Journal articles: 'Difunctionnalization of internal olefins'

1

Seayad, A. "Internal Olefins to Linear Amines." Science 297, no. 5587 (September 6, 2002): 1676–78. http://dx.doi.org/10.1126/science.1074801.

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2

Brändli, Christof, and Thomas R Ward. "Librariesvia Metathesis of Internal Olefins." Helvetica Chimica Acta 81, no. 9 (September 9, 1998): 1616–21. http://dx.doi.org/10.1002/(sici)1522-2675(19980909)81:9<1616::aid-hlca1616>3.0.co;2-p.

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3

Maity, Soham, Pravas Dolui, Rajesh Kancherla, and Debabrata Maiti. "Introducing unactivated acyclic internal aliphatic olefins into a cobalt catalyzed allylic selective dehydrogenative Heck reaction." Chemical Science 8, no. 7 (2017): 5181–85. http://dx.doi.org/10.1039/c7sc01204g.

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A highly regio- and stereoselective cobalt catalyzed allylic selective dehydrogenative Heck reaction with internal aliphatic olefins was developed. Both internal and terminal aliphatic olefins can be employed, thereby significantly expanding the scope of alkenylation chemistry.

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4

Weliange, Nandita M., David S. McGuinness, Michael G. Gardiner, and Jim Patel. "Insertion, elimination and isomerisation of olefins at alkylaluminium hydride: an experimental and theoretical study." Dalton Transactions 44, no. 34 (2015): 15286–96. http://dx.doi.org/10.1039/c5dt00955c.

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5

Roberts, D., and D. Williams. "Why Internal Olefins are difficult to Sulphonate." Tenside Surfactants Detergents 22, no. 4 (July 1, 1985): 193–95. http://dx.doi.org/10.1515/tsd-1985-220408.

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6

Wu, Ping, Fei Huang, Jiang Lou, Quannan Wang, Zhuqing Liu, and Zhengkun Yu. "Brønsted acid-catalyzed phenylselenenylation of internal olefins." Tetrahedron Letters 56, no. 19 (May 2015): 2488–91. http://dx.doi.org/10.1016/j.tetlet.2015.03.096.

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7

Yoshimura, Haruo, Yoshihisa Endo, and Shigeru Hashimoto. "NMR study on sulfonation of internal olefins." Journal of the American Oil Chemists Society 68, no. 8 (August 1991): 623–28. http://dx.doi.org/10.1007/bf02660166.

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8

Ternel, Jérémy, Bastien Léger, Eric Monflier, and Frédéric Hapiot. "Amines as effective ligands in iridium-catalyzed decarbonylative dehydration of biosourced substrates." Catalysis Science & Technology 8, no. 15 (2018): 3948–53. http://dx.doi.org/10.1039/c8cy00621k.

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9

Zhu, Cheng-Liang, Jun-Shan Tian, Zhen-Yuan Gu, Guo-Wen Xing, and Hao Xu. "Iron(ii)-catalyzed asymmetric intramolecular olefin aminochlorination using chloride ion." Chemical Science 6, no. 5 (2015): 3044–50. http://dx.doi.org/10.1039/c5sc00221d.

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10

Wen, Jiangwei, Longfei Zhang, Xiaoting Yang, Cong Niu, Shuangfeng Wang, Wei Wei, Xuejun Sun, Jianjing Yang, and Hua Wang. "H2O-controlled selective thiocyanation and alkenylation of ketene dithioacetals under electrochemical oxidation." Green Chemistry 21, no. 13 (2019): 3597–601. http://dx.doi.org/10.1039/c9gc01351b.

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Efficient and H₂O-controlled selective thiocyanation and alkenylation of internal olefins, to afford tetrasubstituted olefins under electrochemical oxidation, has been successfully developed.

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11

Chevella, Durgaiah, Arun Kumar Macharla, Srujana Kodumuri, Rammurthy Banothu, Krishna Sai Gajula, Vasu Amrutham, Grigor'eva Nellya Gennadievna, and Narender Nama. "Synthesis of internal olefins by direct coupling of alcohols and olefins over Moβ zeolite." Catalysis Communications 123 (April 2019): 114–18. http://dx.doi.org/10.1016/j.catcom.2019.01.027.

