Relevant bibliographies by topics / Arylation

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  1. Journal articles
  2. Dissertations / Theses
  3. Books
  4. Book chapters
  5. Conference papers
  6. Reports

Academic literature on the topic 'Arylation'

Author: Grafiati
Published: 4 June 2021
Last updated: 19 April 2025

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Journal articles on the topic "Arylation"

1

Rossi, Renzo, and Maurizio Ciofalo. "Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art." Current Organic Chemistry 26, no. 3 (February 2022): 215–74. http://dx.doi.org/10.2174/1385272826666220201124008.

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Abstract: This unprecedented review with 322 references provides a critical up-to-date picture of the Pd-catalysed intermolecular direct C–H bond arylation of heteroarenes with arylating reagents alternative to aryl halides that include aryl sulfonates (aryl triflates, tosylates, mesylates, and imidazole-1-sulfonates), diaryliodonium salts, [(diacetoxy)iodo]arenes, arenediazonium salts, 1-aryltriazenes, arylhydrazines and N’-arylhydrazides, arenesulfonyl chlorides, sodium arenesulfinates, arenesulfinic acids, and arenesulfonohydrazides. Particular attention has been paid to summarise the preparation of the various arylating reagents and to highlight the practicality, versatility, and limitations of the various developed arylation protocols, also comparing their results with those achieved in analogous Pd-catalysed arylation reactions involving the use of aryl halides as electrophiles. Mechanistic proposals have also been briefly summarised and discussed. However, data concerning Pd-catalysed direct C–H bond arylations involving the C–H bonds of aryl substituents of the examined heteroarene derivatives have not been taken into account.
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Čorić, Ilija, and Jyoti Dhankhar. "Introduction to Spatial Anion Control for Direct C–H Arylation." Synlett 33, no. 06 (February 1, 2022): 503–12. http://dx.doi.org/10.1055/s-0040-1719860.

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AbstractC–H activation of functionally rich molecules without the need for directing groups promises shorter organic syntheses and late-stage diversification of molecules for drug discovery. We highlight recent examples of palladium-catalyzed nondirected functionalization of C–H bonds in arenes as limiting substrates with a focus on the development of the concept of spatial anion control for direct C–H arylation.1 C–H Activation and the CMD Mechanism2 Nondirected C–H Functionalizations of Arenes as Limiting Substrates3 Nondirected C–H Arylation4 Spatial Anion Control for Direct C–H Arylation5 Coordination Chemistry with Spatial Anion Control6 Conclusion
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Kalyani, Dipannita. "Pd- and Ni-catalyzed C–H arylations using C–O electrophiles." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 315–19. http://dx.doi.org/10.1515/pac-2014-5033.

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Abstract This manuscript describes the development of Pd- and Ni-catalyzed arylations of unactivated arene C–H bonds using C–O electrophiles. A method for Pd-catalyzed intramolecular C–H arylation is accomplished using inexpensive and readily available tosylates and mesylates as electrophiles. This transformation is efficient for the synthesis of various heterocyclic motifs including furans, carbazoles, indoles, and lactams. Additionally, a protocol for a one-pot sequential tosylation/arylation of phenol derivatives is presented. The use of earth-abundant and inexpensive Ni catalysts for an intramolecular C–H arylation using aryl pivalates as electrophiles is described. Preliminary mechanistic studies for both the Pd- and Ni-catalyzed arylations are discussed.
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Bellina, Fabio. "Real Metal-Free C–H Arylation of (Hetero)arenes: The Radical Way." Synthesis 53, no. 15 (March 15, 2021): 2517–44. http://dx.doi.org/10.1055/a-1437-9761.

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AbstractSynthetic methodologies involving the formation of carbon–carbon bonds from carbon–hydrogen bonds are of significant synthetic interest, both for efficiency in terms of atom economy and for their undeniable usefulness in late-stage functionalization approaches. Combining these aspects with being metal-free, the radical C–H intermolecular arylation procedures covered by this review represent both powerful and green methods for the synthesis of (hetero)biaryl systems.1 Introduction2 Arylation with Arenediazonium Salts and Related Derivatives2.1 Ascorbic Acid as the Reductant2.2 Hydrazines as Reductants2.3 Gallic Acid as the Reductant2.4. Polyanilines as Reductants2.5 Chlorpromazine Hydrochloride as the Reductant2.6 Phenalenyl-Based Radicals as Reductants2.7 Electrolytic Reduction of Diazonium Salts2.8 Visible-Light-Mediated Arylation3 Arylation with Arylhydrazines: Generation of Aryl Radicals Using an Oxidant4 Arylation with Diaryliodonium Salts5 Arylation with Aryl Halides6 Conclusions
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Abdelmalek, Fatiha, Fazia Derridj, Safia Djebbar, Jean-François Soulé, and Henri Doucet. "Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp2)–H bond arylations." Beilstein Journal of Organic Chemistry 11 (October 28, 2015): 2012–20. http://dx.doi.org/10.3762/bjoc.11.218.

