Дисертації з теми "Borylation reaction"
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Palau, Lluch Gerard. "alpha,beta-difunctionalization of alpha,beta-unsaturated carbonyl compounds through borylation reaction." Doctoral thesis, Universitat Rovira i Virgili, 2015. http://hdl.handle.net/10803/311620.
Повний текст джерелаEsta tesis presenta los resultados pertenecientes a nuevas metodologias aplicadas hacia la obtención de productos alfa-funcionalizados y beta-borilados que no tienen precedente en la bibliografia, a partir de cetonas alfa,beta-insaturadas. Las funcionalizaciones estudiadas han sido utilizando fluor, para obtener alfa-fluoro beta-boryl cetonas; halogenos, para obtener alfa-halo beta-boril cetonas (siendo los halogenos cloro y bromo); y finalmente la difuncionalización de cetonas alfa,beta-insaturadas para obtener alfa-aryl beta-boryl cetonas, que tal y como se presenta en la tesis, han sido los productos intermedios hacia la sintesi de 2-aryl-1,3-dionas, que són productos de sintesis muy valorados en la indústria por sus propiedades como pesticidas. En todos los tres casos, se consiguió la obtención de los productos difuncionalizados, de los cuales ninguno habia sido previamente presentado en la bibliografia existente, concluyendo que éste ha sido un trabajo pionero hacia la sintesi y obtención de estos compuestos difuncionalizados.
This thesis presents the results concerning new methodologies towards the obtantion of alpha-functionalized beta-borylated compounds from alpha,beta-unsaturated carbonyl compounds, with no precedent in the litherature. The functionalizations studied focused on fluorine, to obtain alpha-fluoro beta-boryl ketones; halogens, to obtain alpha-halo beta-boryl ketones (being the halogens chlorine and bromine); and finally, the difunctionalization of alpha,beta-unsaturated ketones to obtain the corresponding alpha-aryl beta-boryl ketones, which as presented in this thesis, they have been the intermadiates towards the synthesis of 2-aryl-1,3-diones. 2-aryl-1,3-diones are highly valued products in industry for their properties as pesticides. In the three cases studied, we obtained the desired difunctionalized products, which any of them has been previously presented in the existing literature, concluding that this has been a pioneering work towards the synthesis and obtantion of such difunctionalized compounds.
Eliseeva, Maria N. "New Route to a [5,5] Carbon Nanotube End-Cap via Direct Borylation of Corannulene." Thesis, Boston College, 2011. http://hdl.handle.net/2345/2752.
Повний текст джерелаThe Scott lab is interested in the functionalization of corannulene as a building block for large polycyclic aromatic hydrocarbons and carbon nanotube end-cap precursors. Toward that end, a new approach to the direct five-fold borylation of corannulene with iridium (I) catalysts via C-H activation has been explored. It has been discovered that the addition of catalytic amounts of base to the reaction mixture promotes the formation of symmetrical penta-borylated corannulene in a good yield on a sizable scale. All byproducts can be easily removed with iterative methanol washes. The present work also provides proof of the reversibility of the direct borylation reaction under the conditions used. Furthermore, modified Suzuki-Miyaura conditions have been employed to synthesize pentakis(2,6-dichlorophenyl)corannulene, a precursor for a [5,5] carbon nanotube end-cap. The reported reactions provide good yields and are scalable
Thesis (MS) — Boston College, 2011
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
Sasaki, Ikuo. "Development of Novel Synthetic Methods of Organosilicon Compounds Utilizing Silicon-Containing Reactive Intermediates." Kyoto University, 2020. http://hdl.handle.net/2433/253508.
Повний текст джерелаGallanti, M. "STEREOSELECTIVE SYNTHESIS OF A-AMINO ACIDS B-SUBSTITUTED WITH A 4,5-DIHYDROISOXAZOLE NUCLEUS AND OF TERTIARY AND QUATERNARY ALLYLSILANES." Doctoral thesis, Università degli Studi di Milano, 2012. http://hdl.handle.net/2434/168366.
Повний текст джерелаLarsson, Johanna M. "Transition metal-catalyzed allylic and vinylic functionalization : Method development and mechanistic investigations." Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2013. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-89524.
