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Journal articles on the topic 'C₂-C₃ alkenes'

Author: Grafiati

Published: 7 June 2025

Last updated: 2 August 2025

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1

Bower, John F., Timothy P. Aldhous, Raymond W. M. Chung, and Andrew G. Dalling. "Enantioselective Intermolecular Murai-Type Alkene Hydroarylation Reactions." Synthesis 53, no. 17 (2021): 2961–75. http://dx.doi.org/10.1055/s-0040-1720406.

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AbstractStrategies that enable the efficient assembly of complex building blocks from feedstock chemicals are of paramount importance to synthetic chemistry. Building upon the pioneering work of Murai and co-workers in 1993, C–H-activation-based enantioselective hydroarylations of alkenes offer a particularly promising framework for the step- and atom-economical installation of benzylic stereocenters. This short review presents recent intermolecular enantioselective Murai-type alkene hydroarylation methodologies and the mechanisms by which they proceed.1 Introduction2 Enantioselective Hydroary

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2

Grossi, Vincent, Cristiana Cravo-Laureau, Alain Méou, Danielle Raphel, Frédéric Garzino, and Agnès Hirschler-Réa. "Anaerobic 1-Alkene Metabolism by the Alkane- and Alkene-Degrading Sulfate Reducer Desulfatibacillum aliphaticivorans Strain CV2803T." Applied and Environmental Microbiology 73, no. 24 (2007): 7882–90. http://dx.doi.org/10.1128/aem.01097-07.

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ABSTRACT The alkane- and alkene-degrading, marine sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803T, known to oxidize n-alkanes anaerobically by fumarate addition at C-2, was investigated for its 1-alkene metabolism. The total cellular fatty acids of this strain were predominantly C-(even number) (C-even) when it was grown on C-even 1-alkenes and predominantly C-(odd number) (C-odd) when it was grown on C-odd 1-alkenes. Detailed analyses of those fatty acids by gas chromatography-mass spectrometry after 6- to 10-week incubations allowed the identification of saturate

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3

Maraswami, Manikantha, and Teck-Peng Loh. "Transition-Metal-Catalyzed Alkenyl sp2 C–H Activation: A Short Account." Synthesis 51, no. 05 (2019): 1049–62. http://dx.doi.org/10.1055/s-0037-1611649.

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Alkenes are ubiquitous in Nature and their functionalization continues to attract attention from the scientific community. On the other hand, activation of alkenyl sp2 C–H bonds is challenging due to their chemical properties. In this short account, we elucidate, discuss and describe the utilization of transition-metal catalysts in alkene activation and provide useful strategies to synthesize organic building blocks in an efficient and sustainable manner.1 Introduction2 Breakthrough3 Controlling E/Z, Z/E Selectivity3.1 Esters and Amides as Directing Groups3.2 The Chelation versus Non-Chelation

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4

Tomita, Ren, Yusuke Yasu, Takashi Koike, and Munetaka Akita. "Direct C–H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis." Beilstein Journal of Organic Chemistry 10 (May 12, 2014): 1099–106. http://dx.doi.org/10.3762/bjoc.10.108.

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Background: Trifluoromethylated alkene scaffolds are known as useful structural motifs in pharmaceuticals and agrochemicals as well as functional organic materials. But reported synthetic methods usually require multiple synthetic steps and/or exhibit limitation with respect to access to tri- and tetrasubstituted CF3-alkenes. Thus development of new methodologies for facile construction of Calkenyl–CF3 bonds is highly demanded. Results: The photoredox reaction of alkenes with 5-(trifluoromethyl)dibenzo[b,d]thiophenium tetrafluoroborate, Umemoto’s reagent, as a CF3 source in the presence of [Ru

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5

Wrackmeyer, Bernd, Khadija Shahid, and Saqib Ali. "1,1-Ethylboration of Alkyn-1-yl- (dichloro)silanes: Alkenes Bearing Dichlorosilyl and Diethylboryl Groups." Zeitschrift für Naturforschung B 60, no. 5 (2005): 590–92. http://dx.doi.org/10.1515/znb-2005-0520.

