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Journal articles on the topic 'Difunctionnalization of internal olefins'

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Published: 24 May 2025

Last updated: 30 July 2025

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1

Seayad, A. "Internal Olefins to Linear Amines." Science 297, no. 5587 (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 (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

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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6

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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7

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

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8

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 (2015): 2488–91. http://dx.doi.org/10.1016/j.tetlet.2015.03.096.

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9

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

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10

Wen, Jiangwei, Longfei Zhang, Xiaoting Yang, et al. "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 H<sub>2</sub>O-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 та ін. "Synthesis of internal olefins by direct coupling of alcohols and olefins over Moβ zeolite". Catalysis Communications 123 (квітень 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 (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 (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 (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 (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 (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

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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 (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, et al. "Copper-Catalyzed Enantioselective Cyclopropanation of Internal Olefins with Diazomalonates." Organic Letters 19, no. 21 (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 (2015): no. http://dx.doi.org/10.1002/chin.201534227.

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21

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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22

de Klerk, Arno, Siphamandla W. Hadebe, Jude R. Govender та ін. "Linear α-Olefins from Linear Internal Olefins by a Boron-Based Continuous Double-Bond Isomerization Process". Industrial & Engineering Chemistry Research 46, № 2 (2007): 400–410. http://dx.doi.org/10.1021/ie060476c.

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23

Chen, Caiyou, Pan Li, Zhoumi Hu, et al. "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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24

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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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

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

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28

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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29

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 (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 enan

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30

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 (2020): 480–91. http://dx.doi.org/10.1002/ajoc.201900741.

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31

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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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)<sub>2</sub>H], promoted by zirconocene dichloride [Cp<sub>2</sub>ZrCl<sub>2</sub>] has been studied.

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33

Song, Lijuan, Qiang Feng, Yong Wang, et al. "Ru-Catalyzed Migratory Geminal Semihydrogenation of Internal Alkynes to Terminal Olefins." Journal of the American Chemical Society 141, no. 43 (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 (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 (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 (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 (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 (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 (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 (2013): 2944–48. http://dx.doi.org/10.1002/anie.201209541.

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41

Scharnagl, Florian Korbinian, Maximilian Franz Hertrich, Francesco Ferretti, et al. "Hydrogenation of terminal and internal olefins using a biowaste-derived heterogeneous cobalt catalyst." Science Advances 4, no. 9 (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, h

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42

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 (2002): 9038–39. http://dx.doi.org/10.1021/ja0263386.

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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

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45

Vicera, Clara, Raphael Dada, and Rylan J. Lundgren. "Z-Selective Hydrofunctionalization of Dienes." Alberta Academic Review 2, no. 2 (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 syn

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46

Song, Chuanling, Yihua Sun, Jianwu Wang, et al. "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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47

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 RuCl<sub>2</sub>(p-cymene)(NHC) were reacted with Et<sub>3</sub>SiH 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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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 (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 (1985): 2263–64. http://dx.doi.org/10.1016/s0040-4039(00)95069-x.

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