Повний текст джерелаAt the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 4: Manuscript.
Yu, Zhiyong. "Total Synthesis of (+)-Discodermolide by Catalytic Stereoselective Borylation Reactions." Thesis, Boston College, 2014. http://hdl.handle.net/2345/bc-ir:103737.
Повний текст джерела(+)-Discodermolide is a marine natural product and is one of the most potent microtubule stabilizers in human cell lines. Because of its unique linear structure and important properties, a number of total syntheses of (+)-discodermolide and its derivatives have been reported. Herein, an efficient, highly convergent, and stereocontrolled total synthesis is presented (Chapter 2). The synthesis relied on the development of three catalytic and stereoselective processes: platinum-catalyzed asymmetric diene diboration, nickel-catalyzed diastereoselective hydroboration of chiral dienes (Chapter 1), and nickel-catalyzed borylative diene-aldehyde coupling (see Chapter 4). Combination of these reactions allows preparation of the target in a short sequence. Moreover, the development of rhodium-catalyzed asymmetric hydroformylation (Chapter 3) makes this approach the first Roche ester free (+)-discodermolide synthesis
Thesis (PhD) — Boston College, 2014
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
Xu, Conghui. "Rhodium-mediated Activation and Borylation Reactions of Fluorinated Olefins." Doctoral thesis, Humboldt-Universität zu Berlin, 2020. http://dx.doi.org/10.18452/22174.
Повний текст джерелаThe dissertation reports on studies on the reactivity of rhodium complexes towards different fluorinated olefins with a focus on C–F activation steps and borylation reactions. The rhodium(I) hydrido complex [Rh(H)(PEt3)3] (1) was employed as catalyst in the reactions of HFO-1234yf, HFO-1234ze, HFO-1225zc and HFO-1225ye with HBpin. A product mixture consisting of borylation products was obtained. Selective mono and dihydroboration reactions of 3,3,3-trifluoropropyne were achieved by employing complex 1 as the catalyst. Similarly, trifluoroethylene was also converted into a mixture of products by the reaction with HBpin with complex 1 as the catalyst. A stoichiometric reaction of complex 1 resulted in the C–F bond activation as well as a coordination of trifluoroethylene to give complex trans-[Rh(F)(ƞ2-CF2CFH)(PEt3)2]. Furthermore, the C–F bond activation was also realized with complex 1 and 1,1,2-trifluorobutene. Mechanistic investigations of the reaction of complex 1 towards 1,1,2-trifluorobutene at variable temperatures indicated the formation of products of coordination, insertion of the olefin and subsequent β-H elimination, C–F oxidative addition as well as HF reductive elimination steps. Furthermore, when utilizing complex 1 or [Rh(Bpin)(PEt3)3] (3) as catalysts, stoichiometric and catalytic hydroboration reactions of pentafluorostyrene occurred with HBpin. The rhodium(I) complexes 1 and 3 were capable of the coordination of the olefin and a C–F bond activation reaction with pentafluorostyrene, while complex [Rh(Me)(PEt3)3] promoted the C–H bond activation. At 333 K, the activation of the fluorinated aromatic ring occurred at the 4-position, while at room temperature, an activation at the 2-position was preferred.
Audi, Hassib. "Synthèse stéréosélective d'aminoacides boronatés et silylés pour le piégeage de fluorures, à visée imagerie médicale." Thesis, Dijon, 2012. http://www.theses.fr/2012DIJOS094.