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12

BRAENDLI, C., and T. R. WARD. "ChemInform Abstract: Libraries via Metathesis of Internal Olefins." ChemInform 29, no. 51 (June 18, 2010): no. http://dx.doi.org/10.1002/chin.199851051.

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13

Nelson, Taylor A. F., and Simon B. Blakey. "Intermolecular Allylic C−H Etherification of Internal Olefins." Angewandte Chemie 130, no. 45 (October 15, 2018): 15127–31. http://dx.doi.org/10.1002/ange.201809863.

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14

Nelson, Taylor A. F., and Simon B. Blakey. "Intermolecular Allylic C−H Etherification of Internal Olefins." Angewandte Chemie International Edition 57, no. 45 (October 15, 2018): 14911–15. http://dx.doi.org/10.1002/anie.201809863.

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15

Ma, Wangjing, Xiao TC, Liu BN, Xu ZC, Jin ZQ, and Gong QT. "12-Tungstophosphate Acids: An Efficient, Green and Recyclable Photocatalyst in Carbon-Carbon Double Bond Isomerization on Linear Alpha Olefins." Journal of Biomedical Research & Environmental Sciences 2, no. 11 (December 2021): 1170–75. http://dx.doi.org/10.37871/jbres1367.

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The accelerated UV visible photocatalytic carbon-carbon double bond isomerization of Linear Alpha Olefins (LAO) with 12-Tungstophosphate Acids (12-TPA) as an efficient, environmentally-friendly and recyclable catalyst was described, which produced the corresponding Linear Internal Olefins (LIO) in general high selectivity and high yields.

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16

Miller, D. G., and D. D. M. Wayner. "Electrode-mediated Wacker oxidation of cyclic and internal olefins." Canadian Journal of Chemistry 70, no. 9 (September 1, 1992): 2485–90. http://dx.doi.org/10.1139/v92-314.

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An improved method for the electrode-mediated oxidations of olefins by palladium(II) is described. Current efficiencies from 80% to 95% were obtained in oxidations of 1-decene, styrene, trans-2-octene, and cyclohexene in which perchloric acid was added to a chloride-free solution of a palladium(II) acetate catalyst. The palladium(0) was reoxidized to palladium(II) by reaction with catalytic amounts of benzoquinone, which was, in turn, regenerated by anodic oxidation. Addition of varying amounts of perchloric acid did not affect the current efficiency but accelerated the oxidation reaction, up to a concentration of approximately 0.15 M. The current efficiency remained high (>80%) over the course of the electrode-mediated oxidations of 1-decene, trans-2-octene, and cyclohexene. At the end of the reactions, when the substrate was depleted, a drastic decrease in the current was observed, indicating that the catalytic cycle leading to product was primarily responsible for the electrochemical reaction. It also was shown that the rates of the electrochemical reactions were generally slower than those of homogeneous reactions in which a stoichiometric amount of benzoquinone was used, indicating that the electrochemical regeneration of benzoquinone was mass transport limited at the highest concentrations of perchloric acid. This is in contrast to other reports in the literature that suggested that the homogeneous (non-electrochemical) reactions were actually slower. Reasons for the discrepancy between these results are discussed.

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17

Beller, Matthias, and Jürgen G. E. Krauter. "Cobalt-catalyzed biphasic hydroformylation of internal short chain olefins." Journal of Molecular Catalysis A: Chemical 143, no. 1-3 (July 1999): 31–39. http://dx.doi.org/10.1016/s1381-1169(98)00360-4.

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18

Deng, Chao, Hua-Kui Liu, Zhong-Bo Zheng, Lijia Wang, Xiang Yu, Weihua Zhang, and Yong Tang. "Copper-Catalyzed Enantioselective Cyclopropanation of Internal Olefins with Diazomalonates." Organic Letters 19, no. 21 (October 24, 2017): 5717–19. http://dx.doi.org/10.1021/acs.orglett.7b02694.

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19

Klein, Holger, Ralf Jackstell, and Matthias Beller. "Synthesis of linear aldehydes from internal olefins in water." Chemical Communications, no. 17 (2005): 2283. http://dx.doi.org/10.1039/b418350a.