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The 1,1-ethylboration of dichloro(hexyn-1-yl)silane, Cl2 Si(H)-C≡C-Bu, affords selectively an alkene which is the first example with dialkylboryl and dichlorosilyl groups in cis-positions at the C=C bond. The analogous reaction of dichloro( trimethylsilylethynyl)silane, Cl2(H)Si-C≡C-Si Me3, leads to a 4:1 mixture of alkenes, in one of which the boryl and dichlorosilyl groups are in trans-positions. The alkenes were characterized by a consistent set of NMR data.

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6

Gu, Zheng-Yang, Yang Wu, Xiaoguang Bao, Ji-Bao Xia, and Feng Jin. "Intermolecular C–H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis." Synthesis 53, no. 18 (2021): 3361–71. http://dx.doi.org/10.1055/a-1401-4486.

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AbstractAn atom- and step-economic intermolecular multi-component palladium-catalyzed C–H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho-directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

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7

Chae, Eunji, and Sung-Seen Choi. "Influence of Molecular Weight and Temperature on the Pyrolysis Behavior of Polyethylene." Polymers 17, no. 5 (2025): 576. https://doi.org/10.3390/polym17050576.

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The pyrolysis technique is a useful recycling method for waste polyethylene (PE). Various PEs with different molecular weights have been produced and are widely used. The major pyrolysis products of PE include alkadienes (CnH2n−2), alkenes (CnH2n), and alkanes (CnH2n+2). In this study, the differences in pyrolysis behavior of PE based on its molecular weight and the pyrolysis temperature (423–764 °C) were investigated using four types of PEs, with Mw = 2.0 ´ 103, 16.0 ´ 103, 28.3 ´ 103, and 56.8 ´ 103 g/mol. More specifically, the pyrolysis products were compared in terms of their type (alkane

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8

Sun, Kai, Fengji Ma, Lulu Liu, et al. "Iodine-mediated regioselective C–N and C–I bond formation of alkenes." RSC Advances 5, no. 100 (2015): 82492–95. http://dx.doi.org/10.1039/c5ra14407h.

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Iodine mediated intermolecular C–N and C–I bonds formation of alkenes was realized. A series of alkenes could be converted into the aminoiodination products, which are versatile building blocks in organic synthesis and medicinal chemistry.

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9

Martin, Alonso David, Jesse Bond, Ruiz Juan Carlos Serrano, and James Dumesic. "Production of liquid hydrocarbon transportation fuels by oligomerization of biomass-derived C9 alkenes." Green Chem 12 (April 26, 2010): 992–99. https://doi.org/10.1039/C001899F.

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A process is described to produce renewable liquid fuels, similar to existing petroleum-derived transportation fuels, through the oligomerization over solid acid catalysts of C<sub>9</sub>-alkenes derived from γ-valerolactone (GVL). Larger, non-terminal alkenes are shown to be less reactive than short chain α-alkenes for oligomerization over solid acid sites, and Amberlyst-70 has been identified to be an active and stable catalyst with sufficient acidity to couple C<sub>9</sub>-alkenes. The inhibiting effect of water on alkene&

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10

Zhang, Ping, Peng Huo, Xuan Zhang, Qin-Yu Zhu, and Jie Dai. "C–C to CC conversion within a supramolecular framework of tetrathiafulvalene: a confinement effect and an oxygen related dehydrogenation." Chemical Communications 54, no. 53 (2018): 7334–37. http://dx.doi.org/10.1039/c8cc03197e.

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A supramolecular framework with a TTF derivative can activate strong C–H bonds and transform alkanes to alkenes at room temperature under the confinement effect of the framework in the presence of oxygen.

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11

Cavanagh, Craig W., Miles H. Aukland, Alan Hennessy, and David J. Procter. "Iron-mediated C–H coupling of arenes and unactivated terminal alkenes directed by sulfur." Chemical Communications 51, no. 45 (2015): 9272–75. http://dx.doi.org/10.1039/c5cc02676h.

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12

Soloshonok, Vadim A., and Donna J. Nelson. "Alkene selenenylation: A comprehensive analysis of relative reactivities, stereochemistry and asymmetric induction, and their comparisons with sulfenylation." Beilstein Journal of Organic Chemistry 7 (June 3, 2011): 744–58. http://dx.doi.org/10.3762/bjoc.7.85.

