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Journal articles on the topic 'Ring-strained alkenes'

Author: Grafiati

Published: 22 July 2024

Last updated: 31 July 2025

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1

Jeganmohan, Masilamani, and Pinki Sihag. "Recent Advances in Transition-Metal-Catalyzed C–H Functionalization Reactions Involving Aza/Oxabicyclic Alkenes." Synthesis 53, no. 18 (2021): 3249–62. http://dx.doi.org/10.1055/a-1528-1711.

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AbstractBicyclic alkenes, including oxa- and azabicyclic alkenes, readily undergo activation with facial selectivity in the presence of transition-metal complexes. This is due to the intrinsic angle strain on the carbon–carbon double bonds in such unsymmetrical bicyclic systems. During the past decades considerable progress has been made in the area of ring opening of bicyclic strained rings by employing the concept of C–H activation. This short review comprehensively compiles the various C–H bond activation assisted reactions of oxa- and azabicyclic alkenes, viz., ring-opening reactions, hydr

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2

Nishimura, T., T. Hayashi, E. Tsurumaki, T. Kawamoto, and X. X. Guo. "Enantioselective Desymmetrization via Ring Opening of Strained Alkenes." Synfacts 2008, no. 11 (2008): 1191. http://dx.doi.org/10.1055/s-0028-1083422.

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3

Sanzone, Jillian R., and K. A. Woerpel. "High Reactivity of Strained Seven-Membered-Ring trans -Alkenes." Angewandte Chemie International Edition 55, no. 2 (2015): 790–93. http://dx.doi.org/10.1002/anie.201510056.

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4

Sanzone, Jillian R., and K. A. Woerpel. "High Reactivity of Strained Seven-Membered-Ring trans -Alkenes." Angewandte Chemie 128, no. 2 (2015): 800–803. http://dx.doi.org/10.1002/ange.201510056.

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5

Feng, Qiang, Qian Wang, and Jieping Zhu. "Oxidative rearrangement of 1,1-disubstituted alkenes to ketones." Science 379, no. 6639 (2023): 1363–68. http://dx.doi.org/10.1126/science.adg3182.

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The Wacker process, which is widely used to convert monosubstituted alkenes into the corresponding methyl ketones, is thought to proceed through a Pd II /Pd 0 catalytic cycle involving a β-hydride elimination step. This mechanistic scenario is inapplicable to the synthesis of ketones from the 1,1-disubstituted alkenes. Current approaches based on semi -pinacol rearrangement of Pd II intermediates are limited to the ring expansion of highly strained methylene cyclobutane derivatives. Herein, we report a solution to this synthetic challenge by designing a Pd II /Pd IV catalytic cycle incorporati

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6

Shahid, Shereena, Muhammad Faisal, Aamer Saeed, et al. "A Review on the Scope of TFDO-Mediated Oxidation in Organic Synthesis-- Reactivity and Selectivity." Current Organic Synthesis 15, no. 8 (2018): 1091–108. http://dx.doi.org/10.2174/1570179415666180831104324.

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Dioxiranes are three-membered strained ring peroxides that are typical archetype examples of electrophilic entities. A dioxirane-based oxidant named 3-methyl(trifluoromethyl)dioxirane (TFDO) is a fluorinated analogue of the extremely valuable oxidant dimethyldioxirane (DMDO). Owing to the strained threemembered ring and presence of electron-withdrawing trifluoromethyl group, TFDO is several times more reactive than DMDO and acts as a significant chemical reagent. Moreover, TFDO exhibits high regio-, chemo- and stereo-selectivity even under unusual reaction conditions, i.e. at pH values close t

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7

Ma, Jiajia, Shuming Chen, Peter Bellotti, et al. "Facile access to fused 2D/3D rings via intermolecular cascade dearomative [2 + 2] cycloaddition/rearrangement reactions of quinolines with alkenes." Nature Catalysis 5, no. 5 (2022): 405–13. http://dx.doi.org/10.1038/s41929-022-00784-5.