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We report herein a two or three step synthesis of fluorinated π-conjugated oligomers through iterative C–H bond arylations. Palladium-catalyzed desulfitative arylation of heteroarenes allowed in a first step the synthesis of fluoroaryl-heteroarene units in high yields. Then, the next steps involve direct arylation with aryl bromides catalyzed by PdCl(C3H5)(dppb) to afford triad or tetrad heteroaromatic compounds via regioselective activation of C(sp2)–H bonds.
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Luo, Anping, Min Zhang, Zhangyi Fu, Jingbo Lan, Di Wu, and Jingsong You. "Copper-catalyzed remote C–H arylation of polycyclic aromatic hydrocarbons (PAHs)." Beilstein Journal of Organic Chemistry 16 (March 30, 2020): 530–36. http://dx.doi.org/10.3762/bjoc.16.49.

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The regioselective C–H arylation of substituted polycyclic aromatic hydrocarbons (PAHs) is a desired but challenging task. A copper-catalyzed C7–H arylation of 1-naphthamides has been developed by using aryliodonium salts as arylating reagents. This protocol does not need to use precious metal catalysts and tolerates wide variety of functional groups. Under standard conditions, the remote C–H arylation of other PAHs including phenanthrene-9-carboxamide, pyrene-1-carboxamide and fluoranthene-3-carboxamide has also accomplished, which provides an opportunity for the development of diverse organic optoelectronic materials.
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Diesendruck, Charles, and Shlomy Arava. "Strategies for the Synthesis of N-Arylammonium Salts." Synthesis 49, no. 16 (June 26, 2017): 3535–45. http://dx.doi.org/10.1055/s-0036-1588868.

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The N-arylation of tertiary amines to provide sp3 quaternary ammonium salts is a challenge in organic chemistry. To date, no general method for such arylations has been established. Here, we summarize a variety of strategies that have been tested, starting with harsh nucleophilic aromatic substitutions, through to the use of copper catalysis and the application of strong electrophiles, such as phenyl cations and benzynes. The achievements and limitations of each method are summarized, and the challenges yet to be met in the synthesis of charged ammonium compounds are described.1 Introduction2 Alkylation of Anilines: The Menshutkin Reaction3 Arylations3.1 Nucleophilic Aromatic Substitutions by Tertiary Amines3.2 Preparation of N-Arylpyridinum Salts from Zincke and Pyrylium Salts3.3 Arylations Using Phenyl Cations3.4 Copper-Catalyzed Arylation of N-Heteroarenes3.5 Benzynes as Aryl Electrophiles4 Conclusions and Perspective
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Huang, Qing, Liangxian Liu, Jiayi Zhu, Yu Chen, Feng Lin, and Baoshuang Wang. "Highly Regioselective Arylation of 1,2,3-Triazole N-Oxides with Sodium Arenesulfinates via Palladium-Catalyzed Desulfitative Cross-Coupling Reaction." Synlett 26, no. 08 (March 5, 2015): 1124–30. http://dx.doi.org/10.1055/s-0034-1380186.

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A convenient and highly regioselective palladium-catalyzed direct C5-arylation of 1,2,3-triazole N-oxides was developed in the presence of silver carbonate and tripotassium phosphate. This protocol allowed use of sodium arylsulfinates, diphenylphosphine oxide, and triphenylphosphine as arylating reagents to produce 2-aryl-5-aryl-1,2,3-triazole N-oxides in good to excellent yields, providing a complement to the existing methods for the direct arylation of 1,2,3-triazole N-oxides.
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Du, Zhengyin, Hua Feng, Fangli Gang, Yang Che, and Ying Fu. "Palladium-Catalyzed Regioselective C-5 Arylation of 1,2,3-Triazoles with Diaryliodonium Salts." Synlett 28, no. 13 (May 4, 2017): 1624–29. http://dx.doi.org/10.1055/s-0036-1588815.