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A broad perspective of various factors influencing alkene selenenylation has been developed by concurrent detailed analysis of key experimental and theoretical data, such as asymmetric induction, stereochemistry, relative reactivities, and comparison with that of alkene sulfenylation. Alkyl group branching α to the double bond was shown to have the greatest effect on alkene reactivity and the stereochemical outcome of corresponding addition reactions. This is in sharp contrast with other additions to alkenes, which depend more on the degree of substitution on C=C or upon substituent electronic

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13

Yang, Xu-Heng, Wen-Ting Wei, Hai-Bing Li, Ren-Jie Song, and Jin-Heng Li. "Oxidative coupling of alkenes with amides using peroxides: selective amide C(sp3)–H versus C(sp2)–H functionalization." Chem. Commun. 50, no. 85 (2014): 12867–69. http://dx.doi.org/10.1039/c4cc05051g.

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14

Bakewell, Clare, Andrew J. P. White, and Mark R. Crimmin. "Reversible alkene binding and allylic C–H activation with an aluminium(i) complex." Chemical Science 10, no. 8 (2019): 2452–58. http://dx.doi.org/10.1039/c8sc04865g.

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The monomeric molecular aluminium(i) complex 1 [{(ArNCMe)<sub>2</sub>CH}Al] (Ar = 2,6-di-iso-propylphenyl) reacts with a series of terminal and strained alkenes including ethylene, propylene, allylbenzene and norbornene to form alkene bound products.

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15

Kakiuchi, Fumitoshi, Naoki Kimura, Shiori Katta, Yoichi Kitazawa, and Takuya Kochi. "Deuterium-Labeling Studies on the C–H/Olefin Coupling of Aromatic Ketones Catalyzed by Fe(PMe3)4." Synthesis 53, no. 18 (2021): 3383–89. http://dx.doi.org/10.1055/s-0040-1706040.

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AbstractDeuterium-labeling experiments were performed for the Fe(PMe3)4-catalyzed C–H/olefin coupling using a deuterium-labeled aromatic ketone with various alkenes. While the reactions with a variety of alkenes provided the linear alkylation products formed via 1,2-insertion of alkene into an Fe–H bond, the reversible 2,1-insertion proceeded during the reaction highly depends on the choice of the alkene. No H/D scrambling resulting from 2,1-insertion/β-elimination was detected for the reactions with a vinylsilane and N-vinylcarbazole, but the reactions with styrenes are considered to involve

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16

Qin, Qixue, Weijing Wang, Cheng Zhang, Song Song, and Ning Jiao. "A metal-free desulfurizing radical reductive C–C coupling of thiols and alkenes." Chemical Communications 55, no. 71 (2019): 10583–86. http://dx.doi.org/10.1039/c9cc05378f.

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17

Megawati, Eka, Hakim Bangun, Imam Putra, et al. "Phytochemical Analysis by FTIR of Zanthoxylum Acanthopodium, DC Fruit Ethanol Extract, N-hexan, Ethyl Acetate and Water Fraction." Medical Archives 77, no. 3 (2023): 183. http://dx.doi.org/10.5455/medarh.2023.77.183-188.

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Background:Andaliman fruit is used as spice in Batak cuisine, North Sumatera, Indonesia. The potency of andaliman fruit extract as herbal medicine is widely studied. Many studies elaborate the benefits of andaliman fruit extract as an antioxidant, antibacterial or anticancer. Objective: The aim of this study was to identify the phytochemical compounds of andaliman fruit extract and its fractions. Methods: The andaliman fruit was originated from Balige city, Tobasa Regency, North Sumatera. The extract was made by maceration within ethanol and followed by fractionation with n-hexan, ethyl acetat

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18

White, Derick R., Evan C. Bornowski, and John P. Wolfe. "Pd‐Catalyzed C−C, C−N, and C−O Bond‐Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates." Israel Journal of Chemistry 60, no. 3-4 (2020): 259–67. http://dx.doi.org/10.1002/ijch.201900108.

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19

Xiong, Tao, Qian Zhang, and Qian Zhang. "Transition-Metal-Catalyzed Alkylation of Polyfluoroarenes through C–F Bond Cleavage." Synlett 32, no. 14 (2021): 1379–84. http://dx.doi.org/10.1055/a-1479-8264.

