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Journal articles on the topic 'Alkyne functionalization reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Ouyang, Xuan-Hui, Yang Li, Ren-Jie Song, Ming Hu, Shenglian Luo, and Jin-Heng Li. "Intermolecular dialkylation of alkenes with two distinct C(sp3)─H bonds enabled by synergistic photoredox catalysis and iron catalysis." Science Advances 5, no. 3 (2019): eaav9839. http://dx.doi.org/10.1126/sciadv.aav9839.

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The functionalization of unactivated C(sp3)─H bonds represents one of the most powerful and most atom-economical tools for the formation of new carbon-based chemical bonds in synthesis. Although cross-dehydrogenative coupling reactions of two distinct C─H bonds for the formation of carbon-carbon bonds have been well investigated, controlled functionalizations of two or more different C(sp3)─H bonds across a functional group or a molecule (e.g., an alkene or alkyne) in a single reaction remain challenging. Here, we present a three-component dialkylation of alkenes with common alkanes and 1,3-di

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2

Martins, Guilherme M., Bahareh Shirinfar, Tomas Hardwick, Ayesha Murtaza, and Nisar Ahmed. "Organic electrosynthesis: electrochemical alkyne functionalization." Catalysis Science & Technology 9, no. 21 (2019): 5868–81. http://dx.doi.org/10.1039/c9cy01312a.

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3

Trigoura, Leslie, Yalan Xing, and Bhanu P. S. Chauhan. "Recyclable Catalysts for Alkyne Functionalization." Molecules 26, no. 12 (2021): 3525. http://dx.doi.org/10.3390/molecules26123525.

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In this review, we present an assessment of recent advances in alkyne functionalization reactions, classified according to different classes of recyclable catalysts. In this work, we have incorporated and reviewed the activity and selectivity of recyclable catalytic systems such as polysiloxane-encapsulated novel metal nanoparticle-based catalysts, silica–copper-supported nanocatalysts, graphitic carbon-supported nanocatalysts, metal organic framework (MOF) catalysts, porous organic framework (POP) catalysts, bio-material-supported catalysts, and metal/solvent free recyclable catalysts. In add

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4

Wilger, Dale J., Sydney E. Bottcher, and Lauren E. Hutchinson. "Nickel-Catalyzed anti-Selective Alkyne Functionalization Reactions." Synthesis 52, no. 19 (2020): 2807–20. http://dx.doi.org/10.1055/s-0040-1707885.

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Nickel-catalyzed anti-selective alkyne functionalization reactions are reviewed with an emphasis on the mechanisms that lead to their observed stereoselectivity. Since the isomerization of alkenylnickel species plays a key role in a large number of these reactions, the potential mechanisms for these processes are also described in detail.1 Introduction2 anti-Selective Hydroarylation3 anti-Selective Carboborylation4 anti-Selective Dicarbofunctionalization4.1 Carbocyanative Cyclization4.2 Cyclization with Aryl Donors4.3 Cyclization with CO2 4.4 Intermolecular Dicarbofunctionalization5 anti-Selec

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5

Manova, Radostina, Teris A. van Beek, and Han Zuilhof. "Surface Functionalization by Strain-Promoted Alkyne-Azide Click Reactions." Angewandte Chemie International Edition 50, no. 24 (2011): 5428–30. http://dx.doi.org/10.1002/anie.201100835.

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6

Yataka, Yusuke, Toshiki Sawada, and Takeshi Serizawa. "Enzymatic synthesis and post-functionalization of two-dimensional crystalline cellulose oligomers with surface-reactive groups." Chemical Communications 51, no. 63 (2015): 12525–28. http://dx.doi.org/10.1039/c5cc04378f.

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Two-dimensional crystalline cellulose oligomers with surface-reactive azide groups were synthesized by enzymatic reactions and covalently post-functionalized with alkyne-containing dye molecules through click reactions.

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7

Sahoo, Laxminarayan, Anadi Singhamahapatra, and Satyanarayan Sahoo. "Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization." Journal of the Serbian Chemical Society 83, no. 5 (2018): 539–48. http://dx.doi.org/10.2298/jsc170905030s.

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A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazoline protected sugar derivatives. The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation. The oxazoline protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used. T

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8

Cheng, Gang, Reyna K. V. Lim, Carlo P. Ramil, and Qing Lin. "Storable N-phenylcarbamate palladacycles for rapid functionalization of an alkyne-encoded protein." Chem. Commun. 50, no. 79 (2014): 11679–82. http://dx.doi.org/10.1039/c4cc02969k.

