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1
Corakci, Bengisu. "Substituted Quinoxaline And Benzimidazole Containing Monomers As Long Wavelength Photosensitizers For Diaryliodonium Salt Initiators In Photopolymerization." Master's thesis, METU, 2013. http://etd.lib.metu.edu.tr/upload/12615458/index.pdf.
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In this studyferrocenyl and naphthalenyl substituted quinoxaline derivatives
5,8- bis (2,3- dihydrothieno [3,4-b] [1,4] dioxin-5-yl)-2- (naphthalen-2-yl)- 3- ferrocenyl- 4a,8a-dihydroquinoxaline
5,8- bis (2,3-dihydrothieno [3,4-b] [1,4]dioxin-5-yl) -2- (phenyl) -3-ferrocenylquinoxaline
5,8-bis (2,3-dihydrothieno [3,4-b] [1,4]dioxin-5-yl) -2,3- di(naphthalen-2-yl)quinoxaline and trihexylthiophene and thiophene coupled benzimidazole derivatives
4-(tert-butyl)-4,7-bis(4-hexylthiophen-2-yl)spiro[benzo[d]imidazole-2,1-cyclohexane] and 4-(tert-butyl)-4, 7-bis(thiophenyl)spiro[benzo[d]imidazole-2,1-cyclohexane] were used as photosensitizers to broaden the active area of diaryliodonium salts. Both quinoxaline and benzimidazole derivatives are expected to be efficient in cationic photopolymerization with a variety of vinyl and oxide monomers at room temperature upon long wavelength UV irradiation. Photopolymerization will be initiated by diphenyliodonium salts and monitored with Optical Pyrometry. Characterization will be completed with optical absorption, flourescence studies and photopolymerization under solar irradiation.
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Peacock, Martin James. "The electrosynthesis of diaryliodonium salts." Thesis, University of Southampton, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.326302.
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Marchal, Lucas. "Synthèse de nouveaux candidats médicamenteux présentant une chiralité axiale C-N par le développement de nouveaux couplages C-N atroposélectifs." Electronic Thesis or Diss., Strasbourg, 2024. http://www.theses.fr/2024STRAF029.
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Les composés à chiralité axiale C–N ont démontré un potentiel significatif dans divers domaines, en particulier dans l'industrie pharmaceutique. Cependant, il existe actuellement peu de méthodologies connues permettant d’accéder à ces composés, et elles sont généralement limitées à des structures moléculaires très spécifiques. Afin de préparer de nouveaux atropisomères C–N d'intérêt, des méthodologies synthétiques innovantes doivent être développées. À cette fin, nous avons concentré nos efforts sur l'utilisation de sels de diaryliodonium comme partenaires de couplage hautement réactifs, ce qui nous a permis de concevoir un nouveau couplage C–N atropo-énantiosélectif catalysé au cuivre pour obtenir des benzoxazolones N-arylées énantio-enrichies. Les applications potentielles bioactives de ces molécules ont été étudiées et des études mécanistiques ont été menées pour concevoir un cycle catalytique pour ce couplage. De telles investigations approfondies ont été possibles grâce à une collaboration interdisciplinaire fructueuse. Le développement de nouvelles méthodologies a été étendu au premier couplage C–N atropo-énantiosélectif photoinduitC–N axially chiral compounds have demonstrated significant potential across various fields, especially in the pharmaceutical industry. However, there are currently only few known methodologies to access these compounds, which are generally restricted to very specific molecular scaffolds. In order to prepare new C–N atropisomers of interest, innovative synthetic methodologies must be develop. To this purpose, we focused our efforts of the use of diaryliodonium salts as highly reactive coupling partners which allowed us to design a new copper-catalyzed atropo-enantioselective C–N coupling to afford enantio-enriched N-aryl benzoxazolones. The potential bioactive applications of such molecules has been studied and mechanistic studies were carried out to design a catalytic cycle for coupling. Such in-depth investigations were possible thanks to a fruitful interdisciplinary collaboration. The development of new methodologies was further extended through the first photoinduced atropo-enantioselective C–N coupling
4
Bielawski, Marcin. "Efficient and High-Yielding Routes to Diaryliodonium Salts." Licentiate thesis, Stockholm : Department of Organic Chemistry, Stockholm University, 2008. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-7969.