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AbstractThe polyfluoroarenes are a subgroup of organofluorines that are widely utilized in both medicinal chemistry and materials science. We briefly summarize recent advances in the synthesis of these important compounds, with particular attention to our recent CuH-catalyzed defluorinative alkylation of polyfluoroarenes with alkenes in a highly site-selective C–F bond-cleavage fashion.1 Introduction2 Transition-Metal-Catalyzed Alkylation through Selective C–F Bond Cleavage3 CuH-Catalyzed Defluorinative Alkylation of Polyfluoroarenes with Alkenes4 Summary and Outlook

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20

Song, Ren-Jie, Jin-Heng Li, Gao-Hui Pan, Ye-Xiang Xie та Shenglian Luo. "Synthesis of γ-Amino Esters by Copper-Catalyzed Intermolecular 1,2-Aminoalkylation of Alkenes with Amines and α-Bromoalkyl Esters". Synthesis 50, № 08 (2018): 1651–60. http://dx.doi.org/10.1055/s-0036-1591903.

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A new copper-catalyzed intermolecular 1,2-aminoalkylation of alkenes with α-bromoalkyl esters and amines for the synthesis of γ-amino esters is described. Employing the Cu(OTf)2 and 2,2′-bipyridine catalytic system, the three-component reaction allows the formation of two new chemical bonds, including one C–C bond and one C–N bond, in a single reaction, and represents a new alkene difunctionalization using a radical strategy.

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21

Sharma, Satyasheel, Sangil Han, Mirim Kim, et al. "Rh-catalyzed oxidative C–C bond formation and C–N bond cleavage: direct access to C2-olefinated free (NH)-indoles and pyrroles." Org. Biomol. Chem. 12, no. 11 (2014): 1703–6. http://dx.doi.org/10.1039/c3ob42605j.

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22

Yan, Jie, Junxing Wang, and Weijian Sheng. "Iodine-Mediated Vicinal Difunctionalization of Alkenes: A Convenient Method for Building C–Se and C–S Bonds." Synlett 29, no. 12 (2018): 1654–58. http://dx.doi.org/10.1055/s-0037-1610145.

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A novel I2-mediated procedure is developed for building C–Se and C–S bonds simultaneously from alkenes, diselenides and sodium dithiocarbamates. This difunctionalization of alkenes is carried out in the presence of I2 and air, and exhibits good characteristics such as being transition-metal-free, requiring mild reaction conditions and simple procedures. The approach provides the product β-selanylethyl dithiocarbamates with high regioselectivity and in good yields. A plausible electrophilic addition mechanism is hypothesized.

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23

Li, Shuai-Shuai, Cheng-Qi Wang, Hui Lin, Xiao-Mei Zhang, and Lin Dong. "Rhodium(iii)-catalyzed C–C coupling of 7-azaindoles with vinyl acetates and allyl acetates." Organic & Biomolecular Chemistry 14, no. 1 (2016): 229–37. http://dx.doi.org/10.1039/c5ob02096d.

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24

Beller, Harry R., Ee-Been Goh, and Jay D. Keasling. "Genes Involved in Long-Chain Alkene Biosynthesis in Micrococcus luteus." Applied and Environmental Microbiology 76, no. 4 (2009): 1212–23. http://dx.doi.org/10.1128/aem.02312-09.

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ABSTRACT Aliphatic hydrocarbons are highly appealing targets for advanced cellulosic biofuels, as they are already predominant components of petroleum-based gasoline and diesel fuels. We have studied alkene biosynthesis in Micrococcus luteus ATCC 4698, a close relative of Sarcina lutea (now Kocuria rhizophila), which 4 decades ago was reported to biosynthesize iso- and anteiso-branched, long-chain alkenes. The underlying biochemistry and genetics of alkene biosynthesis were not elucidated in those studies. We show here that heterologous expression of a three-gene cluster from M. luteus (Mlut_1

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25

Trifonov, A. A., I. V. Basalov, and A. A. Kissel. "Use of organolanthanides in the catalytic intermolecular hydrophosphination and hydroamination of multiple C–C bonds." Dalton Transactions 45, no. 48 (2016): 19172–93. http://dx.doi.org/10.1039/c6dt03913h.