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Here we report the synthesis of storableN-phenylcarbamate palladacycles that showed robust reactivity in the cross-coupling reactions with an alkyne-encoded protein with a second-order rate constant approaching 19 770 ± 930 M<sup>−1</sup>s<sup>−1</sup>.

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9

Faragher, Robert J., Craig S. McKay, Xuyen D. Hoa, et al. "Functionalizing poly(cyclic olefins) using copper-catalyzed azide–alkyne “click” reactions." Canadian Journal of Chemistry 89, no. 5 (2011): 608–15. http://dx.doi.org/10.1139/v11-015.

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A robust method for functionalizing poly(cyclic olefin) surfaces comprised of Zeonor 1060R was developed. These surfaces were first oxidized using two separate methods, ozonolysis and oxygen plasma treatment, to increase their hydrophilic properties and produce carboxylic acids on the surface. The resulting acids enabled direct amide coupling with various amines containing azide or alkyne moieties onto the surface. These modified surfaces were further functionalized via copper-catalyzed azide–alkyne cycloadditions (CuAAC) on the surface and the method was optimized for this material. Surface m

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10

Eddahmi, Mohammed, Nuno M. M. Moura, Latifa Bouissane, et al. "A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions." Molecules 25, no. 1 (2019): 126. http://dx.doi.org/10.3390/molecules25010126.

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The alkylation of a series of nitroindazole derivatives with 1,2-dibromoethane afforded the corresponding N-(2-bromoethyl)- and N-vinyl-nitro-1H-indazoles. The Cu(I)-catalysed azide- alkyne 1,3-dipolar cycloaddition was selected to substitute the nitroindazole core with 1,4-disubstituted triazole units after converting one of the N-(2-bromoethyl)nitroindazoles into the corresponding azide. The reactivity in 1,3-dipolar cycloaddition reactions with nitrile imines generated in situ from ethyl hydrazono-α-bromoglyoxylates was studied with nitroindazoles bearing a vinyl unit. The corresponding nit

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11

Rahman, Md Shafiqur, and Naohiko Yoshikai. "Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations." Beilstein Journal of Organic Chemistry 16 (March 27, 2020): 524–29. http://dx.doi.org/10.3762/bjoc.16.48.

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The synthesis of triphenylene-fused phosphole oxides has been achieved through two distinct C–H functionalization reactions as key steps. The phosphole ring was constructed by a three-component coupling of 3-(methoxymethoxy)phenylzinc chloride, an alkyne, and dichlorophenylphosphine, involving the regioselective C–H activation of the C2 position of the arylzinc intermediate via 1,4-cobalt migration. The resulting 7-hydroxybenzo[b]phosphole derivative was used for further π-extension through Suzuki–Miyaura couplings and a Scholl reaction, the latter closing the triphenylene ring. The absorption

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12

Aridi, Toufic, and Mario Gauthier. "Synthesis of Arborescent Polymers by “Click” Grafting." MRS Proceedings 1613 (2014): 23–31. http://dx.doi.org/10.1557/opl.2014.154.

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ABSTRACTA novel method was developed for the preparation of arborescent (dendritic graft) polymers, by successive grafting reactions of linear chain segments using alkyne-azide “click” chemistry coupling. A linear polystyrene substrate was thus randomly functionalized with acetylene functionalities, by acetylation and further reaction with propargyl bromide in the presence of potassium hydroxide and 18-crown-6 in toluene. The anionic polymerization of styrene was achieved with 6-tert-butyldimethylsiloxy-hexyllithium to obtain polystyrene with a protected hydroxyl chain end. Deprotection of the

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13

Guram, Anil S., and Richard F. Jordan. "Alkene and alkyne insertion reactions of cationic Cp2Zr(.eta.2-pyridyl)(L)+ complexes. Zirconium-mediated functionalization of pyridines." Organometallics 10, no. 10 (1991): 3470–79. http://dx.doi.org/10.1021/om00056a016.

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14

Dadfar, Seyed Mohammad Mahdi, Sylwia Sekula-Neuner, Uwe Bog, Vanessa Trouillet, and Michael Hirtz. "Site-Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide-Alkyne and Thiol-Alkyne Click Chemistry Reactions." Small 14, no. 21 (2018): 1800131. http://dx.doi.org/10.1002/smll.201800131.

