al. "One-pot synthesis of aldoximes from alkenes via Rh-catalysed hydroformylation in an aqueous solvent system." Green Chemistry 22, no. 22 (2020): 7974–82. http://dx.doi.org/10.1039/d0gc03141k.

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Aldoxime synthesis directly starting from alkenes was successfully achieved through the combination of hydroformylation and subsequent condensation of the aldehyde intermediate with aqueous hydroxylamine in a one-pot process.

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13

Bibouche, Bachir, Daniel Peral, Dmitrij Stehl, Viktor Söderholm, Reinhard Schomäcker, Regine von Klitzing, and Dieter Vogt. "Multiphasic aqueous hydroformylation of 1-alkenes with micelle-like polymer particles as phase transfer agents." RSC Advances 8, no. 41 (2018): 23332–38. http://dx.doi.org/10.1039/c8ra04022b.

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Micelle-like polyelectrolyte polymer particles were applied as phase transfer agents and catalyst carriers in the multiphasic hydroformylation of long chain alkenes achieving high turnover frequencies and efficient catalyst recovery.

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14

Kämper, Alexander, Peter Kucmierczyk, Thomas Seidensticker, Andreas J. Vorholt, Robert Franke, and Arno Behr. "Ruthenium-catalyzed hydroformylation: from laboratory to continuous miniplant scale." Catalysis Science & Technology 6, no. 22 (2016): 8072–79. http://dx.doi.org/10.1039/c6cy01374k.

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Ruthenium running its rounds – recycling of a homogeneous ruthenium catalyst for hydroformylation of linear aliphatic alkenes by ex situ product extraction and successful application in a continuously operated miniplant for 90 h.

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15

Imam, Hasan T., Amanda G. Jarvis, Veronica Celorrio, Irshad Baig, Christopher C. R. Allen, Andrew C. Marr, and Paul C. J. Kamer. "Catalytic and biophysical investigation of rhodium hydroformylase." Catalysis Science & Technology 9, no. 22 (2019): 6428–37. http://dx.doi.org/10.1039/c9cy01679a.

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Rh-Containing artificial metalloenzymes based on two mutants of sterol carrier protein_2L (SCP_2L) have been shown to act as hydroformylases, exhibiting significant activity and unexpectedly high selectivity in the hydroformylation of alkenes.

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16

Liu, Yan-li, Jian-gui Zhao, Yuan-jiang Zhao, Hui-Min Liu, Hai-yan Fu, Xue-li Zheng, Mao-lin Yuan, Rui-xiang Li, and Hua Chen. "Homogeneous hydroformylation of long chain alkenes catalyzed by water soluble phosphine rhodium complex in CH3OH and efficient catalyst cycling." RSC Advances 9, no. 13 (2019): 7382–87. http://dx.doi.org/10.1039/c8ra08787c.

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Hydroformylation of long-chain alkenes proceeded homogeneously in methanol efficiently. The catalyst could be separated heterogeneously when methanol was removed and recycled for four times without obvious loss in catalytic performance and rhodium.

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17

Takeuchi, Ryo, and Nobuhiro Sato. "Hydroformylation of alkenes having organosilicon substituents." Journal of Organometallic Chemistry 393, no. 1 (August 1990): 1–10. http://dx.doi.org/10.1016/0022-328x(90)87193-h.

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18

Kardasheva, Yulia, Maria Terenina, Daniil Sokolov, Natalia Sinikova, Sergey Kardashev, and Eduard Karakhanov. "Hydroformylation of Alkenes over Phosphorous-Free Rhodium Supported on N-Doped Silica." Catalysts 13, no. 5 (April 28, 2023): 818. http://dx.doi.org/10.3390/catal13050818.

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A new phosphorous-free rhodium supported on a nitrogen-doped silica was successfully used as a catalyst for the hydroformylation of alkenes. The obtained material and the catalyst were characterized by XRD, XPS, FTIR, SEM, TEM, ICP AES, and low-temperature nitrogen adsorption–desorption measurements. The catalytic performance was studied by the example of the hydroformylation of octene-1 at temperatures of 80–140 °C and a pressure of 5.0 MPa. The catalyst provided a 99% conversion of 1-octene with a 98% yield of aldehydes and showed a good conversion of styrene and cyclohexene. The catalyst can be repeatedly used in ten consecutive cycles, with its activity remaining constant.

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19

Zhang, Yang, Michel Sigrist, and Paweł Dydio. "Palladium‐Catalyzed Hydroformylation of Alkenes and Alkynes." European Journal of Organic Chemistry 2021, no. 44 (October 19, 2021): 5985–97. http://dx.doi.org/10.1002/ejoc.202101020.