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26

Lah, Hafiz Ul, Faheem Rasool, and Syed Khalid Yousuf. "Palladium catalyzed C(sp2)–C(sp2) bond formation. A highly regio- and chemoselective oxidative Heck C-3 alkenylation of pyrones and pyridones." RSC Advances 5, no. 96 (2015): 78958–61. http://dx.doi.org/10.1039/c5ra12631b.

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Palladium catalysed ligand free highly regio- and chemoselective dehydrogenative C-3 alkenylation of pyrones and unprotected pyridones from unactivated alkenes is reported. Simple reaction conditions and broad substrate scope make the process useful.

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27

Aboonajmi, Jasem, Farhad Panahi, Mina Aali Hosseini, Mahdi Aberi, and Hashem Sharghi. "Iodine-catalyzed synthesis of benzoxazoles using catechols, ammonium acetate, and alkenes/alkynes/ketones via C–C and C–O bond cleavage." RSC Advances 12, no. 32 (2022): 20968–72. http://dx.doi.org/10.1039/d2ra03340b.

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A metal-free one-pot multi-component method for the efficient synthesis of 2-aryl benzoxazoles via coupling of catechols, ammonium acetate and alkenes/alkynes/ketones using an I2–DMSO catalyst system is illustrated.

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28

Lim, Yeong-Gweon, Jung-Bu Kang, and Yong Hae Kim. "Rhodium catalysed cross-coupling of alkenes by C–H activation: addition of alkenic C–H bonds of 2-vinylpyridines to alkenes." Chem. Commun., no. 5 (1996): 585–86. http://dx.doi.org/10.1039/cc9960000585.

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29

Nájera, Carmen, and José M Sansano. "Asymmetric Intramolecular Carbocyanation of Alkenes by CC Bond Activation." Angewandte Chemie International Edition 48, no. 14 (2009): 2452–56. http://dx.doi.org/10.1002/anie.200805601.

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30

Wang, Hui, Rui Jia, Mei Hong, Hongyan Miao, Bangqing Ni, and Tengfei Niu. "Hydroxyl radical-mediated oxidative cleavage of CC bonds and further esterification reaction by heterogeneous semiconductor photocatalysis." Green Chemistry 23, no. 17 (2021): 6591–97. http://dx.doi.org/10.1039/d1gc01931g.

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31

Iqbal, S. A., J. Pahl, K. Yuan, and M. J. Ingleson. "Intramolecular (directed) electrophilic C–H borylation." Chemical Society Reviews 49, no. 13 (2020): 4564–91. http://dx.doi.org/10.1039/c9cs00763f.

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32

Trofimov, Boris, Nina Gusarova, and Nataliya Chernysheva. "Catalyst- and Solvent-Free Addition of the P–H Species to Alkenes and Alkynes: A Green Methodology for C–P Bond Formation." Synthesis 49, no. 21 (2017): 4783–807. http://dx.doi.org/10.1055/s-0036-1588542.

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Traditional methods for C–P bond formation via direct addition of P–H species to unsaturated compounds are usually implemented in the presence of base and metal catalysts or radical initiators in various organic solvents. During the last five years, a novel efficient and general catalyst/initiator- and solvent-free version of the hydrophosphination and hydrophosphinylation of multiple C–C bonds with H-phosphines and their chalcogenides has begun to develop and it is attracting growing attention. This approach corresponds to the recently emerged pot-, atom-, and step-economy (PASE) green paradi

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33

Chen, Hao, Jianmin Wang, Xuechuan Hong, Hai-Bing Zhou, and Chune Dong. "A simple and straightforward approach toward selective C=C bond reduction by hydrazine." Canadian Journal of Chemistry 90, no. 9 (2012): 758–61. http://dx.doi.org/10.1139/v2012-057.

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A simple and straightforward method for reducing the C=C double bond with hydrazine is described. A number of representative C=C bonds in various steric and electronic environments were examined. Substituted alkenes can be selectively reduced in EtOH in the presence of hydrazine to give the corresponding products in up to 100% yields.