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20

Wu, Ping, Fei Huang, Jiang Lou, Quannan Wang, Zhuqing Liu, and Zhengkun Yu. "ChemInform Abstract: Broensted Acid-Catalyzed Phenylselenenylation of Internal Olefins." ChemInform 46, no. 34 (August 2015): no. http://dx.doi.org/10.1002/chin.201534227.

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21

de Klerk, Arno, Siphamandla W. Hadebe, Jude R. Govender, Deo Jaganyi, Andile B. Mzinyati, Ross S. Robinson, and Nontokozo Xaba. "Linear α-Olefins from Linear Internal Olefins by a Boron-Based Continuous Double-Bond Isomerization Process." Industrial & Engineering Chemistry Research 46, no. 2 (January 2007): 400–410. http://dx.doi.org/10.1021/ie060476c.

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22

Weliange, Nandita M., David S. McGuinness, Michael G. Gardiner, and Jim Patel. "Cobalt-bis(imino)pyridine complexes as catalysts for hydroalumination–isomerisation of internal olefins." Dalton Transactions 45, no. 26 (2016): 10842–49. http://dx.doi.org/10.1039/c6dt01113f.

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23

Zhang, Zongpeng, Caiyou Chen, Qian Wang, Zhengyu Han, Xiu-Qin Dong, and Xumu Zhang. "New tetraphosphite ligands for regioselective linear hydroformylation of terminal and internal olefins." RSC Advances 6, no. 18 (2016): 14559–62. http://dx.doi.org/10.1039/c5ra23683e.

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24

Chen, Caiyou, Pan Li, Zhoumi Hu, Heng Wang, Huaisu Zhu, Xinquan Hu, Yan Wang, Hui Lv, and Xumu Zhang. "Synthesis and application of a new triphosphorus ligand for regioselective linear hydroformylation: a potential way for the stepwise replacement of PPh3 for industrial use." Org. Chem. Front. 1, no. 8 (2014): 947–51. http://dx.doi.org/10.1039/c4qo00132j.

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25

Liu, Zhuqing, Fei Huang, Jiang Lou, Quannan Wang, and Zhengkun Yu. "Copper-promoted direct C–H alkoxylation of S,S-functionalized internal olefins with alcohols." Organic & Biomolecular Chemistry 15, no. 26 (2017): 5535–40. http://dx.doi.org/10.1039/c7ob01234a.

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26

Żak, P., M. Bołt, M. Kubicki, and C. Pietraszuk. "Highly selective hydrosilylation of olefins and acetylenes by platinum(0) complexes bearing bulky N-heterocyclic carbene ligands." Dalton Transactions 47, no. 6 (2018): 1903–10. http://dx.doi.org/10.1039/c7dt04392a.

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27

Yang, Yang, Shi-Liang Shi, Dawen Niu, Peng Liu, and Stephen L. Buchwald. "Catalytic asymmetric hydroamination of unactivated internal olefins to aliphatic amines." Science 349, no. 6243 (July 2, 2015): 62–66. http://dx.doi.org/10.1126/science.aab3753.

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Catalytic assembly of enantiopure aliphatic amines from abundant and readily available precursors has long been recognized as a paramount challenge in synthetic chemistry. Here, we describe a mild and general copper-catalyzed hydroamination that effectively converts unactivated internal olefins—an important yet unexploited class of abundant feedstock chemicals—into highly enantioenriched α-branched amines (≥96% enantiomeric excess) featuring two minimally differentiated aliphatic substituents. This method provides a powerful means to access a broad range of advanced, highly functionalized enantioenriched amines of interest in pharmaceutical research and other areas.

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28

Nakashima, Yusei, Goki Hirata, Tom D. Sheppard, and Takashi Nishikata. "The Mizoroki‐Heck Reaction with Internal Olefins: Reactivities and Stereoselectivities." Asian Journal of Organic Chemistry 9, no. 4 (February 14, 2020): 480–91. http://dx.doi.org/10.1002/ajoc.201900741.

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29

She, Yuan, Shuyu Zhang, and Le Wang. "Advances in Selective Allylic C—H Amination of Internal Olefins." Chinese Journal of Organic Chemistry 45, no. 2 (2025): 531. https://doi.org/10.6023/cjoc202407007.