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15

Teichert, Johannes F., and Lea T. Brechmann. "Catch It If You Can: Copper-Catalyzed (Transfer) Hydrogenation Reactions and Coupling Reactions by Intercepting Reactive Intermediates Thereof." Synthesis 52, no. 17 (2020): 2483–96. http://dx.doi.org/10.1055/s-0040-1707185.

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The key reactive intermediate of copper(I)-catalyzed alkyne semihydrogenations is a vinylcopper(I) complex. This intermediate can be exploited as a starting point for a variety of trapping reactions. In this manner, an alkyne semihydrogenation can be turned into a dihydrogen-mediated coupling reaction. Therefore, the development of copper-catalyzed (transfer) hydrogenation reactions is closely intertwined with the corresponding reductive trapping reactions. This short review highlights and conceptualizes the results in this area so far, with H2-mediated carbon–carbon and carbon–heteroatom bon

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16

Böser, Richard, Lars Denker, and René Frank. "N-Heterocyclic Carbene Adducts of Alkynyl Functionalized 1,3,2-Dithioborolanes." Molecules 24, no. 9 (2019): 1690. http://dx.doi.org/10.3390/molecules24091690.

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Alkynyl functionalized boron compounds are versatile intermediates in the areas of medicinal chemistry, materials science, and optical materials. In particular, alkynyl boronate esters [R1−C≡C−B(OR2)2] are of interest since they provide reactivity at both the alkyne entity, with retention of the B−C bond or alkyne transfer to electrophilic substrates with scission of the latter. The boron atom is commonly well stabilized due to (i) the extraordinary strength of two B−O bonds, and (ii) the chelate effect exerted by a bifunctional alcohol. We reasoned that the replacement of a B−O for a B−S bond

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17

Li, Zhen, Yongqiang Dong, Anjun Qin, et al. "Functionalization of Disubstituted Polyacetylenes through Polymer Reactions: Syntheses of Functional Poly(1-phenyl-1-alkyne)s." Macromolecules 39, no. 2 (2006): 467–69. http://dx.doi.org/10.1021/ma051907q.

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18

Constant, Céline, Steeve Albert, Nicolas Zivic, Krystyna Baczko, Hélène Fensterbank, and Emmanuel Allard. "Orthogonal functionalization of a fullerene building block through copper-catalyzed alkyne–azide and thiol–maleimide click reactions." Tetrahedron 70, no. 18 (2014): 3023–29. http://dx.doi.org/10.1016/j.tet.2014.02.086.

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19

Iehl, Julien, and Jean-François Nierengarten. "Sequential copper catalyzed alkyne–azide and thiol–ene click reactions for the multiple functionalization of fullerene hexaadducts." Chemical Communications 46, no. 23 (2010): 4160. http://dx.doi.org/10.1039/c0cc00252f.

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20

Zhang, Fulin, Luoting Xin, Saihu Liao, Xueliang Huang, and Yinghua Yu. "Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents." Synthesis 53, no. 02 (2020): 238–54. http://dx.doi.org/10.1055/s-0040-1707268.

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AbstractTransition-metal-catalyzed direct inert C–H bond functionalization has attracted much attention over the past decades. However, because of the high strain energy of the suspected palladacycle generated via C–H bond palladation, direct functionalization of a C–H bond less than a three-bond distance from a catalyst center is highly challenging. In this short review, we summarize the advances on palladium-catalyzed bridging C–H activation, in which an inert proximal C–H bond palladation is promoted by the elementary step of migratory insertion of an alkene, an alkyne or a metal carbene in

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21

Odrobińska, Justyna, and Dorota Neugebauer. "Micellar Carriers Based on Amphiphilic PEG/PCL Graft Copolymers for Delivery of Active Substances." Polymers 12, no. 12 (2020): 2876. http://dx.doi.org/10.3390/polym12122876.