Повний текст джерелаThe stereoselective synthesis of new boronato amino acid derivatives, using Wittig and C-H iridium-catalyzed borylation as key step reactions, is described. Firstly, the synthesis of amino ester precursors bearing an aromatic moiety in -position of the lateral chain, was achieved by Wittig reaction of a phosphonium salt derived from amino acid with the corresponding aromatic aldehyde, then esterification and hydrogenation. The reaction of the amino esters with the bis(pinacolato)diborane reagent (B2Pin2) in presence of an iridium complex as catalyst, leads to the corresponding boronato derivatives in yields up to 74 %. Finally, the iodo- or trifluoroborato derivatives were easily prepared from the boronato amino acid by reaction either with NaI or with KHF2. The hydrolysis of the trifluoroborato amino acid derivatives was studied in buffer solution using 19F NMR monitoring. In the case of the difluorophenyl and thiophenyl amino esters, the corresponding trifluoroborates derivatives show good to excellent stability toward hydrolysis. In addition, the stereoselective synthesis of silano amino acid has been developped by Wittig reaction of the phosphonium salt derived from amino acid with the 4-di-t-butylsilanobenzaldehyde. The silano amino acid was used to prepare a dipeptide with 80% yield, and the corresponding fluorosilane derivative without racemization, by reaction with KF. The hydrolysis of the fluorosilylated dipeptide in aqueous media shows an excellent stability, up to 10 days. Finally, this stereoselective synthesis of hetero substituted amino acids, offers a promising tool for the application of the boronated and silyled derivatives to the fluoride labeling
Coapes, Richard Benjamin. "Rhodium catalysed borylation reactions via direct and indirect C-H activation." Thesis, Durham University, 2002. http://etheses.dur.ac.uk/4176/.
Повний текст джерелаXu, Conghui [Verfasser]. "Rhodium-mediated Activation and Borylation Reactions of Fluorinated Olefins / Conghui Xu." Berlin : Humboldt-Universität zu Berlin, 2020. http://d-nb.info/1222973480/34.
Повний текст джерелаDang, Li. "Density functional theory studies of copper(I) mediated borylation and carboxylation reactions /." View abstract or full-text, 2010. http://library.ust.hk/cgi/db/thesis.pl?CHEM%202010%20DANG.
Повний текст джерелаYang, Lichen. "Studies on Site-Selective C-H Borylation Reactions of Arenes and Heteroarenes." Kyoto University, 2020. http://hdl.handle.net/2433/253291.
Повний текст джерелаSolana, González Jorge. "Copper and iridium conjugate addition : cyclisation processes, domino reactions." Thesis, University of Edinburgh, 2015. http://hdl.handle.net/1842/10471.
Повний текст джерелаXiao, Lu. "Copper-Catalyzed Borylation of Hemiaminal Ethers and Ruthenium-Catalyzed Tandem Reactions of Nitrogen-Tethered Dienes." Thesis, Boston College, 2016. http://hdl.handle.net/2345/bc-ir:107234.
Повний текст джерелаChapter 1 Bisphosphine monoxides have unique coordinating capabilities with transition metals. Several research groups have independently reported transition metal-catalyzed highly stereoselective reactions by using chiral bisphosphine monoxides as the ligands. A review of recent works in this field is provided in this chapter to showcase the features of this class of ligand. Chapter 2 We have developed a copper-catalyzed borylation method to synthesize α-aminoboronic esters, which are biologically interesting molecules in enzyme inhibitions. Employment of hemiaminal ethers as substrates to in situ generate the corresponding aldimines obviated purification of the unstable aldimines and potential imine-enamine tautomerization. By using a chiral bisphosphine monoxide ligand in our copper-catalyzed borylation conditions, we successfully synthesized a variety of enantioenriched alkyl-substituted α-aminoboronic esters in good yields and with good enantioselectivity. Chapter 3 A ruthenium-catalyzed three-step tandem sequence was established to prepare nitrogen-protected 2,3-dihydroxypyrrolidines and 2,3-dihydroxypiperidines. This tandem sequence includes ring-closing metathesis, olefin isomerization and olefin dihydroxylation, and utilizes the second-generation Grubbs’ catalyst as the initial ruthenium precatalyst. Readily accessible nitrogen-tethered dienes were used as the substrates to prepare the heterocyclic compounds in an efficient fashion. Through optimization, we discovered the optimal conditions for ruthenium-catalyzed dihydroxylation of ene-carbamates and ene-sulfonamides, which were the challenging substrates in the previous methods
Thesis (PhD) — Boston College, 2016
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
French, Rosalind M. "Asymmetric Lithiation/borylation reactions of secondary Benzylic carbamates in the synthesis of tertiary alcohols." Thesis, University of Bristol, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.528073.