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AbstractHybrid fused two-dimensional/three-dimensional (2D/3D) rings are important pharmacophores in drugs owing to their unique structural and physicochemical properties. Preparation of these strained ring systems often requires elaborate synthetic effort and exhibits low efficiency, thus representing a limiting factor in drug discovery. Here, we report two types of energy-transfer-mediated cascade dearomative [2 + 2] cycloaddition/rearrangement reactions of quinoline derivatives with alkenes, which provide a straightforward avenue to 2D/3D pyridine-fused 6−5−4−3- and 6−4−6-membered ring syst

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8

Sorensen, T. S., and F. Sun. "cis-2,3-Di-tert-butylcyclopropanones." Canadian Journal of Chemistry 75, no. 7 (1997): 1030–40. http://dx.doi.org/10.1139/v97-123.

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The preparation of the strained cis-2,3-di-tert-butylcyclopropanone 2 from the acyclic compound, α,α′-dibromodineopentyl ketone 1, using a previously reported methodology, is dramatic evidence of both the existence of oxyallyl intermediates in the mechanism of this reaction, and of the integrity with which oxyallyls ring-close to cyclopropanones by a disrotatory route. Because of the bulky cis substituents, cyclopropanone 2 exhibits a number of unusual spectroscopic features (as compared to the trans isomer 5). With the aid of ab initio calculations on 2 and 5, it can be shown that the C2—C3 b

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9

Boutin, Rebecca, Samuel Koh, and William Tam. "Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene." Current Organic Synthesis 16, no. 4 (2019): 460–84. http://dx.doi.org/10.2174/1570179416666181122094643.

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Background: Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate capable of undergoing multiple types of transformations due to three key structural features: a free alkene, a bridged oxygen atom, and a highly strained ring system. Most notably, ring-opening reactions of OBD using transition metal catalysts and nucleophiles produce multiple stereocenters in a single step. The resulting dihydronaphthalene framework is found in many natural products, which have been shown to be biologically active. Objective: This review will provide an overview of transition metal-catalyzed reactions

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10

Wanapun, D., K. A. Van Gorp, N. J. Mosey, M. A. Kerr, and T. K. Woo. "The mechanism of 1,3-dipolar cycloaddition reactions of cyclopropanes and nitrones A theoretical study." Canadian Journal of Chemistry 83, no. 10 (2005): 1752–67. http://dx.doi.org/10.1139/v05-182.

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The 1,3-dipolar cycloaddition reaction of cyclopropanes and nitrones to give tetrahydro-1,2-oxazine has been studied with density functional theory calculations at the B3LYP/6-31+G(d,p) level of theory. Realistic substituents were modelled including those at the 2-, 3-, 4-, and 6-positions of the final oxazine ring product. The strained σ bond of the cyclopropane was found to play the role of an alkene in a conventional [3+2] dipolar cycloaddition. Two distinct, but similar, reaction mechanisms were found an asymmetric concerted pathway and a stepwise zwitterionic pathway. The reaction barri

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11

Shi, Dingcheng, Xingxuan Xia, Binlin Zhao та Yu Yuan. "Diboron-Promoted Iron-Catalyzed Denitrative Vinylation of β-Nitrostyrenes with Cycloketoimes". Organic & Biomolecular Chemistry, 2023. http://dx.doi.org/10.1039/d3ob00890h.

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We have developed a new iron-catalyzed ring opening alkenylation of cycloketoximes with β-nitrostyrenes for the facile synthesis of flexible distal-cyanoalkyl alkenes. Both non-active strained cycloketoximes and less-strained cycloketoximes could be...

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12

Wang, Hui, Lihua Wei, Jiayu Huang, et al. "Divergent Asymmetric Synthesis of Bonnadiene and ent‐Polytrichastrene B." Angewandte Chemie, June 18, 2025. https://doi.org/10.1002/ange.202507961.

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We report herein the first asymmetric total synthesis of bonnadiene and ent‐polytrichastrene B, two diterpenoids that share a common spirotricyclic skeleton. Notably, ent‐polytrichastrene B also features a highly strained, sterically congested tetrasubstituted cyclopropane moiety, presenting significant synthetic challenges in both its construction and stereochemical control. The synthesis features: (1) Palladium‐catalyzed enantioselective redox‐relay Heck alkenylation between electron‐withdrawing alkenyl triflate and primary alkenol to form the stereocenter at C7; (2) diastereoselective intra

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13

Wang, Hui, Lihua Wei, Jiayu Huang, et al. "Divergent Asymmetric Synthesis of Bonnadiene and ent‐Polytrichastrene B." Angewandte Chemie International Edition, June 18, 2025. https://doi.org/10.1002/anie.202507961.