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Amphiphilic copolymers of alkyne functionalized 2-hydroxyethyl methacrylate (AlHEMA) and poly(ethylene glycol) methyl ether methacrylate (MPEGMA) with graft or V-shaped graft topologies were synthesized. The functionalization of poly(ε-caprolactone) (PCL) with azide group enabled attachment to P(AlHEMA-co-MPEGMA) copolymers via a “click” alkyne-azide reaction. The introduction of PCL as a second side chain type in addition to PEG resulted in heterografted copolymers with modified properties such as biodegradability. “Click” reactions were carried out with efficiencies between 17–70% or 32–50%

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22

Sousa, Joana L. C., Carmen S. R. Freire, Armando J. D. Silvestre, and Artur M. S. Silva. "Recent Developments in the Functionalization of Betulinic Acid and Its Natural Analogues: A Route to New Bioactive Compounds." Molecules 24, no. 2 (2019): 355. http://dx.doi.org/10.3390/molecules24020355.

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Betulinic acid (BA) and its natural analogues betulin (BN), betulonic (BoA), and 23-hydroxybetulinic (HBA) acids are lupane-type pentacyclic triterpenoids. They are present in many plants and display important biological activities. This review focuses on the chemical transformations used to functionalize BA/BN/BoA/HBA in order to obtain new derivatives with improved biological activity, covering the period since 2013 to 2018. It is divided by the main chemical transformations reported in the literature, including amination, esterification, alkylation, sulfonation, copper(I)-catalyzed alkyne-a

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23

Petko, Dina, Samuel Koh, and William Tam. "Transition Metal-Catalyzed Reactions of Alkynyl Halides." Current Organic Synthesis 16, no. 4 (2019): 546–82. http://dx.doi.org/10.2174/1570179416666190329200616.

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Background: Transition metal-catalyzed reactions of alkynyl halides are a versatile means of synthesizing a wide array of products. Their use is of particular interest in cycloaddition reactions and in constructing new carbon-carbon and carbon-heteroatom bonds. Transition metal-catalyzed reactions of alkynyl halides have successfully been used in [4+2], [2+2], [2+2+2] and [3+2] cycloaddition reactions. Many carbon-carbon coupling reactions take advantage of metal-catalyzed reactions of alkynyl halides, including Cadiot-Chodkiewicz, Suzuki-Miyaura, Stille, Kumada-Corriu and Inverse Sonogashira

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24

Carreiro, Elisabete P., Ana M. Sena, Adrián Puerta, José M. Padrón, and Anthony J. Burke. "Synthesis of Novel 1,2,3-Triazole-Dihydropyrimidinone Hybrids Using Multicomponent 1,3-Dipolar Cycloaddition (Click)–Biginelli Reactions: Anticancer Activity." Synlett 31, no. 06 (2020): 615–21. http://dx.doi.org/10.1055/s-0039-1690781.

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In this work, 21 novel (1,4-disubstituted 1,2,3-triazole)-dihydropyrimidinone (1,2,3-trzl-DHPM) type hybrids were synthesized and characterized. These were divided into two types: hybrids A (5 in total) containing the dihydropyrimidinone heterocyclic ring decorated with a 1,4-disubstituted 1,2,3-triazole in the C-5 position [these compounds were accessed by a multicomponent copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) (or click)–Biginelli reactions with satisfactory yields (39–57%)] and hybrids B (16 in total) containing two 1,2,3-triazole units in the C-5 and C-6 methyl position of

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25

Kavoosi, Sam, Ramanjaneyulu Rayala, Brenna Walsh, et al. "Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide–alkyne click reactions and direct C H bond functionalization." Tetrahedron Letters 57, no. 39 (2016): 4364–67. http://dx.doi.org/10.1016/j.tetlet.2016.08.053.

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26

Domena, Justin, Carlos Chong, Qiaxian Johnson, Bhanu Chauhan, and Yalan Xing. "Highly Efficient Recyclable Sol Gel Polymer Catalyzed One Pot Difunctionalization of Alkynes." Molecules 23, no. 8 (2018): 1879. http://dx.doi.org/10.3390/molecules23081879.

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Amino-bridged gel polymer P1 was discovered to catalyze alkyne halo-functionalization in excellent yields, regioselectivity, functional group compatibility, and recyclability. We have observed that both aromatic and aliphatic alkynes can be converted to α,α-dihalogenated ketones in the presence of polymer P1 under metal-free conditions at room temperature within a short reaction time.

