Relevant bibliographies by topics / Hydroalkoxylation

Academic literature on the topic 'Hydroalkoxylation'

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Published: 4 June 2021
Last updated: 19 February 2022

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Journal articles on the topic "Hydroalkoxylation"

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Li, Zhi, and Wen-Bin Xie. "Asymmetric Synthesis of Ethers by Catalytic Alkene Hydro­alkoxy­lation." Synthesis 52, no. 15 (April 14, 2020): 2127–46. http://dx.doi.org/10.1055/s-0039-1690874.

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Many chiral ethers have important physiological activities. Although many asymmetric hydroalkoxylations of olefins with alcohols or phenols have been developed to make chiral ethers, challenges still remain in achieving high reactivity and selectivity over an ever-increasing diversity of alkenes and alcohols. In this review, recent developments on catalytic asymmetric alkene hydroalkoxylations are summarized based on the substitution patterns of alkenes.1 Introduction2 Asymmetric Hydroalkoxylation of Non-Activated Alkenes2.1 Intramolecular Additions2.2 Intermolecular Additions3 Asymmetric Hydroalkoxylation of Enol Ethers3.1 Intramolecular Additions3.2 Intermolecular Additions4 Asymmetric Hydroalkoxylation of α,β-Unsaturated Carbonyl Compounds4.1 α,β-Unsaturated Ketones and Aldehydes as Substrates4.2 α,β-Unsaturated Esters, Amides and Carboxylic Acids as Substrates5 Asymmetric Hydroalkoxylation of Allenes5.1 Intramolecular Additions5.2 Intermolecular Additions6 Conclusion
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Kena Diba, Anastasie, Jeanne-Marie Begouin, and Meike Niggemann. "Calcium catalyzed hydroalkoxylation." Tetrahedron Letters 53, no. 49 (December 2012): 6629–32. http://dx.doi.org/10.1016/j.tetlet.2012.08.129.

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Nishina, Naoko, and Yoshinori Yamamoto. "Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination." Tetrahedron Letters 49, no. 33 (August 2008): 4908–11. http://dx.doi.org/10.1016/j.tetlet.2008.05.152.

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Notar Francesco, Irene, Bastien Cacciuttolo, Mathieu Pucheault, and Sylvain Antoniotti. "Simple metal salts supported on montmorillonite as recyclable catalysts for intramolecular hydroalkoxylation of double bonds in conventional and VOC-exempt solvents." Green Chemistry 17, no. 2 (2015): 837–41. http://dx.doi.org/10.1039/c4gc01990c.

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Gao, Shu-Shan, Marc Garcia-Borràs, Joyann S. Barber, Yang Hai, Abing Duan, Neil K. Garg, K. N. Houk, and Yi Tang. "Enzyme-Catalyzed Intramolecular Enantioselective Hydroalkoxylation." Journal of the American Chemical Society 139, no. 10 (March 2017): 3639–42. http://dx.doi.org/10.1021/jacs.7b01089.

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Camacho, Drexel H., Itaru Nakamura, Shinichi Saito, and Yoshinori Yamamoto. "Palladium-Catalyzed Hydroalkoxylation of Methylenecyclopropanes." Angewandte Chemie International Edition 38, no. 22 (November 15, 1999): 3365–67. http://dx.doi.org/10.1002/(sici)1521-3773(19991115)38:22<3365::aid-anie3365>3.0.co;2-5.

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Cui, Dong-Mei, Zhi-Ling Zheng, and Chen Zhang. "Gold-Catalyzed Hydroalkoxylation of Alkoxyallenes." Journal of Organic Chemistry 74, no. 3 (February 6, 2009): 1426–27. http://dx.doi.org/10.1021/jo802513a.

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Diba, Anastasie Kena, Jeanne-Marie Begouin, and Meike Niggemann. "ChemInform Abstract: Calcium-Catalyzed Hydroalkoxylation." ChemInform 44, no. 13 (March 18, 2013): no. http://dx.doi.org/10.1002/chin.201313083.

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Notar Francesco, Irene, Bastien Cacciuttolo, Oana Pascu, Cyril Aymonier, Mathieu Pucheault, and Sylvain Antoniotti. "Simple salts of abundant metals (Fe, Bi, and Ti) supported on montmorillonite as efficient and recyclable catalysts for regioselective intramolecular and intermolecular hydroalkoxylation reactions of double bonds and tandem processes." RSC Advances 6, no. 24 (2016): 19807–18. http://dx.doi.org/10.1039/c5ra25176a.

