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Showing 1 to 20 of 103 for “"Suzuki-Miyaura"”.
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Studies In the Optimization of the Suzuki-Miyaura Reaction
… have been made to optimize the Pd-catalyzed Suzuki-Miyaura reaction, but there is to date no generally useful protocol and forcing conditions are often required. One reaction variable that has often been neglected is the extent to which the supposed catalysts, bisphosphinepalladium(0) …
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Synthesis of pinane thromboxane A₂ via suzuki-miyaura coupling
… on the synthesis of pinane thromboxane A₂ via a Suzuki-Miyaura coupling. Advantages of this route include the first example of the use of the Suzuki coupling with this compound, fewer steps within the synthesis and the use of less-toxic chemicals. Accomplishing the Suzuki-Miyaura coupling has …
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Suzuki-Miyaura mediated biphenyl synthesis: a spotlight on the boronate coupling partner
… a privileged scaffold. The palladium-catalysed Suzuki-Miyaura (SM) coupling is one of the most important and efficient strategies for the synthesis of symmetrical and unsymmetrical biaryl compounds; the arylboronic acid or ester is a key partner in this coupling reaction. This work presents the …
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Advances in Selectivity of the Suzuki-Miyaura and Hofmann-Löffler-Freytag Reactions
… are the investigations into new methods for the Suzuki-Miyaura and Hofmann-Löffler-Freytag reactions that proceed with predictable selectivity. </p><p>Tactical advances have resulted in the development of selective, serial, and exhaustive cross-coupling transformations of alkyl pinacol boronic …
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Pre-transmetalation intermediates in the Suzuki-Miyaura reaction revealed: the missing link
The Suzuki-Miyaura reaction is currently the most practiced cross-coupling reaction due to its broad applicability, low toxicity of the metal (B), and the wide variety of commercially available boronic acid substrates. Despite the popularity of the Suzuki-Miyaura reaction, the precise manner in …
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STEREOSPECIFIC SUZUKI-MIYAURA CROSS-COUPLING OF CHIRAL BENZYLIC BORONIC ESTERS AND VINYL BROMIDES
The Suzuki-Miyaura cross-coupling reaction is a powerful method for the construction of carbon-carbon bonds in academia and industry. Despite extensive research in this area and the significance of the reaction, it is most often employed to prepare flat, Csp2-Csp2 bonds between two aryl groups. …
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Vom Phenol zum Naturstoff : Entwicklung nachhaltiger Mikrowellen-vermittelter SUZUKI-MIYAURA-Kupplungen und Tandem-Reaktionen
… Aufbau von Biphenolen mittels Pd/C-katalysierten Suzuki-Miyaura-Kupplungen entwickelt. Diese Methoden sind insofern äußerst effizient, da der ansonsten gebräuchliche Syntheseweg über drei Reaktionsschritte somit auf lediglich eine Reaktionsstufe reduziert wurde. Weiterhin wurden die …
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One-Pot Synthesis of meta-Substituted Phenols via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling and Oxidation
We have developed a two-step synthesis of meta-substituted phenols in one pot, in good to excellent yield. A Pd2+ source is the catalyst for both steps of the synthesis, which includes a cross-coupling reaction between -chlorocyclohexenones with boronic acids, followed by aerobic oxidation of the …
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Ligand design principles for perfecting stereoretention in Suzuki-Miyaura cross-coupling of unactivated CSP3 boronic acids
The strategy of building block-based, iterative synthesis has revolutionized the preparation of oligonucleotides and oligopeptides. However, small molecules possess greater structural diversity than these classes of macromolecules. The development of an iterative, building block-based synthetic …
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Nickel-catalyzed Suzuki-Miyaura reactions of unactivated halides with alkyl boranes and planar-chiral borabenzene catalysts for Diels-Alder reactions
… an extension directing groups for the asymmetric Suzuki-Miyaura reactions halides. ... Part II details work towards an asymmetric Diels-Alder reaction between cyclopentadiene and methacrolein catalyzed by a planar-chiral boron Lewis acid. This system exhibits a level of turnover that is …