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27

Vincent, Jean-Marc, Alain Rabion, Vittal K. Yachandra, and Richard H. Fish. "Fluorous biphasic catalysis. 2. Synthesis of fluoroponytailed amine ligands along with fluoroponytailed carboxylate synthons, [M(C8F17(CH2)2CO2)2] (M = Mn2+ or Co2+): Demonstration of a perfluoroheptane soluble precatalyst for alkane and alkene functionalization in the presence of tert-butyl hydroperoxide and oxygen gas." Canadian Journal of Chemistry 79, no. 5-6 (2001): 888–95. http://dx.doi.org/10.1139/v01-012.

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Fluorous biphasic catalysis (FBC) is a relatively new concept for homogeneous catalysis where the fluorocarbon soluble catalyst resides in a separate phase from the substrate and products. Therefore, separation of the catalyst and the products occurs by a facile decantation process. In this contribution, we present the synthesis of new Rf-fluoroponytailed synthons, 2-iodo-1-perfluorooctyl-3-propanol (1), 3-perfluorooctyl-1-propanol (2), and 3-perfluorooctyl-1-iodopropane (3), a variety of new Rf-fluoroponytailed ligands (48), with starting amines, 1,4,7-triazacyclononane, bis-picolylamine, an

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28

Suárez-Pantiga, Samuel, and José M. González. "Electrophilic activation of unsaturated systems: Applications to selective organic synthesis." Pure and Applied Chemistry 85, no. 4 (2013): 721–39. http://dx.doi.org/10.1351/pac-con-12-10-24.

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Selected examples from previous work on iodonium-triggered approaches for the functionalization of unsaturated systems, which summarize innovative transformations, are presented. This section is mostly focused on C–C bond-forming processes from alkynes that are directly bonded to relevant heteroatoms, such as iodine, silicon, or sulfur. Besides, recent advances related to iodonium-promoted C–H functionalization reactions are briefly outlined. A second section shows representative examples of our current research activity on electrophilic reactions aimed at the activation of unsaturated systems

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29

BILA, Evgenia, Daryna SOLTYS, and Mykola OBUSHAK. "THREE-COMPONENT REACTIONS OF UNSATURATED COMPOUNDS WITH ARENEDIASONIUM SALTS AND NEUTRAL NUCLEOPHILS. ARYLSULFONYLATION." Proceedings of the Shevchenko Scientific Society. Series Сhemical Sciences 2020, no. 60 (2020): 31–54. http://dx.doi.org/10.37827/ntsh.chem.2020.60.031.

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The results of recent achievements on the interaction of arenediazonium salts with unsaturated compounds in the presence of neutral nucleophiles are summarized. New examples of multicomponent transformations with the participation of such neutral nucleophiles as CO (arylcarbonylation), NO (arylnitrosylation), aceto¬nitrile (aminoarylation), SO2 (arylsulfonylation) and others are given. These reactions can be applied to alkenes, alkynes, aromatic compounds. Mild reaction conditions allow the use of reagents with different functional groups. Reactions of this type open up the possibility of one-

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30

Czekelius, Constantin, Lucas Helmecke, Michael Spittler, and Bernd M. Schmidt. "Metal-Free Iodoperfluoroalkylation: Photocatalysis versus Frustrated Lewis Pair Catalysis." Synthesis 53, no. 01 (2020): 123–34. http://dx.doi.org/10.1055/s-0040-1707232.

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A comparison of two catalytic, metal-free iodoperfluoroalkylation protocols is presented. Frustrated Lewis pairs [ t Bu3P/B(C6F5)3] or phosphines/phosphites under visible light irradiation efficiently mediate the functionalization of non-activated alkenes and alkynes. A comprehensive account of the corresponding substrate scopes as well as insights into the mechanistic details of both reaction pathways are provided.

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Qian, Zhen-Chao, Jun Zhou, Bo Li, Fang Hu, and Bing-Feng Shi. "Rh(iii)-catalyzed regioselective hydroarylation of alkynes via directed C–H functionalization of pyridines." Org. Biomol. Chem. 12, no. 22 (2014): 3594–97. http://dx.doi.org/10.1039/c4ob00612g.

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Rh(iii)-catalyzed C-3 selective alkenylation of pyridines via hydroarylation of alkynes has been developed. The reaction shows high regioselectivity, high yield and good functional group tolerance, providing a convenient strategy for the synthesis of trisubstituted alkenes.