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Gao, Erhui, Cheng Peng, Jingyi Zhang, Xiao-Na Wang, and Junbiao Chang. "Metal-free hydroalkoxylation of ynesulfonamides with esters." Organic & Biomolecular Chemistry 19, no. 10 (2021): 2182–85. http://dx.doi.org/10.1039/d0ob02575e.

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Dissertations / Theses on the topic "Hydroalkoxylation"

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Ferrand, Laura. "Hydrofonctionnalisations de liaisons multiples carbone-carbone catalysées par des complexes à base de métaux non nobles." Thesis, Paris 6, 2017. http://www.theses.fr/2017PA066348/document.

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Ce travail de thèse est consacré au développement de nouvelles méthodologies en catalyse mettant en jeu des complexes métalliques à base de métaux non nobles, en l’occurrence le cobalt et le niobium. Ces deux métaux ont été utilisés pour catalyser des réactions d’hydrofonctionnalisation de liaisons multiples carbone‒carbone. L’objectif était de proposer des systèmes catalytiques compétitifs à base de métaux non précieux et de promouvoir leur utilisation par rapport à d’autres métaux peu abondants et onéreux. Un complexe de cobalt bien défini, HCo(PMe3)4, a été employé pour catalyser des réactions d’hydroboration régio- et stéréosélectives d’alcynes internes, ainsi que des réactions de diboration d’alcynes. D’autre part, un système catalytique au niobium(V) cationique a été mis au point et utilisé pour diverses réactions d’hydrofonctionnalisation intramoléculaires, permettant la synthèse d’une large famille d’hétérocycles. De manière à mettre encore davantage en lumière ce métal et ces bienfaits, des travaux ont été réalisés en catalyse énantiosélective. Un système catalytique chiral de niobium(V) a été utilisé pour l’hydroalkoxylation d’alcènes énantiosélective. Des résultats encourageants ont été obtenus même si ce système doit encore être optimisé et testé en présence de différents hydroxyalcènes
This PhD work has focused on the development of new methodologies in catalysis based on non-noble metals: cobalt and niobium. These two metals have been used to catalyze hydrofunctionalization reactions of carbon‒carbon multiple bonds. The aim of those projects was to propose competitive catalytic systems based on non-precious metals and to promote their use compared to other rare and expensive metals. To this end, we successfully demonstrated that a well-defined cobalt complexe HCo(PMe3)4 is an efficient catalyst for regio- and stereoselective hydroboration reactions of internal alkynes, as well as diboration reactions. Also, a new catalytic system based on cationic niobium(V) has been developed and used to catalyze intramolecular hydrofunctionalization reactions leading to the synthesis of a large family of heterocycles. In order to reveal even more the potential of niobium in catalysis, we aimed to propose a chiral system able to catalyze enantioselective hydroalkoxylation of alkenes. Despite the promising results, some more efforts on the optimization of this system still need to be done
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Brinkmann, Christine. "Heavier group 2 metals : application to intermolecular hydroamination, C-F activation and intramolecular hydroalkoxylation." Thesis, Imperial College London, 2011. http://hdl.handle.net/10044/1/9155.