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Lindstedt, Erik. "Metal-Free O- and C-Arylation with Diaryliodonium Salts." Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2017. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-140944.
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This thesis concerns the development of metal-free applications using diaryliodonium salts. The first project describes an arylation protocol of allylic and benzylic alcohols in aqueous media. The method proceeds under mild conditions and the ether products were obtained in moderate to good yields. The methodology was also expanded to include arylation of phenols, giving diaryl ethers in good to excellent yields. In the second project, an arylation method that included a wider range of aliphatic alcohols was developed. The scope of accessible alkyl aryl ethers was studied and included a comparative study of phenylation and nitrophenylation of various alcohols. Finally, a formal metal-free synthesis of butoxycain was performed, illustrating the applicability of the developed method. The third project focused on the limitations and side reactions occurring in Chapter 2 and 3. First, an approach to access symmetric diaryl ethers via arylation of hydroxide was presented. This reaction gave rise to a number of side products, which we hypothesized to originate from aryne-type intermediates. A mechanism for the formation of these side products was suggested, supported by trapping and deuterium labeling experiments. Oxidation of the alcohol to the corresponding ketone was also observed and the mechanism of this interesting side reaction was investigated. The latter was suggested to proceed via an intramolecular oxidation without the involvement of radicals or arynes. The fourth project covers a method to synthesize highly sterically congested alkyl aryl ethers via arylation of tertiary alcohols using diaryliodonium salts. The method displayed a broad scope of tertiary alcohols and was also suitable for fluorinated alcohols. The final project detailed in this thesis deals with C-arylation with diaryliodonium salts, showcasing nitroalkanes as well as a nitro ester as suitable nucleophiles for metal-free arylation.At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 3: Manuscript.
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Seidl, Thomas Ludwig. "The Preparation of Diaryliodonium Salts for Application in Arylation Chemistry." PDXScholar, 2018. https://pdxscholar.library.pdx.edu/open_access_etds/4238.
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Diaryliodonium salts offer potential as novel reagents for arylation chemistry. An overall goal and successful outcome of this work has been to further understanding of diaryliodonium salt chemistry by developing practical methods that enable chemists more convenient access to these reagents, for the purpose of reaction development. To this end a robust and convenient preparation method has been developed and resulted in novel commercially available diaryliodonium salts. The remainder of the work described, has focused on understanding the parameters important to diaryliodonium mediated arylation and has resulted in a solid framework that multiple future development efforts can build upon.
A strategy adopted throughout this work was to use multivariate methodologies such as Design of Experiments (DoE). Applicable chapters show the results of optimization studies that were carried out using DoE, during the course of this work. Additionally, the desire to further realize the potential that DoE has to offer inspired of a search for parameters to study fundamental reactivity. Chapter 2 details the development of a practical diaryliodonium salt synthesis that is convenient, facile, and economical. A detailed procedure is also included and was drafted to the requirements for publication in the journal Organic Synthesis. Finally, limitations and future directions of the method are discussed. Chapter 3 describes studies aimed at understanding the role of the counter anion; a very practical counter anion screening method is presented. Future directions are discussed and include detailed characterization of diaryliodonium salts by NMR. Chapter 3 also describes a practical, scalable, and rapid salt exchange method developed during this work. Chapter 4 describes the results obtained in studying an azidation reaction via solubility parameters. All Supporting Information, including characterization data and experimental details, are provided in Chapter 5.
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Malmgren, Joel. "Iodonium Salts : Preparation, Chemoselectivity and Metal-Catalyzed Applications." Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2014. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-107694.