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We report herein the first asymmetric total synthesis of bonnadiene and ent‐polytrichastrene B, two diterpenoids that share a common spirotricyclic skeleton. Notably, ent‐polytrichastrene B also features a highly strained, sterically congested tetrasubstituted cyclopropane moiety, presenting significant synthetic challenges in both its construction and stereochemical control. The synthesis features: (1) Palladium‐catalyzed enantioselective redox‐relay Heck alkenylation between electron‐withdrawing alkenyl triflate and primary alkenol to form the stereocenter at C7; (2) diastereoselective intra

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14

Han, You-Feng, Ying Huang, Hao Liu, Zhong-Hua Gao, Chun-Lin Zhang, and Song Ye. "Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes." Nature Communications 13, no. 1 (2022). http://dx.doi.org/10.1038/s41467-022-33444-0.

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AbstractThree-component carboacylation of simple alkenes with readily available reagents is challenging. Transition metal-catalysed intermolecular carboacylation works for alkenes with strained ring or directing groups. Herein, we develop a photoredox cooperative N-heterocyclic carbene/Pd-catalysed alkylacylation of simple alkenes with aldehydes and unactivated alkyl halides to provide ketones in good yields. This multicomponent coupling reaction features a wide scope of alkenes, broad functional group compatibility and free of exogenous photosensitizer or external reductant. In addition, a se

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15

Chen, Shaowei, Meiyun Gao, Xiaoqian He, and Xiao Shen. "Photo-induced ring-maintaining hydrosilylation of unactivated alkenes with hydrosilacyclobutanes." Nature Communications 16, no. 1 (2025). https://doi.org/10.1038/s41467-025-57705-w.

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Abstract Increasing attention has been paid to silacyclobutanes because of their wide application in ring opening and ring extension reactions. However, the synthesis of functionalized silacyclobutanes remains an unmet challenge because of the limited functional group tolerance of the reactions with organometallic reagents and chlorosilacyclobutanes. Herein, we report a conceptually different solution to this end through a visible-light-induced metal-free hydrosilylation of unactivated alkenes with hydrosilacyclobutanes. A wide range of unactivated alkenes with diverse functional groups includ

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16

Sanzone, Jillian R., and K. A. Woerpel. "ChemInform Abstract: High Reactivity of Strained Seven-Membered-Ring trans-Alkenes." ChemInform 47, no. 21 (2016). http://dx.doi.org/10.1002/chin.201621212.

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17

Chen, Xin, Chen Yang, Yun-Fei Bai, et al. "Branched‐Selective Functionalization of 2‐Alkyl Aziridines through Ni‐Catalyzed Dynamic Kinetic Activation." Angewandte Chemie International Edition, June 23, 2025. https://doi.org/10.1002/anie.202505625.

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Overriding the inherent substrate‐controlled regioselectivity in aziridine activation holds significant potential. It could enable previously inaccessible disconnections from these readily available, strained heterocycles, facilitating the diverse synthesis of nitrogen‐containing products. In this study, we present a Ni‐catalyzed dynamic kinetic activation of 2‐alkyl (and 2,2‐dialkyl) aziridines, leading to unconventional branched‐selective alkyl Heck‐type coupling with styrenes and reductive defluorinative coupling with trifluoromethyl alkenes. In addition to enabling the functionalization of

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18

Chen, Xin, Chen Yang, Yun-Fei Bai, et al. "Branched‐Selective Functionalization of 2‐Alkyl Aziridines through Ni‐Catalyzed Dynamic Kinetic Activation." Angewandte Chemie, June 23, 2025. https://doi.org/10.1002/ange.202505625.