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This thesis describes the reactivity of different heavier alkaline earth catalysts [M{X(SiMe3)2}2(THF)n]m (M = Ca, Sr, Ba; X = N, CH; n= 0, 2; m= 1, 2) in the intermolecular hydroamination of styrene derivatives. The scope of these reactions with respect to the substrate was determined and detailed kinetic studies to establish rate law and temperature dependence of the hydroamination reactions reported were conducted. Overall, it was found that [Ca{N(SiMe3)2}2]2 is favoured enthalpically (Ca: ΔH‡ = 51 kJ∙mol-1, Sr: ΔH‡ = 71 kJ∙mol-1) however the corresponding strontium bis(amide) proved a significantly better catalyst, likely due to a favourably high entropy of activation value (Ca: ΔS‡ = -168 J/mol-1 ·K-1, Sr: ΔS‡ = -92 J∙mol-1∙K-1). Large kinetic isotope effects of 4.1 and 7.9 at 55 °C for the intermolecular hydroamination of styrene with piperidine mediated by [Ca{N(SiMe3)2}2]2 and [Sr{N(SiMe3)2}2]2, respectively, suggest a rate-determining alkene insertion into the M-N bond with immediate or concerted protonolysis. The methodology used in these hydroamination reactions was extended to simple dienes, diphenylacetylene and an activated enyne. The catalyst initiation of the metal bis(amides) with piperidine was shown to be reversible and the equilibrium constant solvent dependent. Novel calcium and strontium dialkyl complexes [M{CH(SiMe3)2}2(THF)2] (M= Ca, Sr) were used to overcome the problem of catalyst initiation and showed a different solvent dependence. An enhanced reactivity was found for the dialkyl complexes compared to the metal bis(amides). This increased reactivity allowed the application in new reactions such as the C-F activation of fluorobenzenes. Furthermore, the use of these catalytic systems was successfully extended to intramolecular hydroalkoxylation reactions of alkynyl alcohols in the formation of five- and six-membered enol ethers. In this case, [Ba{N(SiMe3)2}2]2 displayed significant reactivity although the “catalyst of choice” for these reactions proved to be strongly dependent on substrate substitution pattern. Through detailed kinetic studies the catalyst, substrate and temperature dependence of the cyclisation reaction were established and an unusual rate law with inverse substrate dependence proposed.
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Soklou, Kossi Efouako. "Synthèse d'hétérospirocycles par hydroaminations et hydroalkoxylations d'alcynes catalysées par l'or (I) - Méthodologie et application au développement de fragments spirocycliques pour la chimie médicinale." Thesis, Orléans, 2020. http://www.theses.fr/2020ORLE3066.

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Synthétiser des molécules azotées ou oxygénées spiro [4.5] ou spiro [5.5] possédant une liaison entre le carbone spiranique et l’atome d’azote ou d’oxygène reste un défi même si ces fragments sont représentés dans la nature et dans l’arsenal thérapeutique. Pour lever cette contrainte, nous avons développé une méthode générale de spirocyclisation catalysée par l’or (I) passant par des réactions d’hydroamination ou d’hydroalkoxylation d’alcynes. Dans la première partie de cette thèse, nous avons pu optimiser les conditions de spirocyclisation à base de JohnPhosAu(CH3CN)SbF6 en série azotée et oxygénée avec les alcynes vrais, puis accéder à des spirocycles tricycliques originaux par des réactions en cascade. Nous avons également démontré la robustesse de notre méthode vis-à-vis des composés chiraux. Dans la deuxième partie de ce travail, la méthode de spirocyclisation a été étendue aux alcynes disubstitués grâce au couple JohnPhosAuCl/AgNTf2. Dans la troisième partie, nous avons effectué la transformation des spirocycles afin d’accroître la diversité moléculaire. Pour ce faire, des réactions de Mizoroki-Heck intramoléculaires ont fourni des spirocycles tétracycliques originaux et stables tandis que d’autres réactions comme des réductions ont, en plus de la stabilité, accru leur tridimensionnalité. Avec tous ces fragments, un programme de chimie médicinale a été engagé et des actifs à motifs spirocycliques ont été élaborés comme inhibiteurs sélectifs de kinases
The synthesis of spiro [4.5] or [5.5] nitrogen or oxygen containing molecules with a bond between the carbon spirocenter and the nitrogen or oxygen atom remains a challenge, even if these fragments are represented in nature as well as in the therapeutic arsenal. To overcome this constraint, we have developed a general method of gold (I) catalyzed spirocyclization through the hydroamination or hydroalkoxylation of alkynes. In the first part of this thesis, we optimized spirocycle formation in both the nitrogen and oxygen series using conditions based on JohnPhosAu(CH3CN)SbF6 with unsubstituted alkynes. This also gave access to original tricyclic spirocycles by cascade reactions. We then demonstrated the robustness of our method with respect to chiral compounds. In the second part of this work, the spirocyclization method was extended to di-substituted alkynes using the combined JohnPhosAuCl/AgNTf2 catalyst. In the third part, we transformed our different spirocycles to increase molecular diversity. Intramolecular Mizoroki-Heck reactions provided original and stable tetracyclic spirocycles while other reactions such as double bond reduction increased both stability and 3D molecular space. With these fragments in hand, a medicinal chemistry program was initiated and spirocyclic compounds were developed as selective kinase inhibitors
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Carlino, Romain. "Réactions intramoléculaires de formation de liaison carbone – oxygène, sur des systèmes insaturés non activés, catalysées par des complexes de terres rares." Thesis, Université Paris-Saclay (ComUE), 2016. http://www.theses.fr/2016SACLS317.