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This thesis concerns the preparation and use of diaryliodonium salts. In Project I various unsymmetrical diaryliodonium salts were reacted with three different nucleophiles in order to study the chemoselectivity of the reactions of the salts. The main focus of this project was to gain a deeper understanding of the underlying factors that affect the chemoselectivity in transition metal-free arylation reactions. They were found to be very nucleophile-dependent. Some nucleophiles were very sensitive to electronic effects, whereas others were sensitive to steric factors. Ultimately, some arenes are never transferred. A very interesting scrambling reaction was also observed under the reaction conditions, where unsymmetrical diaryliodonium salts form symmetrical salts in situ. Project II details the preparation of N-heteroaryliodonium salts via a one-pot procedure. The salts were designed so that the N-heteroaryl moiety was selectively transferred in applications both with and without transition metals. The chemoselectivity was demonstrated by selective transfer of the pyridyl group onto two different nucleophiles. The third project in the thesis discusses the synthesis of alkynyl(aryl)iodonium salts and alkynylbenziodoxolones from arylsilanes. This protocol could potentially be a very useful complement to the existing procedures, in which boronic acids are used. The last part of the thesis (Project IV) describes a C-2 selective arylation of indoles where diaryliodonium salts were used in combination with hetero-geneous palladium catalysis. This transformation was performed in water at ambient temperature to 50 °C, and tolerated variations of both the indole and the diaryliodonium salt. Importantly, several N-H indoles could be arylated. The MCF-supported Pd-catalyst showed very little leaching and it was demonstrated that the main part of the reaction occurred via heterogeneous catalysis.At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 3: Manuscript. Paper 4: Accepted.
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Kolay, Merve. "Dibenzophenazine And Quinoxaline Derivatives As Novel Visible Photosensitizers For Diaryliodonium Salts." Master's thesis, METU, 2011. http://etd.lib.metu.edu.tr/upload/12613419/index.pdf.
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This study is focused on the use of visible light in photoinitiated cationic polymerization. Photoinitiated polymerization of oxiranes, vinyl ethers, and other vinyl monomers was achieved. In doing so, (2-(2,3 dihydrobenzo [b][1,4]dioxin-6-yl)-3-(2,3-dihydrobenzo[b]-[1,4]dioxin-7-yl)-5-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-8-(2,3-dihydrothieno[3,4-b][1,4]dioxin-7yl) quinoxaline) (DBQEd) and poly(2,3,5,8-tetra(thiophen-2-yl)quinoxaline) (TTQ), two dibenzo[a,c]phenazine derivatives10,13-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)dibenzo[a,c] phenazine (PHED) and 10,13-bis(4-hexylthiophen-2-yl)dibenzo[a,c]phenazine (PHEHT) were utilized as the photosensitizers for diaryliodonium salt photoinitiators. Novel dyes based on the dibenzo[a,c]phenazine and quinoxaline skeleton were shown to be efficient in carrying out the cationic photopolymerizations of a wide variety of epoxide, oxetane, and vinyl monomers at room temperature upon irradiation with long-wavelength UV and visible light. The polymerizations were initiated at room temperature in the presence of diphenyliodonium hexafluorophosphate (Ph2I+PF-6) and monitored by optical pyrometry (OP). The photopolymerization of an epoxide monomer via solar irradiation was also demonstrated.
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Bielawski, Marcin. "Diaryliodonium Salts : Development of Synthetic Methodologies and α-Arylation of Enolates." Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2011. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-54738.