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20

Reek, J., M. Kuil, T. Soltner, and P. van Leeuwen. "Hydroformylation of Internal Alkenes by Encapsulated Rhodium." Synfacts 2006, no. 12 (December 2006): 1262. http://dx.doi.org/10.1055/s-2006-949501.

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21

Sharma, Sumeet K., and Raksh V. Jasra. "Aqueous phase catalytic hydroformylation reactions of alkenes." Catalysis Today 247 (June 2015): 70–81. http://dx.doi.org/10.1016/j.cattod.2014.07.059.

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22

Cocq, Aurélien, Hervé Bricout, Florence Djedaïni-Pilard, Sébastien Tilloy, and Eric Monflier. "Rhodium-Catalyzed Aqueous Biphasic Olefin Hydroformylation Promoted by Amphiphilic Cyclodextrins." Catalysts 10, no. 1 (January 1, 2020): 56. http://dx.doi.org/10.3390/catal10010056.

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Hydroformylation is an industrial process that allows for the production of aldehydes from alkenes using transition metals. The reaction can be carried out in water, and the catalyst may be recycled at the end of the reaction. The industrial application of rhodium-catalyzed aqueous hydroformylation has been demonstrated for smaller olefins (propene and butene). Unfortunately, larger olefins are weakly soluble in water, which results in very low catalytic activity. In an attempt to counteract this, we investigated the use of amphiphilic oleic succinyl-cyclodextrins (OS-CDs) synthesized from oleic acid derivatives and maleic anhydride. OS-CDs were found to increase the catalytic activity of rhodium during the hydroformylation of water-insoluble olefins, such as 1-decene and 1-hexadecene, by promoting mass transfer. Recyclability of the catalytic system was also evaluated in the presence of these cyclodextrins.

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23

Zhang, Xiaoli, Juan Wei, and Xiaoming Zhang. "Encapsulated liquid nano-droplets for efficient and selective biphasic hydroformylation of long-chain alkenes." New Journal of Chemistry 43, no. 35 (2019): 14134–38. http://dx.doi.org/10.1039/c9nj02493j.

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24

Jackson, W. Roy, Patrick Parlmutter, and Guem-Hee Suh. "Chelation control in the hydroformylation of terminal alkenes." Journal of the Chemical Society, Chemical Communications, no. 10 (1987): 724. http://dx.doi.org/10.1039/c39870000724.

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25

Tao, Lin, Mingmei Zhong, Jian Chen, Sanjeevi Jayakumar, Lina Liu, He Li, and Qihua Yang. "Heterogeneous hydroformylation of long-chain alkenes in IL-in-oil Pickering emulsion." Green Chemistry 20, no. 1 (2018): 188–96. http://dx.doi.org/10.1039/c7gc02574b.

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An IL-in-oil Pickering emulsion prepared with Rh-sulfo-xantphos as the catalyst and dendritic mesoporous silica nanospheres as the stabilizer could efficiently catalyze the hydroformylation of 1-dodecene to afford TOF as high as 413 h⁻¹.

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26

Meyer, Wolfgang H., Richard J. Bowen, and David G. Billing. "Tri(3-pyridyl)phosphine as Amphiphilic Ligand in the Rhodium-catalysed Hydroformylation of 1-Hexene." Zeitschrift für Naturforschung B 62, no. 3 (March 1, 2007): 339–45. http://dx.doi.org/10.1515/znb-2007-0306.

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The molecular structure of carbonylchlorobis(tri(3-pyridyl)phosphine)rhodium, 1, has been determined by X-ray diffraction methods. The N-protonated trifluoromethanesulfonate (triflate) complex 3 was synthesised as a model compound for the extraction of a rhodium complex bearing amphiphilic ligands which can allow catalyst recycling in the hydroformylation of alkenes by using their distribution behavior in organic and aqueous solvents of different pH. The high water-solubility of the employed ligand renders the recycling method as only partly successful due to insufficient extraction from the water phase into the organic phase. In the hydroformylation of 1-hexene the production of n-heptanal is slightly disfavoured when using the ligand tri(3-pyridyl)phosphine as compared to triphenylphosphine which can be ascribed to a higher amount of ligand-deficient active rhodium complexes of the less basic pyridyl phosphine ligand under CO pressure.

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27

Breit, Bernhard, and Wolfgang Seiche. "Self-assembly of bidentate ligands for combinatorial homogeneous catalysis based on an A-T base pair model." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 249–56. http://dx.doi.org/10.1351/pac200678020249.

