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Showing 1 to 20 of 21 for “"Hypervalent iodine"”.
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Hypervalent iodine reagents for protein functionalisation
… converted to diazo-sulfonium derivatives using hypervalent iodonium salts, producing versatile conjugates that can undergo further bioorthogonal modifications. This powerful strategy proceeds with high efficiency and chemoselectivity across a range of small proteins and polypeptides. In this …
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INVESTIGATIONS OF HYPERVALENT IODINE COMPOUNDS IN ORGANIC TRANSFORMATIONS
… for various organic transformations with hypervalent iodine compounds, which have attracted explosive interest among chemistry communities because of their versatility and mildness in inducing many organic transformations. Chapter 1 briefly introduces the history of hypervalent iodine …
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HYPERVALENT IODINE METHODS FOR CARBON–NITROGEN AND CARBON–CARBON BOND FORMATION
… more practical and sustainable fashion by using hypervalent iodine reagents. In this dissertation we demonstrate the synthetic applications of λ3-iodane reagents towards the formation of challenging carbon-carbon and carbon-nitrogen bonds in a complementary way to the methods already reported. …
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HYPERVALENT IODINE-MEDIATED HETEROCYCLIC GROUP TRANSFER REACTIONS TO OXIDATIVE OLEFIN DIFUNCTIONALIZATION
… Both methods are promoted by nitrogen-ligated hypervalent iodine reagents (N-HVIs). These novel class of reagents serve as “heterocyclic group transfer reagents,” incorporating diverse pyridinium salts under mild conditions and in excellent yields. Heterocyclic Group Transfer reactions have …
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Preparation, structural studies and chemical properties of new hypervalent iodine compounds
… on preparation of a new class of heterocyclic hypervalent iodine (III) compounds, the benziodoxaboroles, and a series of heterocyclic compounds containing trivalent iodine, oxygen, and boron in a five-membered ring were prepared and structurally investigated by X-ray crystallography. Second …
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Applications of Hypervalent Iodine Reagents: From Enantioselective Copper-Catalysed Arylation-Semipinacol Cascade to Methionine Functionalisation for Peptide Macrocyclisation
The unifying theme of this thesis is the exploitation of the reactivity of aryliodonium salts as electrophile transfer reagents. In the first part of the thesis, diaryliodonium salts are employed as arylation reagents for the enantioselective copper-catalysed arylative semipinacol rearrangement …
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I. Biomimetic oxidations using non-heme iron catalysis. II. Palladium- and hypervalent iodine-catalyzed tandem wacker-dehydrogenation of terminal olefins
… test biosynthetic proposals. II. PALLADIUM AND HYPERVALENT IODINE-CATALYZED TANDEM WACKER- DEHYDROGENATION OF TERMINAL OLEFINS Catalytic C—H functionalization reactions promise to increase synthetic efficiency by enabling the direct installation of useful functionality onto traditionally …
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Selective Protein Functionalisation at Methionine
… of a novel bioconjugation method employing hypervalent iodine reagents for the selective functionalisation of methionine residues. The broad scope and excellent biocompatibility of the reaction is demonstrated, with a number of different polypeptide and protein substrates tolerated. …
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Development of new catalytic transformations and reagents for the construction of C-N and C-S bonds
… 3. Structural Reevaluation of the Electrophilic Hypervalent Iodine Reagent for Trifluoromethylthiolation. Hypervalent iodine [lambda]3-benziodoxoles are common electrophilic transfer reagents known for their enhanced stability compared to their non-cyclic analogues. Here we present data showing …
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I. Sulfonium-Mediated Oxidative Glycosylation of Glycal Donors for the Synthesis of C(2)-Hydroxy-Beta-Glycosides. II. Hypervalent Iodine (iii)-Mediated Oxidative Glycosylation of Glycal Donors for the Synthesis of C(2)-Acyloxy-Beta-Glycosides. III. Efforts Toward the Synthesis of Immunologic Adjuvant Qs-21a(api)
Development of two novel glycosylation procedures, and the synthesis of immunologic adjuvant QS-21Aapi is reported. In the first glycosylation procedure, glycals were employed as glycosyl donors and activated with a reagent combination of diphenyl sulfoxide and triflic anhydride. This …