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This thesis describes novel reaction protocols for the synthesis of diaryliodonium salts and also provides an insight to the mechanism of α-arylation of carbonyl compounds with diaryliodonium salts. The first chapter gives a general introduction to the field of hypervalent iodine chemistry, mainly focusing on recent developments and applications of diaryliodonium salts. Chapter two describes the synthesis of electron-rich to electron-poor diaryliodonium triflates, in moderate to excellent yields from a range of arenes and iodoarenes. In chapter three, it is described that molecular iodine can be used together with arenes in a direct one-pot, three-step synthesis of symmetric diaryliodonium triflates. A large scale synthesis of bis(4-tert-butylphenyl)iodonium triflate is also described, controlled and verified by an external research group, further demonstrating the reliability of this methodology. The fourth chapter describes the development of a sequential one-pot synthesis of diaryliodonium salts from aryl iodides and boronic acids, furnishing symmetric and unsymmetric, electron-rich to electron-poor diaryliodonium tetrafluoroborates in moderate to excellent yields. This method was developed to overcome the regiochemical limitations imposed by the reaction mechanism in the protocols described in the preceding chapters. Chapter five describes a one-pot synthesis of heteroaromatic iodonium salts under similar conditions described in chapter two. The final chapter describes the reaction of enolates with chiral diaryliodonium salts or together with a phase transfer catalyst yielding racemic products. DFT calculations were performed, which revealed a low lying energy transition state (TS) between intermediates, which is believed to be responsible for the lack of selectivity observed in the experimental work. It is also proposed that a [2,3] rearrangement is preferred over a [1,2] rearrangement in the α-arylation of carbonyl compounds. The synthetic methodology described in this thesis is the most generally applicable, efficient and high-yielding to date for the synthesis of diaryliodonium salts, making these reagents readily available for various applications in synthesis.
10
Sundalam, Sunil Kumar. "The Discovery and Development of Metal-Free Arylation Reactions with Unsymmetrical Diaryliodonium Salts." PDXScholar, 2017. https://pdxscholar.library.pdx.edu/open_access_etds/3764.
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Functionalizing arenes and heteroarenes has been an active area of research since the 19th century, due to the presence of these molecular structures in many industrially important sectors. A tremendous amount of research has been published in achieving these chemical transformations using stoichiometric reagents and transition metal-catalyzed reactions. However, challenges still remain. An alternative and comparable methodology to metal-catalyzed reactions to overcome the drawbacks will advance this particular area of research is desirable.
Hypervalent iodine compounds offer a promising approach to metal-free arylation reactions. These mild, air and moisture stable compounds have showed significant success as non-toxic and metal-free reagents for the arylation reactions. In particular, unsymmetrical diaryliodonium salts offer functionalization of complex arene structure in an efficient and sustainable pathway.
A base-mediated coupling reaction for the metal-free synthesis of alkyl-aryl ethers by using unsymmetrical diaryliodonium salts and aliphatic alcohols is described. This method shows broad substrate scope with respect to both of the coupling partners to produce industrially useful alkyl-aryl ethers in moderate to excellent yields. The reaction is operationally simple, proceeds at mild temperature, and is atom-economical. Sustainability and synthetic utility of this reaction is demonstrated by the use of unsymmetrical aryl(mesityl)iodonium salts as the arylating agents. A limitation of poor reactivity of electron rich unsymmetrical diaryliodonium salts was overcome by designing 2nd generation conditions and using trimethoxy benzene (TMP) as the auxiliary group.
Additionally discovery and development of an efficient method to access highly functionalized arynes from unsymmetrical aryl(mesityl)iodonium tosylate salts is presented. The aryne intermediates are generated by ortho C-H deprotonation of aryl(mesityl)iodonium salt with an amide base and subsequently trapped in a cycloaddition reaction with furan in moderate to good yields. Selective iodonium moiety elimination is discussed and the effect of auxiliary and temperature to reduce the regioisomeric ratio is demonstrated. Finally, additional coupling partner including benzyl azide and aliphatic amines are presented to show further utility of this methodology. Also, mechanistic investigations leading to the moderate reactivity of some electron rich unsymmetrical diaryliodonium salts is discussed.
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Jayatissa, Kuruppu Lilanthi. "A Metal-Free Approach to Biaryl Compounds: Carbon-Carbon Bond Formation from Diaryliodonium Salts and Aryl Triolborates." PDXScholar, 2015. https://pdxscholar.library.pdx.edu/open_access_etds/2229.
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Biaryl moieties are important structural motifs in many industries, including pharmaceutical, agrochemical, energy and technology. The development of novel and efficient methods to synthesize these carbon-carbon bonds is at the forefront of synthetic methodology. Since Ullmann’s first report of stoichiometric Cu-mediated homo-coupling of aryl halides, there has been a dramatic evolution in transition metal catalyzed biaryl cross-coupling reactions.