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Jeyachandran, Rajkumar, Harish Kumar Potukuchi, and Lutz Ackermann. "Copper-catalyzed CuAAC/intramolecular C–H arylation sequence: Synthesis of annulated 1,2,3-triazoles." Beilstein Journal of Organic Chemistry 8 (October 16, 2012): 1771–77. http://dx.doi.org/10.3762/bjoc.8.202.

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Step-economical syntheses of annulated 1,2,3-triazoles were accomplished through copper-catalyzed intramolecular direct arylations in sustainable one-pot reactions. Thus, catalyzed cascade reactions involving [3 + 2]-azide–alkyne cycloadditions (CuAAC) and C–H bond functionalizations provided direct access to fully substituted 1,2,3-triazoles with excellent chemo- and regioselectivities. Likewise, the optimized catalytic system proved applicable to the direct preparation of 1,2-diarylated azoles through a one-pot C–H/N–H arylation reaction.

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DeLuca, Ryan J., Benjamin J. Stokes, and Matthew S. Sigman. "The strategic generation and interception of palladium-hydrides for use in alkene functionalization reactions." Pure and Applied Chemistry 86, no. 3 (2014): 395–408. http://dx.doi.org/10.1515/pac-2014-5041.

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Abstract We review methods that our lab has developed for the generation of Pd-hydrides and the manipulation of these useful intermediates via β-hydride elimination and migratory insertion steps. For a given alkene functionalization reaction, careful understanding of the dynamics of β-hydride elimination, migratory insertion, and transmetallation have allowed for the selective functionalization of Pd-alkyl intermediates. This has afforded us a means by which to transpose palladium to a desired position on a substrate for subsequent functionalization, empowering a number of useful C–H, C–O, and

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34

Singh, Keisham. "Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts." Catalysts 9, no. 2 (2019): 173. http://dx.doi.org/10.3390/catal9020173.

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The past decades have witnessed rapid development in organic synthesis via catalysis, particularly the reactions through C–H bond functionalization. Transition metals such as Pd, Rh and Ru constitute a crucial catalyst in these C–H bond functionalization reactions. This process is highly attractive not only because it saves reaction time and reduces waste,but also, more importantly, it allows the reaction to be performed in a highly region specific manner. Indeed, several organic compounds could be readily accessed via C–H bond functionalization with transition metals. In the recent past, trem

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35

Seath, Ciaran P., and Nathan T. Jui. "Intermolecular Reactions of Pyridyl Radicals with Olefins via Photoredox Catalysis." Synlett 30, no. 14 (2019): 1607–14. http://dx.doi.org/10.1055/s-0037-1611527.

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Pyridines are valuable motifs in a number of bioactive and functional molecules. The chemoselective functionalization of these structures from stable and widely available starting materials is a meaningful goal. We have demonstrated selective formation of pyridyl radicals at any position (2-, 3-, 4-pyridyl), through the action of a reducing photoredox catalyst. These radicals readily engage alkenes to deliver high-value products. Alteration of the reaction medium has enabled the use of a diverse range of alkene subtypes in a highly divergent and chemoselective manner.1 Introduction2 Minisci-Ty

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36

Popov, Stasik, Brian Shao, Alex L. Bagdasarian, et al. "Teaching an old carbocation new tricks: Intermolecular C–H insertion reactions of vinyl cations." Science 361, no. 6400 (2018): 381–87. http://dx.doi.org/10.1126/science.aat5440.

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Vinyl carbocations have been the subject of extensive experimental and theoretical studies over the past five decades. Despite this long history in chemistry, the utility of vinyl cations in chemical synthesis has been limited, with most reactivity studies focusing on solvolysis reactions or intramolecular processes. Here we report synthetic and mechanistic studies of vinyl cations generated through silylium–weakly coordinating anion catalysis. We find that these reactive intermediates undergo mild intermolecular carbon-carbon bond–forming reactions, including carbon-hydrogen (C–H) insertion i

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37

Vanhaecht, Stef, Jeroen Jacobs, Luc Van Meervelt, and Tatjana N. Parac-Vogt. "A versatile and highly efficient post-functionalization method for grafting organic molecules onto Anderson-type polyoxometalates." Dalton Transactions 44, no. 44 (2015): 19059–62. http://dx.doi.org/10.1039/c5dt03559g.

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38

Couture, Guillaume, Vincent Ladmiral, and Bruno Améduri. "Methods to prepare quaternary ammonium groups-containing alternating poly(chlorotrifluoroethylene-alt-vinyl ether) copolymers." RSC Advances 5, no. 14 (2015): 10243–53. http://dx.doi.org/10.1039/c4ra09238d.