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Overriding the inherent substrate‐controlled regioselectivity in aziridine activation holds significant potential. It could enable previously inaccessible disconnections from these readily available, strained heterocycles, facilitating the diverse synthesis of nitrogen‐containing products. In this study, we present a Ni‐catalyzed dynamic kinetic activation of 2‐alkyl (and 2,2‐dialkyl) aziridines, leading to unconventional branched‐selective alkyl Heck‐type coupling with styrenes and reductive defluorinative coupling with trifluoromethyl alkenes. In addition to enabling the functionalization of

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19

Xu, Sangxuan, Yulu Zhou, Hanliang Zheng, and Gangguo Zhu. "4‐Exo‐Trig Radical Cyclization: A Promising Approach to Four‐Membered Rings." Chemistry – A European Journal, February 25, 2025. https://doi.org/10.1002/chem.202500206.

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The 4‐exo‐trig radical cyclization represents a formidable challenge owing to the unfavorable thermodynamics associated with the formation of highly strained four‐membered rings. Stimulated by the explosive advancements of radical chemistry over the past decades, significant progresses have been made in this area, including the SmI2‐mediated 4‐exo‐trig carbonyl‐alkene cyclization, n‐Bu3SnH‐mediated 4‐exo cyclization of functionalized alkenes or alkynes, transition metal‐catalyzed 4‐exo‐trig ring closures, and visible light‐induced 4‐exo‐trig cyclization cascade, providing efficient protocols t

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20

Smyth, Megan, Thomas S. Moody, Scott Wharry, and Marcus Baumann. "Continuous Flow Synthesis of Cyclobutenes Using LED Technology." Synlett, May 4, 2023. http://dx.doi.org/10.1055/a-2086-0630.

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Cyclobutenes are highly strained ring systems of considerable synthetic interest that can be accessed via cycloaddition reactions between alkenes and alkynes. However, their traditional preparation relies on photochemical [2+2]-cycloadditions that exploit low wavelength UV radiation emitted from inefficient medium-pressure Hg-lamps. This paper reports on the development of a modern approach using a high-power LED set-up emitting at the boundary of UV-A and visible light in conjunction with a continuous flow reactor. The resulting flow process renders a series of cyclobutenes from maleimides an

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21

Dupeux, Auréllien, A. Truchon, E. Gentilini, and Veronique MICHELET. "Gold- and Platinum-Catalyzed Prins-Type [2+2+2]-cycloadditions: From Original Methods to Applications." Synthesis, June 26, 2025. https://doi.org/10.1055/a-2644-2089.

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This review presents recent advances in gold- and platinum-catalyzed [2+2+2] cyclization involving an alkyne (or an allene), an alkene, and a carbonyl compound. These transformations are referred to as Prins-type cyclization, by analogy with the classical Prins reaction, in which an alkene reacts with an oxonium species derived from a carbonyl compound. In the metal-catalyzed versions, the carbonyl engages with a metal carbene intermediate—either directly at the carbene center or at another electrophilic site within a strained ring (e.g., cyclopropane or cyclobutane)—to generate an oxonium spe

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22

Du, Yuhui, Yang Yang, Peter Deglmann, Thomas W. Holcombe, Yifeng Du, and E. Bryan Coughlin. "The competition between radical copolymerization and charge separation of cyclic ketene acetals and electron‐deficient olefins." Journal of Polymer Science, September 15, 2023. http://dx.doi.org/10.1002/pol.20230480.

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AbstractCyclic ketene acetals (CKAs) possess unique features in two aspects. On one hand, after the addition of a radical on the alkene, CKAs can undergo ring‐opening via radical rearrangement, enabling polyester preparation based on chain‐growth polymerization. On the other hand, the alkene connected with two electron‐donating oxygens in a strained form exhibit unique reactivities, resulting in complex reactions in the presence of electron deficient compounds. In this investigation, fundamental studies on CKA radical ring‐opening polymerization and charge‐mediated reactions were performed. Al

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23

Liu, Zining, Yandong Wang, Jiahui Yu, Huanfeng Jiang, Minyan Wang, and Liangbin Huang. "Nickel‐Catalyzed Cross‐Electrophile Coupling to Access Polysubstituted Cyclobutenes." Angewandte Chemie, May 13, 2025. https://doi.org/10.1002/ange.202507087.