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A new concept for generation of chelating ligand libraries for homogeneous metal complex catalysis based on self-assembly is presented. Thus, self-assembly of structurally simple monodentate ligands in order to give structurally more complex bidentate ligands is achieved employing hydrogen bonding. Based on this concept and on the 2-pyridone/hydroxypyridine tautomeric system, a new rhodium catalyst was identified which operated with excellent activity and regioselectivity upon hydroformylation of terminal alkenes. In order to generate defined unsymmetrical heterodimeric ligands, an A-T base pair analog-the aminopyridine/isoquinolone system-was developed which allows for complementary hydrogen bonding. Based on this platform, a 4 x 4 phosphine ligand library was screened in the course of the rhodium-catalyzed hydroformylation of 1-octene. A catalyst operating with outstanding activity and regioselectivity in favor of the linear aldehyde was discovered.

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28

Adams, Dave J., James A. Bennett, David J. Cole-Hamilton, Eric G. Hope, Jonathan Hopewell, Jo Kight, Peter Pogorzelec, and Alison M. Stuart. "Rhodium catalysed hydroformylation of alkenes using highly fluorophilic phosphines." Dalton Transactions, no. 24 (2005): 3862. http://dx.doi.org/10.1039/b510766k.

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29

Desset, Simon L., Simon W. Reader, and David J. Cole-Hamilton. "Aqueous-biphasic hydroformylation of alkenes promoted by “weak” surfactants." Green Chemistry 11, no. 5 (2009): 630. http://dx.doi.org/10.1039/b822139a.

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30

Watkins, Avery L., Brian G. Hashiguchi, and Clark R. Landis. "Highly Enantioselective Hydroformylation of Aryl Alkenes with Diazaphospholane Ligands." Organic Letters 10, no. 20 (October 16, 2008): 4553–56. http://dx.doi.org/10.1021/ol801723a.

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31

Tominaga, Ken-ichi, and Yoshiyuki Sasaki. "Ruthenium complex-catalyzed hydroformylation of alkenes with carbon dioxide." Catalysis Communications 1, no. 1-4 (November 2000): 1–3. http://dx.doi.org/10.1016/s1566-7367(00)00006-6.

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32

Achonduh, George, Qian Yang, and Howard Alper. "From alkenes to alcohols by cobalt-catalyzed hydroformylation–reduction." Tetrahedron 71, no. 8 (February 2015): 1241–46. http://dx.doi.org/10.1016/j.tet.2015.01.006.

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33

MacDougall, Joanna K., and David J. Cole-Hamilton. "Alcohols as sources of hydrogen in hydroformylation of alkenes." Polyhedron 9, no. 9 (January 1990): 1235–36. http://dx.doi.org/10.1016/s0277-5387(00)86901-6.

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34

Webb, Paul B., Thulani E. Kunene, and David J. Cole-Hamilton. "Continuous flow homogeneous hydroformylation of alkenes using supercritical fluids." Green Chemistry 7, no. 5 (2005): 373. http://dx.doi.org/10.1039/b416713a.

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35

Murzin, Dmitry Yu, Andreas Bernas, and Tapio Salmi. "Kinetic modelling of regioselectivity in alkenes hydroformylation over rhodium." Journal of Molecular Catalysis A: Chemical 315, no. 2 (January 15, 2010): 148–54. http://dx.doi.org/10.1016/j.molcata.2009.06.023.

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36

Sharma, Sumeet K., and Raksh V. Jasra. "ChemInform Abstract: Aqueous Phase Catalytic Hydroformylation Reactions of Alkenes." ChemInform 46, no. 21 (May 2015): no. http://dx.doi.org/10.1002/chin.201521286.

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37

Buhling, Armin, Paul C. J. Kamer, and Piet W. N. M. van Leeuwen. "Rhodium catalysed hydroformylation of higher alkenes using amphiphilic ligands." Journal of Molecular Catalysis A: Chemical 98, no. 2 (May 1995): 69–80. http://dx.doi.org/10.1016/1381-1169(95)00014-3.

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38

Fuchs, Evelyn, Manfred Keller, and Bernhard Breit. "Phosphabarrelenes as Ligands in Rhodium-Catalyzed Hydroformylation of Internal Alkenes Essentially Free of Alkene Isomerization." Chemistry - A European Journal 12, no. 26 (September 6, 2006): 6930–39. http://dx.doi.org/10.1002/chem.200600180.