Повний текст джерелаEichhorn, Antonius [Verfasser], and Todd B. [Gutachter] Marder. "Copper(I) catalyzed borylation and cross-coupling reactions / Antonius Eichhorn ; Gutachter: Todd B. Marder." Würzburg : Universität Würzburg, 2018. http://d-nb.info/1166054896/34.
Повний текст джерелаMorimoto, Masao. "Development of Highly Efficient Synthetic Reactions Catalyzed by Transition Metals." 京都大学 (Kyoto University), 2014. http://hdl.handle.net/2433/188615.
Повний текст джерелаKremnev, Jimmy D. "Visible light mediated borylation and [2+2] cycloaddition reactions of Thiazolino Ring Fused 2-Pyridones." Thesis, Umeå universitet, Kemiska institutionen, 2020. http://urn.kb.se/resolve?urn=urn:nbn:se:umu:diva-177966.
Повний текст джерелаKitano, Masaaki. "Chemistry of meso-Free Subporphyrins." 京都大学 (Kyoto University), 2016. http://hdl.handle.net/2433/215329.
Повний текст джерелаYamamoto, Yutaro. "Studies on Palladium-Catalyzed Reactions of Aryl Chlorides with Lewis Acidic Boron or Organosilicon Reagents." 京都大学 (Kyoto University), 2017. http://hdl.handle.net/2433/225430.
Повний текст джерелаCho, Hee Yeon. "Catalytic Borylative Multicomponent Coupling Reactions and Novel Chemistry of Polycyclic Aromatic Hydrocarbons." Thesis, Boston College, 2013. http://hdl.handle.net/2345/3398.
Повний текст джерелаThesis advisor: James P. Morken
Expeditious establishment of molecular complexity in a stereoselective manner is a prominent goal in organic synthesis. In this regard, multicomponent coupling reactions have received substantial attention due to their ability to access complex molecules from simple starting materials in a single step. Chapter 1 is a comprehensive review on catalytic bismetallative multicomponent reactions. The scope of this process in terms of both bismetallic reagents and the pi components are broad enough to be generally applied to more elaborate synthetic sequences. Particularly, contemporary applications of the bismetallative multicomponent coupling reactions, in which high enantio- and/or diastereoselectivities are displayed, have enabled the study of this area to make a significant step forward. Chapter 2 presents nickel-catalyzed coupling reactions of aldehyde, diene, and a diboron reagent in the presence of a trialkyl phosphine ligand. Compared to borylation reactions with one pi-component, these borylative multicomponent reactions (involving two pi components) lead to formation of a new C-C bond between the pi components as well as generation of highly functionalized, stereodefined products. Chapter 3 describes a remarkable turnover in regioselectivity of the borylative multicomponent coupling when PCy3 is replaced with P(SiMe3)3. In particular, the products from the reactions with P(SiMe3)3 feature three contiguous stereocenters and an alpha-chiral allylboronate. The effect of P(SiMe3)3 ligand on the product selectivity is intriguing. According to the experimental and computational results, it has an ability to act as an electron acceptor, which will facilitate reductive elimination from the intermediate nickel complex during the course of the reaction. In Chapter 4, we show that borylative ketone-diene coupling reactions can be accomplished in high yields and with excellent levels of diastereocontrol. This reaction occurs in a predictable fashion, yet with regioselection that is distinct from related aldehyde-diene coupling reactions. The reaction products from these coupling processes, which possess tertiary alcohol functionality and an allylic alcohol moiety, are particularly well suited for the preparation of polyketide natural products. Chapter 5 presents investigations on bowl-shaped geodesic polyarenes, which are the missing links between the "classic" planar polycyclic aromatic hydrocarbons (PAHs) and the spheroidal fullerenes. The present study has shown that open geodesic polyarenes can feature chemistry inherent to both classes of aromatics. The curved pi system induces unequal environments on the two faces of circumtrindene, significant strain energy to the molecule, and non-identical bond lengths. Along with the electronic effects, the stereoelectronic effect enabled the site-selective functionalization with fullerene-type chemistry. On the other hand, the edge carbons, which are