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Synthesis and Molecular Pharmacology of the Diazonamides
… The central feature of our approach employed a hypervalent iodine species to oxidatively install the central diazonamide diarylaminal. This net two electron oxidative internal crosslink between tyrosine and tryptophan accesses the diazonamide core from a simple peptide-derived substrate. …
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Metal-free syn-dihydroxylation of alkenes using malonoyl peroxides
… syn-1,2- dioxygenation of alkenes. The use of hypervalent iodine, selenium, sulfur and peroxide reagents are discussed in terms of the advantages and limitations of each method. Chapter 2 details a mechanistic investigation into the dihydroxylation reaction using cyclopropyl malonoyl peroxide …
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Synthesis of N-Heterocycles and Thiocines via Electrophilic Divalent Reactive Intermediates
… formation to yield dibenzazepines. The use of hypervalent iodine reagents motivated me to examine the possibility of using the same reactivity to achieve sp3-C–NAr bond formation. An iodine(III)-catalyzed process was developed using 0.5 mol % of iodobenzene, 2.3 equivalents of Selectfluor, and …
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Total Synthesis of Lasionectrin and Synthetic Studies Towards Pestaloxazine A
… the fused bicycle in a single step using chiral hypervalent iodine was ultimately unsuccessful. Our revised synthetic route to lasionectrin (13) involved late-stage installation of the fused pyrone-tetrahydrofuran ring system via tandem dihydroxylation-tosylate displacement beginning from alkene …
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Investigations of Catalysts Which Utilise Non-Covalent Interactions to Control Enantioselectivity in Rhodium-Catalysed Amination of C(sp3)–H Bonds
… to be viable. Additionally, the key role of a hypervalent iodine additive was uncovered. Overall, this thesis seeks to expand the utility of ion-paired chiral cations for enantioselective C–H functionalisations, an under-developed strategy within asymmetric catalysis.
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Palladium-mediated C–H Functionalization of Aliphatic Amines via High Valent Palladium(IV) Intermediates
… a diverse range of functionalized products. Hypervalent iodine(III) reagents were initially investigated as oxidants in the development of a Pd-catalyzed intramolecular γ C–H amination process to form azetidine products from hindered cyclic amines. Following this, aryl halides containing …
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Meeting the challenges: carbon-hydrogen bond activation and cancer treatment
… by dioxygen. The reaction between the hypervalent iodine regents PhI(OAc)2 and PhI(OTFA)2 and the bis-NHCPd( II)-Me2 complex gave only reductive elimination products. Therefore, this system can act as a model system, which is able to providing valuable information of the product forming …
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Developments in Nickel-catalyzed Transfer Hydrocyanation Reactions and Novel Skeletal Editing Strategies through Nitrogen Atom Insertion
… generated by mixing commercially available hypervalent iodine(III) reagents and ammonia sources. In an initial reaction development study, the use of TBS-protected indoles enabled the efficient conversion to the corresponding quinazoline or quinoxaline heterocycles depending on the …
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SYNTHESES AND ESTROGENICITY STUDY OF DIETHYLSTILBESTROL AND BISPHENOL-A ANALOGS AS POTENTIAL REPLACEMENT FOR BISPHENOL-A AND INVESTIGATION ON NOVEL REACTIONS INDUCED BY IODANE/QUATERNARY AMMONIUM HALIDES
Dynamic isomerization of diethylstilbestrol (DES) makes it difficult to ascertain the active estrogen between its E and Z isomers. An indirect approach has been used in this project to identify the active estrogen. Methoxylated E- and Z-DES (13 and 14) and 9,10-diethylphenanthrene-3,6-diol (15), a …
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Towards the Development, Application and Understanding of Copper-Catalysed Alkene Functionalisation Processes Using Iodonium Salts
This thesis comprises three projects focused on the use of the combination of catalytic copper and iodonium salts towards the functionalisation of alkenes. Chapter 2 details the development of an enantioselective and regiodivergent allylic amide arylation procedure using a specific …
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