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39

Desset, Simon L., David J. Cole-Hamilton, and Douglas F. Foster. "Aqueous-biphasic hydroformylation of higher alkenes promoted by alkylimidazolium salts." Chemical Communications, no. 19 (2007): 1933. http://dx.doi.org/10.1039/b618785d.

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40

Wildt, Julia, Anna C. Brezny, and Clark R. Landis. "Backbone-Modified Bisdiazaphospholanes for Regioselective Rhodium-Catalyzed Hydroformylation of Alkenes." Organometallics 36, no. 16 (August 16, 2017): 3142–51. http://dx.doi.org/10.1021/acs.organomet.7b00475.

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41

Deng, Yuchao, Hui Wang, Yuhan Sun, and Xiao Wang. "Principles and Applications of Enantioselective Hydroformylation of Terminal Disubstituted Alkenes." ACS Catalysis 5, no. 11 (October 20, 2015): 6828–37. http://dx.doi.org/10.1021/acscatal.5b01300.

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42

Rosales, Merlin, Angel González, Beatríz González, Cristhina Moratinos, Homero Pérez, Johán Urdaneta, and Roberto A. Sánchez-Delgado. "Hydroformylation of alkenes with paraformaldehyde catalyzed by rhodium–phosphine complexes." Journal of Organometallic Chemistry 690, no. 12 (June 2005): 3095–98. http://dx.doi.org/10.1016/j.jorganchem.2005.03.032.

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43

Yu, Zhiyong, Meredith S. Eno, Alexandra H. Annis, and James P. Morken. "Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand." Organic Letters 17, no. 13 (June 19, 2015): 3264–67. http://dx.doi.org/10.1021/acs.orglett.5b01421.

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44

Polas, Anastasios, James D. E. T. Wilton-Ely, Alexandra M. Z. Slawin, Douglas F. Foster, Petrus J. Steynberg, Michael J. Green, and David J. Cole-Hamilton. "Limonene-derived phosphines in the cobalt-catalysed hydroformylation of alkenes." Dalton Transactions, no. 24 (2003): 4669. http://dx.doi.org/10.1039/b310233e.

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45

Pedrós, Marta Giménez, Anna M. Masdeu-Bultó, Jerome Bayardon, and Denis Sinou. "Hydroformylation of Alkenes with Rhodium Catalyst in Supercritical Carbon Dioxide." Catalysis Letters 107, no. 3-4 (March 2006): 205–8. http://dx.doi.org/10.1007/s10562-005-0005-7.

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46

Yamane, Motoki, Noriaki Yukimura, Hiroshi Ishiai, and Koichi Narasaka. "Hydroformylation of Monosubstituted Alkenes Catalyzed by W–Rh Bimetallic Complex." Chemistry Letters 35, no. 5 (May 2006): 540–41. http://dx.doi.org/10.1246/cl.2006.540.

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47

Kamer, Paul C. J., Annemiek van Rooy, Gerard C. Schoemaker, and Piet W. N. M. van Leeuwen. "In situ mechanistic studies in rhodium catalyzed hydroformylation of alkenes." Coordination Chemistry Reviews 248, no. 21-24 (December 2004): 2409–24. http://dx.doi.org/10.1016/j.ccr.2004.06.006.

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48

Illesinghe, Jayamini, Eva M. Campi, W. Roy Jackson, and Andrea J. Robinson. "Synthesis of Nitrogen Heterocycles by Rhodium-Catalyzed Hydroformylation of Polymer-Attached Amino Alkenes with Syngas." Australian Journal of Chemistry 57, no. 6 (2004): 531. http://dx.doi.org/10.1071/ch03269.

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Rhodium(I) phosphite catalyzed hydroaminomethylation of resin-tethered amino alkenes with H2/CO gives moderate to good yields of five-, eight-, ten-, and thirteen-membered heterocycles. Competing hydrogenation, dimerization, or polymerization reactions were not observed using this methodology.

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49

Obrecht, Lorenz, Paul C. J. Kamer, and Wouter Laan. "Alternative approaches for the aqueous–organic biphasic hydroformylation of higher alkenes." Catal. Sci. Technol. 3, no. 3 (2013): 541–51. http://dx.doi.org/10.1039/c2cy20538f.

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50

Dingwall, Paul, José A. Fuentes, Luke Crawford, Alexandra M. Z. Slawin, Michael Bühl, and Matthew L. Clarke. "Understanding a Hydroformylation Catalyst that Produces Branched Aldehydes from Alkyl Alkenes." Journal of the American Chemical Society 139, no. 44 (October 25, 2017): 15921–32. http://dx.doi.org/10.1021/jacs.7b09164.

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