not present in fullerenes, still possess reactivity of common planar PAHs. Chapter 6 describes the intermolecular oxidative cyclotrimerization reactions of alkenes and aromatic compounds with DDQ and trifluoromethanesulfonic acid. The Scholl-type oxidation reactions involving alkenes have never been demonstrated. Moreover, the DDQ/acid system has never been used for the intermolecular oxidative cyclization reactions. This convenient non-metallic reagent system (DDQ/TfOH) is advantageous over the metal-based Scholl-type oxidants because it eliminates the possibility of halogenation of aromatic compounds and the reduced oxidant can be reoxidized. In Chapter 7, the regioselective formation of cyclic trimers from substituted benzenes and heteroaromatic compounds is demonstrated. This DDQ/TfOH method provides a simple and convenient synthetic route toward star-shaped oligomers containing triphenylene or isotruxene cores. Furthermore, the experimental outcome suggests that this oxidative process proceeds by an electron transfer mechanism. This is the first experimental evidence for mechanistic details on the Scholl-type oxidation
Thesis (PhD) — Boston College, 2013
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
Eck, Martin [Verfasser], Todd B. [Gutachter] Marder, Udo [Gutachter] Radius, and Matthias [Gutachter] Lehmann. "Iron- and Copper-catalyzed Borylation of Alkyl and Aryl Halides and B–B Bond Activation and NHC Ring-expansion Reactions of the Diboron(4) Compound Bis(ethylene glycolato)diboron (B\(_2\)eg\(_2\)) / Martin Eck ; Gutachter: Todd B. Marder, Udo Radius, Matthias Lehmann." Würzburg : Universität Würzburg, 2018. http://d-nb.info/1160876975/34.
Повний текст джерелаChou, Chun-Chin, and 周俊欽. "Borylation and Suzuki Reaction Catalyzed by NS-MCM-41-Pd and its One-Pot Application." Thesis, 2007. http://ndltd.ncl.edu.tw/handle/9gqx7d.
Повний текст джерела國立臺北科技大學
有機高分子研究所
95
ABSTRACT Title:Borylation and Suzuki coupling catalyzed by NS-MCM-41-Pd and its One-pot application Pages:89 School:National Taipei University of Technology Department:Institute of Organic and Polymeric Materials Time:July, 2007 Degree:Master Researcher:Chun-Chin Chou Advisor:Fu-Yu Tsai Keywords:suzuki coupling, mesoporous material, palladium complex The use of transition metal as a catalyst plays an important role in organic synthesis in modern industry. Generally, homogeneous catalysts could get better yields under mild conditions, but difficult to be separated from the reaction mixtures after reaction finishing and the residue of the catalyst may destroy the purity and characteristics of the products. On the other hand, heterogeneous catalysts could be easily recovered by simple separation after reaction done and reuse for the next reaction. Herein, we utilized nanosized mesoporous silica materials, NS-MCM-41 (nano-sized MCM-41), as an inorganic solid support and grafting the bipyridyl palladium complex onto the wall to be a heterogeneous catalyst. The physical properties of this material is steady and the worm-hole like structure of the channels enables reactants, salts and products could easily through-out the channels without blockade. Since there is large surface area (around 588 m2/g) inside the channels and the surface has a plenty of silanol group, we can modify complex include catalyst onto NS-MCM-41 by physic adsorption or chemical bonding. This thesis reports that the employment of NS-MCM-41-Pd in the formation of arylboronates and then these products are used as reactants for Suzuki coupling for its one-pot application. The content is composed of two parts: in the first part, we use NS-MCM-41-Pd as a catalyst that is applied on the borylation of aryl halides and pinacolborane; and in the second part, NS-MCM-41-Pd system is employed for Suzuki coupling of aryl halides and arylboronates. Finally, we directly try to proceed one-pot borylation/Suzuki coupling (BSC) reaction. The detail of the activities, recycled properties and leach out studies of NS-MCM-41-Pd for these reactions are discussed in this thesis.
Verma, Piyush Kumar. "Cobalt-nhc Complexes and Diazabutadienes in Activation of Mono/Diboron Compounds and Their Application in C-b Coupling Reactions." Thesis, 2021. https://etd.iisc.ac.in/handle/2005/5241.