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Quaternary ammonium groups-containing alternating poly(chlorotrifluoroethylene-alt-vinyl ether) copolymers were synthesized using post-polymerization functionalization methods such as azide–alkyne cycloaddition and cyclocarbonate–amine reaction.

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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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Hirose, Daisuke, and Tsuyoshi Taniguchi. "Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water." Beilstein Journal of Organic Chemistry 9 (August 20, 2013): 1713–17. http://dx.doi.org/10.3762/bjoc.9.196.

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Water induces a change in the product of radical multifunctionalization reactions of aliphatic alkenes involving an sp3 C–H functionalization by an 1,5-hydrogen shift using tert-butyl nitrite and molecular oxygen. The reaction without water, reported previously, gives nitrated γ-lactols, whereas the reaction in the presence of water produces 4-hydroxy-5-nitropentyl nitrate or 4-hydroxy-3-nitropentyl nitrate derivatives.

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Nierengarten, Jean-François. "Copper-catalyzed alkyne-azide cycloaddition for the functionalization of fullerene building blocks." Pure and Applied Chemistry 84, no. 4 (2011): 1027–37. http://dx.doi.org/10.1351/pac-con-11-08-21.

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In this paper, we report our ongoing progress in the preparation of fullerene-azide or fullerene-alkyne building blocks, allowing their further chemical transformation under the copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction conditions.

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Speyerer, Christian, Kirsten Borchers, Joachim Storsberg, Günter E. M. Tovar, Thomas Hirth, and Achim Weber. "Generation and Surface Functionalization of Electro Photographic Toner Particles for Biomaterial Applications." MRS Proceedings 1569 (2013): 165–71. http://dx.doi.org/10.1557/opl.2013.906.

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ABSTRACTIn this paper, we provide the investigation about the controlled surface functionalization of acrylic toner particles for electro photography (“laser printing”) with sodium hydroxide and the subsequent carbodiimide-mediated coupling of numerous functional amines onto the generated carboxylic group. Various chemically valuable functionalities, comprising of thiol, alkyne and azide, were bound onto the particles’ surface and allow for further versatile modifications via huisgen cycloaddition as well as thiol-ene reaction. The functionalization of the acrylic toner surface with alkyne, az

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Singh, Kuldeep, Kulbir Kulbir, Tarang Gupta, Rajneesh Kaur, and Raman Singh. "Applications of Rozen’s Reagent in Oxygen-Transfer and C–H Activation Reactions." Synthesis 51, no. 02 (2018): 371–83. http://dx.doi.org/10.1055/s-0037-1609638.

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Rozen’s reagent (hypofluorous acid–acetonitrile complex, HOF·MeCN) is a robust nonspecific oxygen-transfer reagent and became a proven tool for the oxidation of difficult-to-oxidize molecules. It has been applied to instant oxygen transfers to functional groups such as alkenes, alkynes, and aromatic hydrocarbons, epoxidation, oxidation of alcohols, amines, and alkynes, oxygen-transfer reactions with nitrogen, phosphorus, and sulfur-containing substrates, and α-hydroxylation of carbonyl groups. Apart from being a potential green oxidizing agent, the complex has applications in 18O-labeling and

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Bento, Marcos A., Sara Realista, Ana S. Viana, Ana M. Ferraria, and Paulo N. Martinho. "Cryptand-Functionalized Highly Oriented Pyrolytic Graphite Electrodes." Sustainability 13, no. 8 (2021): 4158. http://dx.doi.org/10.3390/su13084158.

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Reproducible materials that have detection properties towards a certain molecule are very important for applications in the fabrication of devices. Among all the substrates that are used, highly oriented pyrolytic graphite allows to clearly image a monolayer. On the other hand, cryptand molecules are versatile because they can sense certain analytes with high selectivity. The highly oriented pyrolytic graphite electrode was first functionalized with an aryl bearing a bromine or an alkyne group to further attach cryptand molecules to its surface. The functionalization was performed through the

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Warneke, Jonas, Martin Mayer, Markus Rohdenburg, et al. "Direct functionalization of C−H bonds by electrophilic anions." Proceedings of the National Academy of Sciences 117, no. 38 (2020): 23374–79. http://dx.doi.org/10.1073/pnas.2004432117.