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The synthesis of cyclobutene remains inefficient due to inherent ring strain and poor regioselectivity. We demonstrate here a nickel‐catalyzed cross‐electrophile coupling (XEC) between readily accessible homopropargyl halides and commercially available aryl/vinyl electrophiles for the direct access to polysubstituted cyclobutenes. This approach provides the first reductive 4‐endo‐dig cyclization with high chemo‐ and regioselectivity, which paves the way for synthesis of diverse cyclobutene containing compounds (including synthetically challenging macrocycles). The synthesis of antitumor‐active

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24

Liu, Zining, Yandong Wang, Jiahui Yu, Huanfeng Jiang, Minyan Wang, and Liangbin Huang. "Nickel‐Catalyzed Cross‐Electrophile Coupling to Access Polysubstituted Cyclobutenes." Angewandte Chemie International Edition, May 13, 2025. https://doi.org/10.1002/anie.202507087.

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The synthesis of cyclobutene remains inefficient due to inherent ring strain and poor regioselectivity. We demonstrate here a nickel‐catalyzed cross‐electrophile coupling (XEC) between readily accessible homopropargyl halides and commercially available aryl/vinyl electrophiles for the direct access to polysubstituted cyclobutenes. This approach provides the first reductive 4‐endo‐dig cyclization with high chemo‐ and regioselectivity, which paves the way for synthesis of diverse cyclobutene containing compounds (including synthetically challenging macrocycles). The synthesis of antitumor‐active

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25

Giri, Rahul, Po-Kai Peng, Anthony J. Fernandes, Shijin Yu, Julian West, and Dmitry Katayev. "Overcoming Challenges in Small‐Ring Transfer: Direct Decarboxylative Hydroalkylation of Alkenes via Iron‐Thiol Catalysis." Angewandte Chemie, June 24, 2025. https://doi.org/10.1002/ange.202508377.

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Cyclopropanes, especially those substituted with trifluoromethyl (CF3) groups, are valuable scaffolds in medicinal chemistry. Their enhanced bioavailability contributes to the widespread presence of this motif in a variety of bioactive compounds. Despite the development of multiple synthetic strategies, a direct method for transferring CF3‐containing small rings from their most abundant carboxylic acid surrogates remains a significant challenge. In this work, we overcome the challenging decarboxylation of CF3‐cyclopropyl and CF3‐cyclobutyl carboxylic acids while leveraging the ligand‐to‐metal

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26

Giri, Rahul, Po-Kai Peng, Anthony J. Fernandes, Shijin Yu, Julian West, and Dmitry Katayev. "Overcoming Challenges in Small‐Ring Transfer: Direct Decarboxylative Hydroalkylation of Alkenes via Iron‐Thiol Catalysis." Angewandte Chemie International Edition, June 24, 2025. https://doi.org/10.1002/anie.202508377.

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Cyclopropanes, especially those substituted with trifluoromethyl (CF3) groups, are valuable scaffolds in medicinal chemistry. Their enhanced bioavailability contributes to the widespread presence of this motif in a variety of bioactive compounds. Despite the development of multiple synthetic strategies, a direct method for transferring CF3‐containing small rings from their most abundant carboxylic acid surrogates remains a significant challenge. In this work, we overcome the challenging decarboxylation of CF3‐cyclopropyl and CF3‐cyclobutyl carboxylic acids while leveraging the ligand‐to‐metal

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27

Moradi, Hanieh, R. Govindarajan, Huy Gia Nguyen, et al. "Synthesis and Aerobic Oxidation of Perfluoroalkyl d10 Metal Complexes Supported by 2,7‐Dimethyl‐1,8‐naphthyridine." European Journal of Inorganic Chemistry, May 23, 2024. http://dx.doi.org/10.1002/ejic.202400257.

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The coordination chemistry of 2,7‐dimethyl‐1,8‐naphthyridine has been explored with perfluoroalkyl d10 metals, CuI, ZnII, and AgI. This ligand was shown to form dicoordinate CuI and AgI mono‐perfluoroalkyl complexes where naphthyridine coordinates with only one N‐donor, while bidentate coordination with both N‐atoms was observed in Zn bis(perfluoroalkyl) complexes forming a strained four‐membered chelate ring. Copper complexes undergo facile oxidation in the presence of air or excess O2 to give tetracoordinate CuII complexes coordinated to perfluorocarboxylates formed by oxygenation of the met

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