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30

Mola, Laura, Mireia Sidera, and Stephen P. Fletcher. "Asymmetric Remote C–H Functionalization: Use of Internal Olefins in Tandem Hydrometallation–Isomerization–Asymmetric Conjugate Addition Sequences." Australian Journal of Chemistry 68, no. 3 (2015): 401. http://dx.doi.org/10.1071/ch14556.

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We describe catalytic asymmetric C–C formation using terminal alkyl-metal nucleophiles generated from internal olefins through a ‘chain-walking’ isomerization mechanism. Hydrometallation of internal olefins with the Schwartz reagent gives the least hindered alkyl-zirconocene after thermal (60°C in THF) isomerization. After switching the solvent from THF to dichloromethane, the alkyl-zirconocenes can be used in copper-catalyzed asymmetric conjugate additions. Addition to a variety of cyclic α,β-unsaturated species were achieved in modest (22–50 %) yield with high (84–92 % ee) enantioselectivity. This work demonstrates that remote C–H functionalization coupled with asymmetric C–C bond formation is possible, but the present procedures are limited in terms of yield and olefin scope.

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31

Wang, Xing, Junfeng Qian, Zhonghua Sun, Zhihui Zhang, and Mingyang He. "Synthesis, characterization, and functional evaluation of branched dodecyl phenol polyoxyethylene ethers: a novel class of surfactants with excellent wetting properties." RSC Advances 11, no. 60 (2021): 38054–59. http://dx.doi.org/10.1039/d1ra06873c.

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32

Weliange, Nandita M., David S. McGuinness, Michael G. Gardiner, and Jim Patel. "Insertion and isomerisation of internal olefins at alkylaluminium hydride: catalysis with zirconocene dichloride." Dalton Transactions 44, no. 46 (2015): 20098–107. http://dx.doi.org/10.1039/c5dt03257a.

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The insertion of internal olefins and chain walking isomerisation at di-n-octylaluminium hydride [Al(Oct)₂H], promoted by zirconocene dichloride [Cp₂ZrCl₂] has been studied.

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33

Song, Lijuan, Qiang Feng, Yong Wang, Shengtao Ding, Yun-Dong Wu, Xinhao Zhang, Lung Wa Chung, and Jianwei Sun. "Ru-Catalyzed Migratory Geminal Semihydrogenation of Internal Alkynes to Terminal Olefins." Journal of the American Chemical Society 141, no. 43 (October 9, 2019): 17441–51. http://dx.doi.org/10.1021/jacs.9b09658.

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34

Yan, Yongjun, Xiaowei Zhang, and Xumu Zhang. "A Tetraphosphorus Ligand for Highly Regioselective Isomerization−Hydroformylation of Internal Olefins." Journal of the American Chemical Society 128, no. 50 (December 2006): 16058–61. http://dx.doi.org/10.1021/ja0622249.

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35

Miller, D. G., and Danial D. M. Wayner. "Improved method for the Wacker oxidation of cyclic and internal olefins." Journal of Organic Chemistry 55, no. 9 (April 1990): 2924–27. http://dx.doi.org/10.1021/jo00296a067.

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36

MILLER, D. G., and D. D. M. WAYNER. "ChemInform Abstract: Electrode-Mediated Wacker Oxidation of Cyclic and Internal Olefins." ChemInform 24, no. 14 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199314098.

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37

Morandi, Bill, Zachary K. Wickens, and Robert H. Grubbs. "Practical and General Palladium-Catalyzed Synthesis of Ketones from Internal Olefins." Angewandte Chemie 125, no. 10 (January 16, 2013): 3016–20. http://dx.doi.org/10.1002/ange.201209541.

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38

Kumar, Ravi, Vikas Dwivedi, and Maddi Sridhar Reddy. "Metal-Free Iodosulfonylation of Internal Alkynes: Stereodefined Access to Tetrasubstituted Olefins." Advanced Synthesis & Catalysis 359, no. 16 (August 10, 2017): 2847–56. http://dx.doi.org/10.1002/adsc.201700576.

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39

van der Veen, Lars A., Paul C. J. Kamer, and Piet W. N. M. van Leeuwen. "Hydroformylation of Internal Olefins to Linear Aldehydes with Novel Rhodium Catalysts." Angewandte Chemie International Edition 38, no. 3 (February 1, 1999): 336–38. http://dx.doi.org/10.1002/(sici)1521-3773(19990201)38:3<336::aid-anie336>3.0.co;2-p.