Our work focuses on the discovery and development of an unprecedented reagent combination for metal-free cross-coupling. It is hypothesized that direct carbon-carbon bond formation occurs via a triaryl-λ3-iodane and that electrophile/nucleophile pairing is critical for success in the reaction. Proof-of-concept for this approach focused on the reaction between bromo 4-trifluoromethylphenyl (trimethoxybenzene)-λ3-iodane and potassium 3-fluorophenyltriolborate. The spectator ligand and counter ions are important parameters for both reactivity and selectivity of the aryl group transfer in this reaction. Moderate to good yields of biaryl products are obtained by this method. Experimental evidence supports the assertion of a metal-free cross-coupling reaction.
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Racicot, Léanne. "Extending the boundaries of diaryliodonium reagents : expressing I-nucleophilicity of aryl iodides and metal-free preparation of sulfonium salts." Thesis, University of British Columbia, 2016. http://hdl.handle.net/2429/59346.
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Diaryliodonium salts are a well-established class of hypervalent iodine reagents and act as aryl group transfer agents towards nucleophiles. This work established the possibility of metathesis between diaryliodonium triflates and various iodoarenes. In an effort to further understand the factors that govern this process, λ³-iodanes containing 2-thienyl moieties were prepared. As a result, aryl iodides unable to undergo metatesis previously were found to be suitable nucleophiles as the metathesis favors diaryliodonium species where more nucleofugal aryl iodides, such as 2-iodothiophene, are expelled during the course of the reaction. In addition, we showed that copper catalysis was not necessary for the arylation of sulfides, selenides and tellurides. Indeed, thermal reactions between the chalcogenides and diaryliodonium triflates afforded the corresponding triarylchalcogenium salts in good yields. This is particularly significant for the preparation of the triaryltelluronium species, as only limited protocols for their preparation were known.Science, Faculty of
Chemistry, Department of
Graduate
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Bhatt, Satwinder Singh. "Diaryliodonium salts as precursors to electron-rich [¹⁸F]fluoroarenes for use in the medical imaging technique, Positron Emission Tomography." Thesis, University of Newcastle upon Tyne, 2016. http://hdl.handle.net/10443/3262.
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Stridfeldt, Elin. "Hypervalent Iodine Reagents in Metal-Free Arylations and Vinylations : Investigation of Suitable Coupling Partners and Synthesis of New Reagents." Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2017. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-141580.
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This thesis concerns the development of metal-free reactions to obtain carbon-heteroatom and carbon-carbon bonds. This is achieved by transferring carbon ligands from hypervalent iodine reagents to suitable nucleophiles. The bulk of the work presented herein concerns arylation of oxygen and nitrogen nucleophiles, using the well-known diaryliodonium salts as aryl sources. In the first project, O-arylation of the oxime ethyl acetohydroxamate was studied. It was found that electron-poor as well as electron-rich aryl moieties could be transferred successfully to this nucleophile. Furthermore, the protocol could be extended to a sequential one-pot synthesis of benzo[b]furans. This method allowed for a fast synthesis of the natural product stemofuran A and formal syntheses of other natural products. In a successive project, O-arylation of hydroxide and aliphatic alkoxides was investigated. It is known that electron-poor aryl moieties can be transferred to these nucleophiles in moderate to high yields. However, combined with more electron-rich diaryliodonium salts, a large amount of side products were formed. These were suppressed upon addition of aryne traps, suggesting that aryne pathways are competing with the desired ligand coupling. It was also observed that secondary alcohols were oxidized to the corresponding ketones. The mechanism for this oxidation was investigated and aryne pathways could be excluded. Instead we suggest that the carbinol hydrogen gets deprotonated via an internal mechanism, after the alkoxide has coordinated to the iodonium salt. Highly sterically congested alkyl aryl ethers could be obtained in high yields by combining tertiary alcohols with ortho-blocked diaryliodonium salts. Next, N-arylation of secondary acyclic amides was studied using acetanilide as the model substrate. This procedure was suitable for transfer of electron-poor as well as ortho-substituted aryl moieties, but attempts to transfer very electron-rich aryl groups were unsuccessful. On the other hand, the amides displayed a complementary reactivity, allowing phenylation of electron-rich amides. In the final project, a one-pot synthesis of the cyclic iodonium reagent vinylbenziodoxolone is presented. These compounds have not been explored as reagents earlier. Initial screenings showed that the vinyl moiety could be transferred to nitrocyclohexane with opposite regioselectivity compared to the acyclic analogue of the reagent.At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 2: Manuscript.