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Ce travail de thèse s’est focalisé sur la formation de liaisons carbone-oxygène à partir d’alcènes et d’allènes non activés via des réactions intramoléculaires d’hydroalcoxylation ou d’hydroacylalcoxylation catalysées par des complexes de terres rares.Premièrement, la version racémique de ces réactions catalysées par deux systèmes différents a été étudiée : les tri-alkyls ainsi que les triflates de terres rares. Lors de cette étude, les différents effets stériques ou électroniques ainsi que les différentes substitutions sur l’insaturation ont été évalués. Pour les deux systèmes catalytiques, une sélectivité Markovnikov a été mise en évidence ; pour chacun de ces systèmes catalytiques deux mécanismes différents sont proposés. En effet, en plus des propriétés acide de Lewis, le fait que les alkyls de terres rares soient des bases de Brønsted, explique la différence de comportement catalytique des deux systèmes.Par la suite, ces réactions ont été étudiées dans leur version asymétrique. Pour cela, différents ligands chiraux ont été associés au triflate de scandium ; d’autre part, de nouveaux complexes mono-alkyl binaphtolate de terres rares dérivés des tri-alkyls ont également été synthétisés. Avec ces derniers, des éthers cycliques ont été obtenus avec des excès énantiomériques allant jusqu’à 34%.Etant donné que les triflates de terres rares ont montré une très bonne activité et que les mono-alkyl binaphtolates de scandium et d’yttrium ont conduit à d’encourageantes énantiosélectivités, il a été proposé de créer un nouveau complexe de terre rare muni de ligands chiraux associés par des liaisons ioniques ; les premiers essais de préparation de binaphtolate monotriflate de scandium et d’yttrium sont très prometteurs.Enfin, dans le cadre d’une collaboration, de nouveaux complexes de terres rares comportant des ligands dérivés de la BINAM ont été synthétisés et une étude RMN HMBC ¹H/¹ ⁵N a été réalisée afin de déterminer les différences forces de liaisons métal-azote. Ces complexes chiraux ont été notamment utilisés afin de mettre en évidence le concept de ligand relai avec la réalisation monotope de deux réactions métallocatalysée et organocatalysée consécutives
This thesis is focused on intramolecular carbon-oxygen bond formation of non-activated alkenes and allenes by hydroalkoxylation or hydroacylalkoxylation reactions catalyzed by rare earths complexes.Firstly, the racemic version of these reactions catalyzed by two different systems has been studied: tri-alkyls and triflate rare earth. In this study, different steric or electronic effects and different substitutions on insaturations have been evaluated. For both systems, Markovnikov selectivity was evidenced; two different mechanisms for each system have been proposed. Indeed, in addition to the Lewis acid properties, the fact that rare earth alkyls are also Brønsted bases, could explain the difference of catalytic behavior of these systems.Thereafter, enantioselective versions of these reactions have been studied. For that, different chiral ligands have been associated on scandium triflate; on the other hand, new mono-alkyl binaphtholate complexes from tri-alkyl complexes have been synthesized. Therewith, cyclic ethers have been obtained with enantiomeric excesses up to 34%.As triflate rare earths have shown an excellent activity and yttrium and scandium mono-alkyl binaphtholate led to encouraging enantioselectivity, it has been proposed to create a new rare earth complex with chiral ligand associated with ionic bonds; the first tests of scandium and yttrium binaphtholate monotriflate preparation are very promising.Finally, in the frame of a collaboration, new rare earth complexes bearing ligands derived from BINAM have been synthesized and a HMBC ¹H/¹ ⁵N NMR study have been realized to determine the strength of the different carbon-nitrogen bonds. These chiral complexes have been especially used to highlight the concept of relay ligand with one pot consequent metallocatalyzed and organocatalyzed reactions
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Paintner, Tobias [Verfasser], Florian [Akademischer Betreuer] Klappenberger, Florian [Gutachter] Klappenberger, and Sabine [Gutachter] Maier. "Novel Reaction Pathways through On-Surface Conditions: Tunneling-mediated Hydroalkoxylation and Gas-induced Deprotonation / Tobias Paintner ; Gutachter: Florian Klappenberger, Sabine Maier ; Betreuer: Florian Klappenberger." München : Universitätsbibliothek der TU München, 2019. http://d-nb.info/1187444057/34.