Повний текст джерелаEichhorn, Antonius. "Copper(I) catalyzed borylation and cross-coupling reactions." Doctoral thesis, 2018. https://nbn-resolving.org/urn:nbn:de:bvb:20-opus-167332.
Повний текст джерелаDie dargelegte Arbeit gliedert sich in zwei Teile. In einem ersten wird die Synthese sowie stöchiometrische Modell-Reaktionen von definierten NHC-stabilisierten Kupfer(I)-Komplexen (NHC = N-heterocyclisches Carben) untersucht, um Einblick in das grundlegende Reaktionsverhalten in Borylierungs- und Kreuzkupplungsreaktionen zu erlangen. Der zweite Teil adressiert die Reaktivität der eingesetzten Liganden (NHCs und CaaCs = cyclische Alkyl Amino Carbene) gegenüber verwendeten sowie möglichen Substraten (Arylboronsäureester und Diboran(4)-Verbindungen)
Eck, Martin. "Iron- and Copper-catalyzed Borylation of Alkyl and Aryl Halides and B–B Bond Activation and NHC Ring-expansion Reactions of the Diboron(4) Compound Bis(ethylene glycolato)diboron (B\(_2\)eg\(_2\))." Doctoral thesis, 2018. https://nbn-resolving.org/urn:nbn:de:bvb:20-opus-149791.
Повний текст джерелаIm ersten Teil der vorliegenden Arbeit wurde das Potential eisenkatalysierter Borylierungsreaktionen von Alkylhalogeniden (Substrate) mit B2pin2 als Borylierungsreagenz untersucht. Weiterhin wurden detaillierte und intensive Untersuchungen zur literaturbekannten kupferkatalysierten Borylierung von Arylhalogeniden durchgeführt, einschließlich eines Screenings von unterschiedlich funktionalisierten Substraten und diversen Alkoxybasen. Es wurde ebenfalls ein sehr umfangreiches Ligandenscreening durchgeführt. Des Weiteren wurden die mögliche Entstehung und der mögliche Einfluss von Kupfernanopartikeln auf die Borylierungsreaktion untersucht. Um Intermediate der kupferkatalysierten Borylierung zu untersuchen wurden Kupferphosphankomplexe als Vorläufermoleküle für die Synthese von Kupferborylkomplexen hergestellt. Aufgrund der sehr hohen Reaktivität gelang es jedoch nicht, die entsprechenden Kupferborylkomplexe zu isolieren und zu charakterisieren. Es gelang allerdings in einem in situ 11B{1H}-NMR-Experiment, ein 11B{1H}-Signal zu detektieren, welches in dem zu erwartendem Bereich für einen Kupferborylkomplex lag und einen ersten Hinweis für die Bildung eines solchen Kupferborylkomplexes lieferte. Im zweiten Teil der vorliegenden Arbeit wurde das alternative, lewissaure Diboran(4)-Derivat Bis(ethylenglykol)diboran (B2eg2) synthetisiert, um dessen Reaktivität mit der Reaktivität von anderen Diboran(4)-Verbindungen (z.B. B2neop2, B2cat2, B2pin2 und B2(NMe2)4) zu vergleichen. Hierfür wurden Reaktionen von B2eg2 mit unterschiedlichen Lewisbasen wie NHCs und Phosphanliganden durchgeführt und die mögliche Bildung von sp2-sp3 oder sp3-sp3 hybridisierten mono- bzw. bis-Addukten sowie mögliche NHC-Ringerweiterungsreaktionen untersucht. Im Allgemeinen wurde im zweiten Teil der Arbeit versucht ein besseres Verständnis über die Reaktivität von Diboran(4)-Verbindungen mit Lewisbasen zu erlangen, da beide als Reaktanten in übergangsmetallkatalysierten und metallfreien Borylierungsreaktionen verwendet werden. Dies macht es zwingend erforderlich die B–B-Bindungsaktivierung durch Lewisbasen zu verstehen, da hierdurch eine komplett neue Perspektive auf mögliche Reaktionspfade vieler Borylierungsreaktionen eröffnet wird
(10730742), Henry J. Hamann. "Amine-Boranes: Synthesis and Applications." Thesis, 2021.
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