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40

Morandi, Bill, Zachary K. Wickens, and Robert H. Grubbs. "Practical and General Palladium-Catalyzed Synthesis of Ketones from Internal Olefins." Angewandte Chemie International Edition 52, no. 10 (January 16, 2013): 2944–48. http://dx.doi.org/10.1002/anie.201209541.

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41

Hahn, Christine, Maria E. Cucciolito, and Aldo Vitagliano. "Coordinated Olefins as Incipient Carbocations: Catalytic Codimerization of Ethylene and Internal Olefins by a Dicationic Pt(II)−Ethylene Complex." Journal of the American Chemical Society 124, no. 31 (August 2002): 9038–39. http://dx.doi.org/10.1021/ja0263386.

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42

Scharnagl, Florian Korbinian, Maximilian Franz Hertrich, Francesco Ferretti, Carsten Kreyenschulte, Henrik Lund, Ralf Jackstell, and Matthias Beller. "Hydrogenation of terminal and internal olefins using a biowaste-derived heterogeneous cobalt catalyst." Science Advances 4, no. 9 (September 2018): eaau1248. http://dx.doi.org/10.1126/sciadv.aau1248.

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Hydrogenation of olefins is achieved using biowaste-derived cobalt chitosan catalysts. Characterization of the optimal Co@Chitosan-700 by STEM (scanning transmission electron microscopy), EELS (electron energy loss spectroscopy), PXRD (powder x-ray diffraction), and elemental analysis revealed the formation of a distinctive magnetic composite material with high metallic Co content. The general performance of this catalyst is demonstrated in the hydrogenation of 50 olefins including terminal, internal, and functionalized derivatives, as well as renewables. Using this nonnoble metal composite, hydrogenation of terminal C==C double bonds occurs under very mild and benign conditions (water or methanol, 40° to 60°C). The utility of Co@Chitosan-700 is showcased for efficient hydrogenation of the industrially relevant examples diisobutene, fatty acids, and their triglycerides. Because of the magnetic behavior of this material and water as solvent, product separation and recycling of the catalyst are straightforward.

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43

Landge, Vinod G., Vinita Yadav, Murugan Subaramanian, Pragya Dangarh, and Ekambaram Balaraman. "Nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones with the liberation of H2." Chemical Communications 55, no. 43 (2019): 6130–33. http://dx.doi.org/10.1039/c9cc02603g.

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A nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones to access various terminal and internal olefins with the liberation of hydrogen gas is reported. The present protocol has been used for E-selective synthesis of DMU-212, and Resveratrol.

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44

Liu, Bin, An Jie Wang, and Chen Guang Liu. "Reactivity of Olefins and Thiophenes in Hydrodesulfurization of FCC Gasoline." Advanced Materials Research 881-883 (January 2014): 271–78. http://dx.doi.org/10.4028/www.scientific.net/amr.881-883.271.

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The reactivity of olefins and S-compounds and their distributions in different catalyst-bed lengths were experimentally evaluated with a FCC gasoline in a high-pressure fixed-bed continuous flow pilot unit over the CoMoS/γ-Al2O3 catalyst. The evaluation results demonstrated that the increased steric hindrances around the double bond (C=C) and that to the thiophene molecules could suppress the hydrogenation of olefins and hydrodesulfurization (HDS) of S-compounds, respectively. Meanwhile, the reaction temperatures could influence the acidic property of the CoMoS active phase confirmed by FT-IR analysis, and thus induced the different reactions. It was found that the isomerization of terminal olefins to internal olefins was promoted by the Brønsted acid sites (-SH) at low temperatures, as well as the skeletal isomerization by the strong Lewis acid sites occurred to a minor extent at high temperatures. Besides, the distributions of olefins and S-compounds in different catalyst-bed lengths showed that the removal of S-compounds reached 80% of its maximum conversion at the first 40% of the reactor length, however, the saturation of olefins increased linearly as the reactor length increased. Therefore, a new catalyst-loading method was developed, i.e., the upper 40% of the reactor length filling with catalyst of high HDS activity and the bottom 60% with catalyst of low olefin saturation activity, respectively. The evaluation results showed that the graded catalyst loading process showed higher selectivity in HDS of FCC gasoline.