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Yilmaz, Seda. "Long Wavelength Photosensitizers With Benzotriazole And Benzimidazole Skeletons For Cationic Polymerization." Master's thesis, METU, 2011. http://etd.lib.metu.edu.tr/upload/12613457/index.pdf.
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Benzimidazole and benzotriazole derivatives, 4-(2,3-Dihydrothieno[3,4-b][1,4]
dioxin-5-yl)-7-(2,3-dihydrothieno[3,4b][1,4]dioxin-7-yl)-2-benzyl-1H-benzo[d]
imidazole (BIm-Ed), 2-benzyl-4,7-di(thiophen-2-yl)-2H-benzo[d] [1,2,3] triazole
(BBTS), and 2-benzyl-4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-2Hbenzo[
d] [1,2,3] triazole (BBTES) were employed as photosensitizers for
diaryliodonium salt photoinitiators in cationic photopolymerization of various
epoxide and vinyl ether monomers. Diphenyliodonium hexafluorophosphate
(Ph2I+PF6¯) salt was used as the photoinitiator in this study. Extended conjugation and electron-rich moieties of the photosensitizers enabled the use of long wavelength UV and visible light emitting light sources in cationic photopolymerizations. Polymerizations were achieved at room temperature and monitored by optical pyrometry. Photopolymerization of a diepoxide monomer with ambient solar irradiation was examined.
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Jalalian, Nazli. "Development and Applications of Hypervalent Iodine Compounds : Powerful Arylation and Oxidation Reagents." Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2012. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-75810.
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The first part of this thesis describes the efficient synthesis of several hypervalent iodine(III) compounds. Electron-rich diaryliodonium salts have been synthesized in a one-pot procedure, employing mCPBA as the oxidant. Both symmetric and unsymmetric diaryliodonium tosylates can be isolated in high yields. An in situ anion exchange also enables the synthesis of previously unobtainable diaryliodonium triflates. A large-scale protocol for the synthesis of a derivative of Koser’s reagent, that is an isolable intermediate in the diaryliodonium tosylate synthesis, is furthermore described. The large-scale synthesis is performed in neat TFE, which can be recovered and recycled. This is very desirable from an environmental point of view. One of the few described syntheses of enantiopure diaryliodonium salts is discussed. Three different enantiopure diaryliodonium salts bearing electron-rich substituents are synthesized in moderate to high yields. The synthesis of these three salts shows the challenge in the preparation of electron-rich substituted unsymmetric salts. The second part of the thesis describes the application of both symmetric and unsymmetric diaryliodonium salts in organic synthesis. A metal-free efficient and fast method for the synthesis of diaryl ethers from diaryliodonium salts has been developed. The substrate scope is wide as both the phenol and the diaryliodonium salt can be varied. Products such as halogenated ethers, ortho-substituted ethers and bulky ethers, that are difficult to obtain with metal-catalyzed procedures, are readily prepared. The mild protocol allows arylation of racemization-prone a-amino acid derivatives without loss of enantiomeric excess. A chemoselectivity investigation was conducted, in which unsymmetric diaryliodonium salts were employed in the arylation of three different nucleophiles in order to understand the different factors that influence which aryl moiety that is transferred to the nucleophile.At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 2: Accepted. Paper 5: Submitted. Paper 6: Manuscript.