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An effective method for C-5 arylation of 1,4-disubstituted 1,2,3-triazoles and C-5 regioselective arylation of 1-substituted 1,2,3-triazoles via sp2 C–H activation with palladium as a catalyst and diaryliodonium salts as arylating reagents is described. Various electron-rich and electron-deficient substituents attached to triazoles and diaryliodonium salts were tolerable to give the desired products with good isolated yields in 24 hours under air atmosphere.
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Dodonova, Jelena, and Sigitas Tumkevicius. "Fused Pyrrolo[2,3-d]pyrimidines (7-Deazapurines) by Palladium-Catalyzed Direct N–H and C–H Arylation Reactions." Synthesis 49, no. 11 (March 2, 2017): 2523–34. http://dx.doi.org/10.1055/s-0036-1588734.

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Palladium-catalyzed intramolecular direct C–H arylations for the synthesis of hitherto unknown fused hetero systems containing an incorporated pyrrolo[2,3-d]pyrimidine scaffold are described. Pyrimido[5′,4′:4,5]pyrrolo[2,1-a]isoindoles were synthesized from 2,4-di­arylpyrrolo[2,3-d]pyrimidines and o-bromobenzyl bromides by using a cascade N-benzylation/C–H arylation reaction sequence. A series of pyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines were successfully assembled via a domino process involving the palladium-catalyzed direct double C–H arylation reactions of 2,4,7-triarylpyrrolo[2,3-d]pyrimidines with o-bromoiodobenzenes.
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Dissertations / Theses on the topic "Arylation"

1

Zhang, Chi Ph D. Massachusetts Institute of Technology Department of Chemistry. "Cysteine arylation." Thesis, Massachusetts Institute of Technology, 2017. http://hdl.handle.net/1721.1/112448.

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Thesis: Ph. D., Massachusetts Institute of Technology, Department of Chemistry, 2017.
Cataloged from PDF version of thesis.
Includes bibliographical references.
Proteins are the chemical and biological foundation of life. The longstanding goals of chemical biology are to understand the structure and function of proteins and to use these biomolecules for applications in chemistry, biology, medicine, and material science. To achieve such goals, highly efficient, selective, and robust chemical reactions are desired to modify proteins. For decades, cysteine-based reactions with maleimides and alkyl halides are the primary methods for selectively tagging proteins with fluorescent dyes, affinity and radio labels, drug molecules, and polymers and nanocomposites. These traditional reactions generate sulfur-sp³ carbon bonds between the cysteine thiol and the labeling reagents. The goal of this thesis is to develop new cysteine arylation reactions to generate sulfur-sp² carbon bonds on proteins. These reactions are used to make novel peptide and protein therapeutics. Two mechanistically complementary approaches are developed to arylate cysteine thiol. First, through a nucleophilic aromatic substitution (SNAr) mechanism, fluorinated aromatic reagents are used for the regioselective arylation of a single cysteine in the presence of many. An enzyme-tag pair (glutathione S-transferase (GST) and glutathione (GSH)) and a self-labeling short peptide (Phe-Cys-Pro-Phe, the 7-clamp) are respectively developed to recognize the fluorinated aromatic reagents and to promote the arylation reaction in aqueous solution. The second approach utilizes organometallic palladium reagents to chemoselectively install electron-neutral and electron-rich aryls on cysteine thiols. These cysteine arylation reactions are applied to the synthesis of macrocyclic peptides and antibody-drug conjugates (ADCs). Long unprotected macrocyclic peptides up to forty residues are efficiently synthesized using the GST enzyme. Using bispalladium reagents, macrocyclic peptides bearing aryl linkers are synthesized via crosslinking of two cysteine thiols. [pi]-Clamp antibodies enable a one-step synthesis of site-specific antibody-drug conjugates to selectively kill cancer cells. Organometallic palladium reagents are used to synthesize linker-free ADCs where the drug molecules are directly linked to cysteine thiols in antibodies.
by Chi Zhang.
Ph. D.
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Corrie, Thomas James Alexander. "Intramolecular direct arylation." Thesis, University of Edinburgh, 2017. http://hdl.handle.net/1842/28820.