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Yang, Jing. "Synthèse et évaluation en catalyse asymétrique de nouveaux complexes de terres rares." Thesis, Paris 11, 2012. http://www.theses.fr/2012PA112381.

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Ce travail de thèse est dédié au développement des deux familles de complexes chiraux binaphtolates de terres rares et leur application en catalyse asymétrique dans les réactions d’addition de Michael, de Henry, de Strecker et d’hydroalkoxylation. La préparation d’une nouvelle famille de complexes chiraux bisbinaphtolates de terres rares a été optimisée. Ces nouveaux complexes ont été entièrement caractérisés grâce à des analyses RMN, IR, de spectroscopie de masse et des études de DRX de monocristaux isolés. Après une étude de stabilité, nous avons pu montrer que ces nouveaux complexes de terres rares peuvent être pesés à l’air libre et utilisés dans des réactions asymétriques sans dégazage des réactifs ni des solvants. Les comportements catalytiques de ces nouveaux complexes hétérobimétalliques ont été étudiés en détail dans des réactions énantiosélectives de Henry, de Strecker et d’addition de Michael. Une température d’isoinversion et un effet non linéaire ont notamment été mis en évidence dans la réaction d’addition de Michael de malonates sur des énones conduisant à des produits énantioenrichis avec des excès énantiomériques allant jusqu’à 83%. Une seconde famille de complexes monobinaphtolate monoalkyl de terres rares a été synthétisée et complètement caractérisée. Une structure DRX de ce type de complexe a pu être obtenue pour la première fois. Ces complexes ont été évalués dans des réactions de Strecker et d’hydroalkoxylation. Concernant cette dernière, la sélectivité a tout d’abord été étudiée avec ces complexes dans le cas des allènes et un mécanisme a pu être proposé. D’autre part, les premiers exemples d’hydroalkoxylation asymétrique d’alcènes, catalysés par ces complexes monobinaphtolate monoalkyl de terres rares, ont pu être décrits
This thesis is mainly devoted to the development of two families of rare earths chiral binaphtolate complex and their application in asymmetric catalysis such as Michael addition, Henry reaction, Strecker reaction and hydroalkoxylation reaction. At first, the preparation of a new family of rare earth bisbinaphtolate complexes has been optimized with complete characterizations including NMR, IR, mass spectroscopy and XRD studies on isolated single crystals. These new rare earths complexes are relative stable which can be used under air condition. The catalytic behavior of these new heterobimetallic complexes have been studied in detail: an isoinversion temperature was determined and the nonlinear effect was observed for asymmetric Michael additions of malonates on enones wich lead products with enantiomeric excess up to 83%. Secondly, a family of rare earth monobinaphtolate monoalkyl complexs has been synthesized and characterized. The first XRD structure of this family of complex was obtained. Steric substitutions of binaphtolate ligands on position 3,3’ have been proven to be essential for the formation of these complex. The selectivity of reaction of hydroalkoxylation of allene was studied with a proposed mechanism. First examples of asymmetric hydroalkoxylation of alkene catalyzed by rare earth complexes have been achieved by our rare earth monoalkyl monobinaphtolate complex
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Vuong, Khuong Quoc Chemistry Faculty of Science UNSW. "Metal complex catalysed C-X (X = S, O and N) bond formation." Awarded by:University of New South Wales. Chemistry, 2006. http://handle.unsw.edu.au/1959.4/23015.