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45

Vicera, Clara, Raphael Dada, and Rylan J. Lundgren. "Z-Selective Hydrofunctionalization of Dienes." Alberta Academic Review 2, no. 2 (September 23, 2019): 77–78. http://dx.doi.org/10.29173/aar74.

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Olefins play a fundamental role in synthetic organic chemistry because they are useful building blocks that create molecules. However, geometry control (E- vs Z-) in olefin synthesis is of utmost importance because the olefin geometry has a tremendous impact on its physical, chemical and biological properties. Additionally, Z-olefins are less stable compared to their E-olefin counterparts; due to this difference, general methods to make olefins results in more cases of E-olefins production with relatively fewer Z-olefins caused by its instability. It has been reported that Z-olefins can be synthesized from dienes through a rhodium-catalyzed formate mediated transformation, with tolerance to several reducible functional groups. With this successful method in hand, the focus is to make functionalized Z-alkenes while still maintaining tolerance to reducible functional groups under mild reaction conditions. Thus, this project presents the production of Z-olefins through rhodium-catalyzed hydrofunctionalization using the starting materials, dienes and aldehydes. This method requires an inert atmosphere and the reaction progress can be monitored by Nuclear Magnetic Resonance (NMR) using an internal standard to quantify the amount of product formed. In this process, it was observed that the starting material was consumed until more than 95% conversion. In addition, the possibility of using different dienes, such as diene esters and phenyl dienes, as well as different aldehydes could further broaden the scope of this method. The usefulness of this process can be applied to the production of complex molecules. For example, in the synthesis of a glucagon receptor antagonist, which is a drug that is used in the treatment of diabetes. Currently, there is a limited number of methods used to create Z-olefins; however, this proven procedure can be further applied in other hydrofunctionalization

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46

Bagh, Bidraha, and Douglas W. Stephan. "Half sandwich ruthenium(ii) hydrides: hydrogenation of terminal, internal, cyclic and functionalized olefins." Dalton Trans. 43, no. 41 (2014): 15638–45. http://dx.doi.org/10.1039/c4dt02407a.

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Ruthenium(ii) complexes 2b–e with the general formula RuCl₂(p-cymene)(NHC) were reacted with Et₃SiH to generate a series of ruthenium(ii) hydrides 5b–e. These compounds 5b–e are effective catalysts for the hydrogenation of terminal, internal and cyclic and functionalized olefins.

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47

Song, Chuanling, Yihua Sun, Jianwu Wang, Hui Chen, Jiannian Yao, Chen-Ho Tung, and Zhenghu Xu. "Successive Cu/Pd transmetalation relay catalysis in stereoselective synthesis of tetraarylethenes." Organic Chemistry Frontiers 2, no. 10 (2015): 1366–73. http://dx.doi.org/10.1039/c5qo00205b.

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A new and efficient strategy for the synthesis of tetraaryl-substituted olefins with two cis furans based on a Cu/Pd catalyzed oxidative coupling reaction of cyclopropene with internal alkyne was developed. These novel tetraarylethenes were fully characterized and proved to be good AIE luminogens.

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48

Jia, Xiaofei, Zheng Wang, Chungu Xia, and Kuiling Ding. "Novel spiroketal-based diphosphite ligands for hydroformylation of terminal and internal olefins." Catalysis Science & Technology 3, no. 8 (2013): 1901. http://dx.doi.org/10.1039/c3cy00187c.

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49

Lu, Xiao-Yu, Jing-Song Li, Mei-Lan Hong, Jin-Yu Wang, and Wen-Jing Ma. "Synthesis of trisubstituted olefins via nickel-catalyzed decarboxylative hydroalkylation of internal alkynes." Tetrahedron 74, no. 49 (December 2018): 6979–84. http://dx.doi.org/10.1016/j.tet.2018.10.037.

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50

Alper, Howard, Krzysztof Januszkiewicz, and David J. H. Smith. "Palladium chloride and polyethylene glycol promoted oxidation of terminal and internal olefins." Tetrahedron Letters 26, no. 19 (January 1985): 2263–64. http://dx.doi.org/10.1016/s0040-4039(00)95069-x.

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Journal articles on the topic 'Difunctionnalization of internal olefins'

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