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Alkanes and [B12X12]2−(X = Cl, Br) are both stable compounds which are difficult to functionalize. Here we demonstrate the formation of a boron−carbon bond between these substances in a two-step process. Fragmentation of [B12X12]2−in the gas phase generates highly reactive [B12X11]−ions which spontaneously react with alkanes. The reaction mechanism was investigated using tandem mass spectrometry and gas-phase vibrational spectroscopy combined with electronic structure calculations. [B12X11]−reacts by an electrophilic substitution of a proton in an alkane resulting in a B−C bond formation. The

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Hjerrild, Per, Thomas Tørring, and Thomas B. Poulsen. "Dehydration reactions in polyfunctional natural products." Natural Product Reports 37, no. 8 (2020): 1043–64. http://dx.doi.org/10.1039/d0np00009d.

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Here, we review methods for chemical dehydration of alcohols to alkenes and discuss the potential of late-stage functionalization by direct, site- and chemo-selective dehydration of complex molecular substrates.

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Wang, Chuan, and Youxiang Jin. "Nickel-Catalyzed Asymmetric Cross-Electrophile Coupling Reactions." Synlett 31, no. 19 (2020): 1843–50. http://dx.doi.org/10.1055/s-0040-1707216.

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The merger of cross-electrophile coupling and asymmetric catalysis provides a novel approach to the preparation of optically active compounds. This method is often endowed with high step economy, mild conditions, and excellent tolerance of functional groups. Recent advances in the research field of nickel-catalyzed asymmetric cross-electrophile coupling reactions are highlighted in this concise Synpacts article.1 Introduction2 Asymmetric Cross-Electrophile Coupling Reactions between Organohalides3 Asymmetric Electrophilic Ring-Opening Reactions4 Asymmetric Electrophilic Difunctionalization of

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Li, Xiang, Pinhong Chen, and Guosheng Liu. "Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes." Beilstein Journal of Organic Chemistry 14 (July 18, 2018): 1813–25. http://dx.doi.org/10.3762/bjoc.14.154.

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Hypervalent iodine(III) reagents have been well-developed and widely utilized in functionalization of alkenes, however, generally either stoichiometric amounts of iodine(III) reagents are required or stoichiometric oxidants such as mCPBA are employed to in situ generate iodine(III) species. In this review, recent developments of hypervalent iodine(III)-catalyzed functionalization of alkenes and asymmetric reactions using a chiral iodoarene are summarized.

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Anancharoenwong, Ekasit, Jean Francois Pilard, Irène Campistron, Albert Laguerre, Frédéric Gohier, and Sophie Bistac. " Preparation of New Polyols Based on Cis-1,4-Polyisoprene by Using 1,3-Dipolar Cycloaddition." Advanced Materials Research 844 (November 2013): 381–84. http://dx.doi.org/10.4028/www.scientific.net/amr.844.381.

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This research focuses on synthesis and modification of polyol precursors derived from cis-1,4-polyisoprene (PI). These new polyol precursors can be converted to high value-added polyurethane (PU). The epoxidized hydroxytelechelic PI (EHTPI) prepared by chemical modification from PI was used as starting material for polyol synthesis. 1,3-Dipolar cycloaddition between a terminal alkyne and an azide has rapidly become the most popular click reaction. We applied this reaction to couple azide-functionalized PI and alkyne-functionalized sugar for preparing polyols. For azide functionalization, 1-met

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Gevrek, Tugce Nihal, Aysun Degirmenci, Rana Sanyal, and Amitav Sanyal. "Multifunctional and Transformable ‘Clickable’ Hydrogel Coatings on Titanium Surfaces: From Protein Immobilization to Cellular Attachment." Polymers 12, no. 6 (2020): 1211. http://dx.doi.org/10.3390/polym12061211.

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Multifunctionalizable hydrogel coatings on titanium interfaces are useful in a wide range of biomedical applications utilizing titanium-based materials. In this study, furan-protected maleimide groups containing multi-clickable biocompatible hydrogel layers are fabricated on a titanium surface. Upon thermal treatment, the masked maleimide groups within the hydrogel are converted to thiol-reactive maleimide groups. The thiol-reactive maleimide group allows facile functionalization of these hydrogels through the thiol-maleimide nucleophilic addition and Diels–Alder cycloaddition reactions, under

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