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This thesis describes the catalysed addition of X-H bonds (X = S, O and N) to alkynes using a range of novel rhodium(I) and iridium(I) complexes containing hybrid bidentate phosphine-pyrazolyl, phosphine-imidazolyl and phosphine-N heterocyclic carbene (NHC) donor ligands. The synthesis of novel bidentate phosphine-pyrazolyl, phosphine-imidazolyl (P-N) and phosphine-NHC (PC) donor ligands and their cationic and neutral rhodium(I) and iridium(I) complexes [M(P N)(COD)]BPh4, [M(PC)(COD)]BPh4, [Ir(P-N)(CO)2]BPh4 and [M(P-N)(CO)Cl] were successfully performed. An unusual five coordinate iridium complex with phosphine-NHC ligands [Ir(PC)(COD)(CO)]BPh4 was also obtained. Seventeen single crystal X-ray structures of these new complexes were determined. A range of these novel rhodium and iridium complexes were effective as catalysts for the addition of thiophenol to a variety of alkynes. Iridium complexes were more effective than rhodium analogues. Cationic complexes were more effective than neutral complexes. Complexes with hybrid phosphine-nitrogen donor were more effective than complexes containing bidentate nitrogen donor ligands. An atom-economical, efficient method for the synthesis of cyclic acetals and bicyclic O,O-acetals was successfully developed based on the catalysed hydroalkoxylation. Readily prepared terminal and non-terminal alkyne diols were cyclised into bicyclic O,O-acetals in quantitative conversions in most cases. The efficiency of a range of rhodium and iridium complexes containing bidentate P-N and PC donor ligands as catalysts for the cyclisation of 4-pentyn-1-amine to 2-methyl-1-pyrroline varied significantly. The cationic iridium complexes with the bidentate phosphine-pyrazolyl ligands, [Ir(R2PyP)(COD)]BPh4 (2.39-2.42) were extremely efficient as catalysts for this transformation. Increasing the size of the substituent on or adjacent to the donor led to improvement in catalytic activity of the corresponding metal complexes. The mechanism of the catalysed hydroalkoxylation was proposed to proceed by the initial activation of the alkyne via ?? coordination to the metal centre. The ?? binding of both aliphatic and aromatic alkynes to [Ir(PyP)(CO)2]BPh4 (2.44) was observed by low temperature NMR and no reaction between 2.44 and alcohols was observed. In contrast, the facility in which thiol and amine oxidatively added to 2.44 led the proposal that in the hydrothiolation and hydroamination reaction, the catalytic cycle commences with the activation of the X-H bond (X = S, N) by an oxidative addition process.
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Ilg, Marina Kristina [Verfasser], Alois [Akademischer Betreuer] Fürstner, and Norbert [Gutachter] Krause. "Enantioinversion in der Gold(I)-katalysierten Hydroalkoxylierung von Allenen & Studien zur Totalsynthese von Chagosensine : Enantioinversion in the gold(I)-catalyzed hydroalkoxylation of allenes & studies toward the total synthesis of chagosensine / Marina Kristina Ilg ; Gutachter: Norbert Krause ; Betreuer: Alois Fürstner." Dortmund : Universitätsbibliothek Dortmund, 2017. http://d-nb.info/1128903466/34.

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Ella, Ndong Guy Judicaël. "Synthèses régiosélectives d'hétérocycles porteurs d'un groupement perfluoroalkyle." Thesis, Tours, 2015. http://www.theses.fr/2015TOUR4036/document.