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I. Reaction mining—a next-generation platform for reaction discovery II. Rapid, anhydrous, homogenous Suzuki-Miyaura cross-coupling of aryl and alkylboronates
… preparative methods for aryl-aryl and B-alkyl Suzuki-Miyaura cross-coupling of boronic esters and boronates. Chapter 1 describes previous efforts by Sarlah and Shved to accelerate the reaction discovery process with the combination of data science, HTE, and artificial isotope distributions. A …
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Transmetalation from boronic esters to arylpalladium complexes without prior hydrolysis – mechanistic studies and preparative applications in the anhydrous, Suzuki-Miyaura cross-coupling reaction
… catalyzed, cross coupling reactions, the Suzuki-Miyaura reaction has emerged as the most popular method because of the relative non-toxicity of organoboron derivatives, the extensive reaction scope that has been demonstrated with the method, and the inertness of organoboron reagents …
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Expedient access to C-aryl linked saturated heterocyclic motifs
… systems. After initial investigation into a Suzuki-Miyaura approach towards the molecules of interest, the development of a one-pot Suzuki-Miyaura-hydrogenation was explored. This method was found to be highly general and tolerant of a wide range of functionalities. Scheme 1: Developed …
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ADVANCES IN THE DIRECTED ORTHO METALATION, SUZUKI-MIYAURA CROSS COUPLING, AND RING-OPENING REACTIONS OF INDAZOLES. SYNTHESIS OF LUMINESCENT ACRIDINE AND NOVEL INDAZOLE-BASED OXAZABORINES
The Directed ortho Metalation (DoM) reaction is a ubiquitous tool in the synthesis of polyfunctionalized aromatic and heteroaromatic molecules. Its regioselective nature endowed by the virtue of directed metalation groups (DMGs) coupled with its compatibility alongside many other well-established …
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Synthesis of α, β-Substituted Alkenylphosphonates from α-Phosphonovinyl Triflates: I) Palladium Catalyzed Suzuki-Miyaura Cross-coupling with Aryl Boronic Acids II) Palladium Catalyzed Reduction
… through an environmentally friendly Pd-mediated Suzuki reaction of α-phosphonovinyl triflates and aryl boronic acids. The cross-coupling reactions were completed using simple reaction conditions, green solvents (isopropyl alcohol/H<sub>2</sub>O), a heterogeneous catalyst with a very low mole …
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Prediction of higher selectivity catalysts by a computer driven workflow and machine learning and computational investigation of boronate esters in the Suzuki-Miyaura cross coupling
Chapter one of this work provides a comprehensive overview of chemoinformatics in enantioselective catalysis. Chapter two is comprised of completely unpublished work detailing the synthesis of a diverse set of bisoxazoline ligands in the planned optimization of an enantioselective aziridination …
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A novel route to fluoroarenes from trifluoroethanol
… to (iodo)difluoroenols which participated in Suzuki-Miyaura coupling with a range of aryl-boronic acids and potassium aryl-trifluoroborates. Side reactions of the Suzuki-Miyaura couplings were circumvented by using tertiary butanol as the reaction solvent. Low temperature preparation of …
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Structural studies on biaryl phosphines and palladium complexes composed of biaryl phosphines
… examples of traditionally difficult Suzuki-Miyaura reactions are presented along with a fluorescent sensor that can be used to monitor boronic acid consumption in Suzuki-Miyaura reactions in situ. Finally, a rationale behind the resistance of dialkylbiaryl phosphines toward oxidation …
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METAL-CATALYSED CROSS-COUPLING REACTIONS OF NITROGEN HETEROCYCLES
… with aryl or heteroarylboronic acids under Suzuki-Miyaura conditions to provide a rapid entry to tris(hetero)aryl scaffolds comprising two or three N-heterocyclic rings. The sequential N-C and C-C couplings can be performed in a one-pot process. 1,5-Di(hetero)arylated-pyridin-2(1H)-one …
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