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The research conducted for this thesis has led to the development of an intramolecular gold-catalysed direct arylation protocol whereby tethered arenes and aryltrimethylsilanes are coupled (Scheme 1). In Chapter 1, the key synthetic and mechanistic studies that have ultimately led to the conception of this project are introduced. In Chapter 2, the substrate scope of intramolecular direct arylation is assessed. The reaction tolerates a wide range of substrates with tether lengths between one and five units (containing C, N and O) generating 5- to 9- membered rings. Substrates that lead to 5-membered rings (1 → 2) can tolerate a broad electronic range of substituents and proceed under the mildest reaction conditions (≤ 1 mol% catalyst, room temperature) and with excellent yields. A smaller collection of examples is demonstrated for the cyclisation to 6- and 7- membered rings (3 → 4, 5 → 6), but no heating is required and good yields are maintained throughout the series. The synthetically challenging synthesis of 8- and 9- membered rings (7 → 8, 9 → 10) is successful, albeit with slightly more forcing conditions (4 mol%, up to 50 °C). The methodology was subsequently applied in the successful 10-step synthesis of natural product allocolchicine 11. In Chapter 3, the operative reaction mechanism is elucidated. Reaction monitoring techniques allowed for the detailed study of linear free energy relationships (LFERs) and kinetic isotope effects (KIEs), which in turn allowed for deduction of the reaction turnover-limiting step (TLS) and thus the first quantitative experimental data on the effects of aryl electron demand and conformational freedom on the rate of reductive elimination from diarylgold(III) species. The mechanistic investigation led to the observation of complex kinetic profiles for specific substrates. The origin of these unusual effects is the focus of Chapter 4. By combining experiment with kinetic simulation, an off-cycle catalyst inhibition pathway was identified and the understanding of this process allowed for a re-optimisation of reaction conditions. In Chapter 5, the general kinetic parameters that could govern any domino reaction combining inter- and intramolecular direct arylation are deduced through kinetic analysis and simulation of hypothetical systems. The results of the kinetic analysis were proved experimentally through the successful combination of intra- and intermolecular gold-catalysed direct arylation. The products of intramolecular cyclisation 2, generated in-situ, are demonstrated to couple with intermolecular aryltrimethylsilanes 12, resulting in a rapid increase in molecular complexity from simple substrates in one pot.
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Turner, Gemma L. "Direct arylation of thiazoles." Thesis, University of Edinburgh, 2009. http://hdl.handle.net/1842/3188.

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An introduction to the thiazole ring system is presented together with a detailed, but non-exhaustive review of the rapidly emerging area of palladium-mediated directed arylation. The direct arylation of thiazole is also discussed together with our attempts to improve the established methods. A high-yielding, mild protocol has been developed for the functionalisation of the most electron-rich carbon-hydrogen bonds in a number of heterocyclic ring systems, this represents the first example of a C-H activation reaction being accomplished in aqueous media and allows access to a diverse range of functionalised aryl heterocycles. In addition, work towards functionalisation of the thiazole C4 position is described. A number of different approaches are discussed and our endeavors are recorded.
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Evans, Ethan Daniel. "Long peptides for cysteine arylation." Thesis, Massachusetts Institute of Technology, 2018. http://hdl.handle.net/1721.1/118258.

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Thesis: Ph. D. in Biological Chemistry, Massachusetts Institute of Technology, Department of Chemistry, 2018.
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Biological reactivity is typically carried out by large enzymes. There are few examples of reactive, amino-acid-based polymers shorter than 100 residues in length. Of those that do exist, the majority are very short tags (<15 amino acids). Here, we attempted to first discover peptides roughly 30 amino acids in length that promote a nucleophilic aromatic substitution reaction and then understand the features and properties that emerge. Using the 20 canonical amino acids, there are 20³⁰ different peptide sequences possible in this size realm. To isolate a portion of the space capable of reacting with a perfluoroaromatic small molecule, we performed an mRNA display selection. This uncovered a host of putative reactive peptides with little similarity at the sequence level. The primary isolate (MP01) displayed reactivity confirming the success of the selection and was sensitive to truncation and denaturants. We next set out to study the reactivity of an expanded portion of the isolated peptides and look for shared structural or mechanistic themes. Analyzing an additional 26 peptides with almost no sequence similarity, we discovered diverse levels of reactivity along with sequences capable of undergoing multiple reactions. Using computational structure prediction and circular dichroism spectroscopy we discovered that both mixed alpha-helical and random coil as well as beta-sheet-based reactive peptides existed. Studying their structural properties revealed that many of the peptides undergo significant structural alterations upon reaction with the perfluoroaromatic. Returning to MP01 we studied its mutational tolerance as well as its structural and mechanistic properties. Alanine scanning mutagenesis revealed mutations that diminished reactivity in addition to others that improved its function. Computational structure prediction suggested a mixed helical and random coil structure. Combining the beneficial mutations with insights from modeling initiated an iterative process that ultimately led to a 100-fold improved reaction rate. This sequence (MP01-Gen4) was six mutations different from MPG 1 and was more reactive than any other peptide discovered. MP01-Gen4 displayed flexibility and lacked a defined three-dimensional structure, however, it was significantly more helical than its progenitor. This sequence also displayed structural alterations, becoming more helical in the presence of its small molecule reaction partner, when either covalently reacted or noncovalently interacting.
by Ethan Daniel Evans.
Ph. D. in Biological Chemistry
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5