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Dans ce travail, de nombreux hétérocycles porteurs d’un groupement CF3 ou C2F5 ont été décrits : des cétals, des benzo[1,3]dixoles, des pyran-2H-ones, des isocoumarines, des benzofuranes et des indolo[2,3-c]pyran-1-ones. Ces hétérocycles représentent une classe importante de produits biologiquement actifs. L’hydroalkoxylation intermoléculaire des dérivés du 4,4,4-perfluorobut-2-ynoate d’éthyle en présence d’une quantité catalytique de sodium métallique dans des conditions simples et douces a permis la synthèse de cétals fluorés d’une manière totalement régiosélective. La méthodologie a été étendue par la suite aux dérivés phénols pour préparer ,dans un premier temps, stériosélectivement des éthers d’énols. Des benzofuranes fluorées ont été synthétisées par la suite par cyclisation de quelques éthers vinyliques dans les conditions de Heck. Dans les mêmes conditions et en utilisant des dérivés du catéchol, nous avons réalisé des synthèses totalement régiosélective des hétérocycles de type : benzo[1,3]dioxoles, benzo[1,3]oxazoles et benzo[1,3]oxothiazoles. l’hydrocarboxylation du 4,4,4-perfluorobut-2-ynoate d’éthyle en utilisant des dérivés de l’acide 2-iodobenzoïque suivi d’une cyclisation intramoléculaire de manière ‟one-potˮ utilisant des sels de cuivres (II) nous a permis d’accéder régiosélectivement aux isocoumarines porteuses d’un groupement fluoroalkyle. Cette réaction a été étendue par la suite à la série hétéroaromatique faisant appel aux dérivés indoliques porteurs d’une fonction acide en positions 2 et d’un atome d’iode en position 3. Cette approche a permis de synthétiser de nouveaux hétérocycles fluorés à savoir des indolo[2,3-c]pyran-1ones. Nous avons exploité aussi une partie de potentiel offert par les structures énynoates synthétisées pour synthétiser des pyran-2H-ones originales porteuses d’un groupement fluoroalkyle par une stratégie d’iodolactonisation. Les réactions du couplage de type Sonogashira ont permis la synthèse d’une diversité d’alpha pyrones
Fluorinated heterocyclic compounds can be found among potent pharmaceuticals,crop protection agents, and products of technical importance. This mergingarea of organic, heterocyclic, and fluoroorganic chemistry is still rapidly growing andin the past decades a large number of fluorinated heterocyclic materials have been discovered. In this work, an efficient and original method was developed for the synthesis of 3,3-dialkoxy propionate bearing a perfluoroalkyl group in b-position from fluorinated alkyne and alcohols using base-catalyzed double Michael addition reaction. This method provides easy access to a-perfluoro ketals with reasonable to good yields with total regioselectivity. This procedure was extended to the phenol derivatives, and a fluorinated enol ether derivatives were selectively synthesized. The use of catechol and derivative allowed the synthesis of fluorinated heterocycles such as benzo[1,3]dioxoles, benzo[1,3]oxazoles and benzo[1,3]oxothiazoles. Copper-catalyzed annulation of aromatic and heteroaromatic b-iodo-a,b-unsaturated carboxylic acids with fluorinated alkyne 1 was developed. This strategy offers a simple and efficient route for the synthesis of isocoumarins and indolo[2,3-c]pyrane-1-ones. This family of compounds are known to have various biological properties; indolo[2,3-c]pyrane-1-one derivatives exhibit anti-cancer potential towards human cervix adenocarcinoma and antinociceptive and anti-inflammatory activity. Fluorinated pyrane-2H-ones bearing an iodine atom in position 5 have been also described. The a-pyrones constitute an important class of biologically active compounds
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Wang, Ya-Po, and 王雅柏. "Density Functional Theory Study of Base-Assisted Intramolecular Alkyne Hydroalkoxylation." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/77387944884792309771.

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Abstract:
碩士
高雄醫學大學
醫藥暨應用化學研究所
101
Oxygen-containing heterocycles are present in a wide range of bioactive products. Synthesis methods of such heterocycle are growing importance. The addition of O-H nucleophile to alkyne represents one of the great methods. In this thesis, density functional theory of M06-2X/6-31+G* theory level was employed to investigate the base-assisted intra-molecular alkyne hydroalkoxylation reaction. It is assumed that there are two possible pathways; the “alkyne path” in which the cyclization directly occurs via the nucleophilic addition of the hydroxyl group on the alkyne, and the “allene path” where the allene intermediate is formed prior to the cyclization. Four terminal substituents (including hydrogen, phenyl, anisole and trifluoromethyl benzene) have been calculated.Our calculations show that, in the absence of the K2CO3 the intramolecular cyclization reaction cannot take place. For all the four molecular systems under investigation, the allene pathway is more favorable.
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Book chapters on the topic "Hydroalkoxylation"

1

Teles, J. Henrique. "Hydration and Hydroalkoxylation of CC Multiple Bonds." In Modern Gold Catalyzed Synthesis, 201–35. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2012. http://dx.doi.org/10.1002/9783527646869.ch8.

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2

Julian, Lisa D. "Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Hydroamination or Hydroalkoxylation Reactions." In Topics in Heterocyclic Chemistry, 109–55. Berlin, Heidelberg: Springer Berlin Heidelberg, 2013. http://dx.doi.org/10.1007/7081_2013_105.

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3

"1.4.6 Hydrothiolation, Hydroalkoxylation, and Hydroaryloxylation." In N-Heterocyclic Carbenes in Catalytic Organic Synthesis 1, edited by Nolan and Cazin. Stuttgart: Georg Thieme Verlag, 2018. http://dx.doi.org/10.1055/sos-sd-223-00199.

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4

Hensen, K., C. Mahaim, and W. F. Hölderich. "Heterogeneously-catalyzed hydroalkoxylation of limonene and alpha-pinene in the presence of beta zeolite." In Studies in Surface Science and Catalysis, 1133–40. Elsevier, 1997. http://dx.doi.org/10.1016/s0167-2991(97)80749-5.

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