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34

Xiong, Baojian, Xiaoqin Zeng, Shasha Geng, Shuo Chen, Yun He, and Zhang Feng. "Thiyl radical promoted chemo- and regioselective oxidation of CC bonds using molecular oxygen via iron catalysis." Green Chemistry 20, no. 19 (2018): 4521–27. http://dx.doi.org/10.1039/c8gc02369g.

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35

Ding, Ya, Hao Li, Yunge Meng, et al. "Direct synthesis of hydrazones by visible light mediated aerobic oxidative cleavage of the CC bond." Organic Chemistry Frontiers 4, no. 8 (2017): 1611–14. http://dx.doi.org/10.1039/c7qo00276a.

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A metal-free protocol through visible light mediated oxidative cleavage of CC bonds to directly construct CN bonds has been developed for the conversion of alkenes to hydrazones under mild conditions.

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36

Breton, Gary W., та Jazmine V. Ridlehoover. "Spontaneous Formation of Strained Anti-Bredt Bridgehead Alkenes upon Computational GeometryOptimization of Bicyclic β-Halo Carbanions". Organics 5, № 3 (2024): 205–18. http://dx.doi.org/10.3390/org5030010.

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Bridgehead alkenes are polycyclic molecules bearing at least one C=C bond that includes a bridgehead carbon atom. For small bicyclic systems, these bonds are highly strained due to geometric constraints placed on the sp2 hybridized carbon atoms. These small, strained molecules have been termed “anti-Bredt” alkenes. β-halo carbanions have served as convenient precursors to bridgehead alkenes in experimental studies. We observed that upon attempted computational geometric optimizations (ωB97X-D/aug-cc-pVDZ) of the precursors, spontaneous elimination of the halide occurs along with formation of t

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37

Jun, Chul-Ho, and Chang-Hee Lee. "Chelation-Assisted C–H and C–C Bond Activation of Allylic Alcohols by a Rh(I) Catalyst under Microwave Irradiation." Synlett 29, no. 06 (2017): 736–41. http://dx.doi.org/10.1055/s-0036-1591697.

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Chelation-assisted Rh(I)-catalyzed ketone synthesis from allylic alcohols and alkenes through C–H and C–C bond activations under microwave irradiation was developed. Aldimine is formed via olefin isomerization of allyl alcohol under Rh(I) catalysis and condensation with 2-amino-3-picoline, followed by continuous C–H and C–C bond activations to produce a dialkyl ketone. The addition of piperidine accelerates the reaction rate by promoting aldimine formation under microwave conditions.

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38

Ghosh, Ivy, Biswarup Chakraborty, Abhijit Bera, Satadal Paul, and Tapan Kanti Paine. "Selective oxygenation of C–H and CC bonds with H₂O₂ by high-spin cobalt(ii)-carboxylate complexes." Dalton Transactions 51, no. 6 (2022): 2480–92. http://dx.doi.org/10.1039/d1dt02235k.

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Cobalt(ii)–carboxylate complexes of the 6-Me3-TPA ligand in combination with hydrogen peroxide perform the oxygenation of aliphatic C–H bonds of alkanes and epoxidation of alkenes with high chemo- and stereo-selectivity. A metal-based oxidant is proposed as the active oxidant.

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39

Liu, Dapeng, and Aamir Farooq. "Thermal decomposition of alkenes: role of allylic C-C bond cleavage." Combustion and Flame 268 (October 2024): 113618. http://dx.doi.org/10.1016/j.combustflame.2024.113618.

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40

Schomaker, Jennifer, and Amirah Mat Lani. "Site-Selective, Catalyst-Controlled Alkene Aziridination." Synthesis 50, no. 22 (2018): 4462–70. http://dx.doi.org/10.1055/s-0037-1609858.

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Transition-metal-catalyzed nitrene transfer is a convenient method to introduce nitrogen into simple substrates through either alkene aziridination or C–H bond amination. Silver complexes have an unusual capability to accommodate a broad range of N-donor ligands and coordination geometries in catalysts competent for nitrene transfer. This behavior has resulted in the ability to achieve tunable chemoselectivity between aziridination and C–H bond amidation, as well as tunable site-selective functionalization between two different C–H bonds. In this paper, efforts to engage the diversity of silve

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41

Lu, Xi, Yini Wang, Kailin Xie, and Jian Zhang. "Cross-coupling reactions between alkenes by C−H cyclometallation." Synlett, April 4, 2023. http://dx.doi.org/10.1055/a-2068-6215.

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Alkenes are one of the most abundant raw feedstocks to construct complex chemicals, cross-coupling reactions using alkenes provides powerful methods toward valuable chemicals. In the past decade, cross-coupling reaction of simple alkenes by chelation-assisted alkenyl C−H functionalization has attracted many attentions due to its atom- and step efficiency, as well as excellent Z/E selectivity, proceeding by C−H exo-cyclometallation and endo-cyclometallation. In this Account, we would like to summarize transition-metal-catalyzed cross-coupling reactions between alkenes to generate 1,3-dienes by

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Meng, Qing-Yuan, and Pan-Feng Yuan. "Carboxylation of Alkenes with CO2 via Photocatalytic Cleavage of C=C Double Bonds." Synlett, May 14, 2024. http://dx.doi.org/10.1055/s-0043-1763755.

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AbstractThe cleavage of double bonds in alkenes constitutes an integral process in converting feedstock materials into high-value synthetic intermediates. Well-known examples such as the oxidative cleavage of olefins and olefin metathesis only facilitate the synthesis of oxygen-containing compounds and the recombination of olefins. Therefore, it is appealing to extend C=C double bond cleavage to yield more abundant transformations. Herein, we report a novel photocatalytic approach for the deconstructive carboxylation of alkenes with CO2 for the synthesis of carboxylic acids in the absence of t

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43

Mammadova, A., and A. Zeynalli. "CONVERSION OF METHANOL TO C₂-C₃ ALKENES ON MODIFIED HIGH-SILICA ZSM-5-TYPE ZEOLITES." Norwegian Journal of development of the International Science 155 (April 26, 2025). https://doi.org/10.5281/zenodo.15298371.

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<strong>Abstract</strong> To increase the selectivity for C₂-C₃ alkenes, catalysts based on ZSM-5 zeolite, modified with zinc, cobalt, gadolinium, and zirconium, were obtained using the impregnation method. The conversion of methanol to hydrocarbons was carried out in a flow reactor with a fixed catalyst bed in the temperature range of 300-350°C, under atmospheric pressure, in a nitrogen flow. It has been shown that H-ZSM-5 has low selectivity for C₂-C₃ alkenes (24.0%). The modified H-ZSM-5 with zinc, gadolinium, and zirconium improves selectivity for C₂-C₃ alkenes (52.6% - 63.6%) and redu

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44

Lee, Changseok, Huiyeong Seo, Jinwon Jeon та Sungwoo Hong. "γ-Selective C(sp3)–H amination via controlled migratory hydroamination". Nature Communications 12, № 1 (2021). http://dx.doi.org/10.1038/s41467-021-25696-z.

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AbstractRemote functionalization of alkenes via chain walking has generally been limited to C(sp3)–H bonds α and β to polar-functional units, while γ-C(sp3)–H functionalization through controlled alkene transposition is a longstanding challenge. Herein, we describe NiH-catalyzed migratory formal hydroamination of alkenyl amides achieved via chelation-assisted control, whereby various amino groups are installed at the γ-position of aliphatic chains. By tuning olefin isomerization and migratory hydroamination through ligand and directing group optimization, γ-selective amination can be achieved

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Kakiuchi, Fumitoshi, and Takuya Kochi. "Catalytic C–C Bond Formation via Aromatic C–H Bond Cleavage Using Low-Valent Iron-Phosphine Complexes." Synlett, July 24, 2025. https://doi.org/10.1055/a-2630-1454.

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AbstractThis article presents our findings on catalytic ortho-selective C–C bond formations through the cleavage of C–H bonds in aromatic ketones using low-valent iron-phosphine complexes. We describe four types of catalytic transformations that convert C–H bonds into C–C bonds. Reactions involving terminal alkenes, such as vinyl and allylsilanes, aliphatic alkenes, styrenes, vinyl ethers, and enamines, yield the corresponding linear alkylation products. The coupling reaction using methylenecyclopropanes yields homoallylation products via alkene 1,2-insertion, followed by β-carbon elimination.

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46

Liu, Ming-Shang, Hai-Wu Du, Huan Meng, Ying Xie, and Wei Shu. "Unified metal-free intermolecular Heck-type sulfonylation, cyanation, amination, amidation of alkenes by thianthrenation." Nature Communications 15, no. 1 (2024). http://dx.doi.org/10.1038/s41467-024-44746-w.

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AbstractDirect and site-selective C-H functionalization of alkenes under environmentally benign conditions represents a useful and attractive yet challenging transformation to access value-added molecules. Herein, a unified protocol for a variety of intermolecular Heck-type functionalizations of Csp2-H bond of alkenes has been developed by thianthrenation. The reaction features metal-free and operationally simple conditions for exclusive cine-selective C-H functionalization of aliphatic and aryl alkenes to forge C-C, C-N, C-P, and C-S bonds at room temperature, providing a general protocol for

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47

Xue, Wenxuan, Yijie Jiang, Hongcheng Lu, Bo You, Xu Wang, and Conghui Tang. "Direct C‐C Double Bond Cleavage of Alkenes Enabled by Highly Dispersed Cobalt Catalyst and Hydroxylamine." Angewandte Chemie, November 15, 2023. http://dx.doi.org/10.1002/ange.202314364.

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The utilization of a single‐atom catalyst to break C‐C bonds merges the merits of homogeneous and heterogeneous catalysis and presents an intriguing pathway for obtaining high‐value‐added products. Herein, a mild, selective, and sustainable oxidative cleavage of alkene to form oxime ether or nitrile was achieved by using atomically dispersed cobalt catalyst and hydroxylamine. Diversified substrate patterns, including symmetrical and unsymmetrical alkenes, di‐ and tri‐substituted alkenes, and late‐stage functionalization of complex alkenes were demonstrated. The reaction was successfully scaled

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48

Xue, Wenxuan, Yijie Jiang, Hongcheng Lu, Bo You, Xu Wang, and Conghui Tang. "Direct C‐C Double Bond Cleavage of Alkenes Enabled by Highly Dispersed Cobalt Catalyst and Hydroxylamine." Angewandte Chemie International Edition, November 15, 2023. http://dx.doi.org/10.1002/anie.202314364.

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The utilization of a single‐atom catalyst to break C‐C bonds merges the merits of homogeneous and heterogeneous catalysis and presents an intriguing pathway for obtaining high‐value‐added products. Herein, a mild, selective, and sustainable oxidative cleavage of alkene to form oxime ether or nitrile was achieved by using atomically dispersed cobalt catalyst and hydroxylamine. Diversified substrate patterns, including symmetrical and unsymmetrical alkenes, di‐ and tri‐substituted alkenes, and late‐stage functionalization of complex alkenes were demonstrated. The reaction was successfully scaled

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49

Qin, Shengxiang, Yaqi Zhang, Long Jiang, Man-Kin Tse, Albert S. C. Chan, and Liqin Qiu. "Acid-Catalyzed Regioselective Remote Heteroarylation of Alkenes via C=C Bond Migration." Green Chemistry, 2024. http://dx.doi.org/10.1039/d4gc03356f.

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We report herein the acid-catalyzed regioselective remote heteroarylation and reductive alkylation of alkenes. Various alkenes, including mono-, di-, tri-substituted alkenes and cyclic alkenes are applicable to this reaction. This method...

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50

Zhou, Jun, Bingyao Jiang, Yamato Fujihira, Zhengyu Zhao, Takanori Imai, and Norio Shibata. "Catalyst-free carbosilylation of alkenes using silyl boronates and organic fluorides via selective C-F bond activation." Nature Communications 12, no. 1 (2021). http://dx.doi.org/10.1038/s41467-021-24031-w.

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AbstractA regioselective carbosilylation of alkenes has emerged as a powerful strategy to access molecules with functionalized silylated alkanes, by incorporating silyl and carbon groups across an alkene double bond. However, to the best of our knowledge, organic fluorides have never been used in this protocol. Here we disclose the catalyst-free carbosilylation of alkenes using silyl boronates and organic fluorides mediated by tBuOK. The main feature of this transformation is the selective activation of the C-F bond of an organic fluoride by the silyl boronate without undergoing potential side

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