Fournier, Anne. "Intramolecular arylation of lithiated carbamates." Thesis, University of Manchester, 2012. https://www.research.manchester.ac.uk/portal/en/theses/intramolecular-arylation-of-lithiated-carbamates(165caa71-c229-4db3-a2e3-a77b097e5ef9).html.

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This thesis describes research carried out on the synthesis of tertiary alcohols or derivatives by N to C aryl/vinyl migration in lithiated carbamates. Section II.1 describes the first enantioselective synthesis of the antihistamine agent clemastine, as its (S,S)-stereoisomer as an illustration of the methodology. It has been achieved by ether formation between a proline-derived chloroethylpyrrolidine and an enantiomerically enriched tertiary alcohol. The tertiary alcohol was formed from the carbamate derivative of alpha-methyl-p-chlorobenzyl alcohol by invertive aryl migration on lithiation. The (S,S)-stereochemistry of the product confirms the invertive nature of the rearrangement in contrast with related ureas. Modelling work to establish the origin of this stereodivergent behaviour is reported in Section II.2. This also reports in-situ IR experiments providing evidence of the mechanistic pathway of the rearrangement of an O-benzyl-N-aryl carbamate. The scope of the N to C aryl migration in other stabilised organolithiums is shown in section II.3. The rearrangement is now addressed in more systematic manner, thus allowing the alpha-arylation of O-allyl and O-propargylcarbamates (by alpha-deprotonation) and O-vinylcarbamates (by alpha-deprotonation) to be achieved in good yields but with poor stereoselectivity. Section II.4 goes on to show that enol carbamates derived from aromatic or alpha,beta-unsaturated compounds and bearing an N-aryl substituent undergo carbolithiation by nucleophilic attack at the alpha position of the enol double bond. The resulting carbamate-stabilised allylic, propargylic or benzylic organolithium rearranges with N to C migration of the N-aryl substitutent, creating a quaternary carbon alpha to O. The products may be easily hydrolysed to generate multiply branched tertiary alcohols in good to moderate yields in a one-pot tandem reaction. Finally, Section II.5 proves that the rearrangement in lithiated carbamates can be extended to N to C vinyl transfer.
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Sävmarker, Jonas. "Palladium-Catalyzed Carbonylation and Arylation Reactions." Doctoral thesis, Uppsala universitet, Avdelningen för organisk farmaceutisk kemi, 2012. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-167720.

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Palladium-catalyzed reactions have found widespread use in contemporary organic chemistry due to their impressive range of functional group tolerance and high chemo- and regioselectivity. The pioneering contributions to the development of the Pd-catalyzed C-C bond forming cross-coupling reaction were rewarded with the Nobel Prize in Chemistry in 2010. Today, this is a rapidly growing field, and the development of novel methods, as well as the theoretical understanding of the various processes involved are of immense importance for continued progress in this field. The aim of the work presented in this thesis was to develop novel palladium(0)- and palladium(II)-catalyzed reactions. The work involved in achieving this aim led to the development of a Mo(CO)6-mediated carbonylative Stille cross coupling reaction for the preparation of various deoxybenzoins. The protocol utilized convenient gas-free conditions to facilitate the carbonylative coupling of benzyl bromides and chlorides with aryl and heteroaryl stannanes. Mo(CO)6-assisted conditions were then used in the development of a general protocol suitable for the aminocarbonylation of aryl triflates. Both electron-poor and electron-rich triflates were coupled with primary, secondary and aryl amines. In addition, DMAP was found to be a beneficial additive when using sterically hindered or poorly nucleophilic amines. An efficient and convenient method for the synthesis of styrenes from arylboranes was developed, employing the relatively inexpensive vinyl acetate as the ethene source under Pd(II)-catalyzed conditions. The reaction mechanism was studied using ESI-MS, and a plausible catalytic cycle was proposed. A method for the oxidative Heck reaction employing aryltrifluoroborates and aryl MIDA boronates was also developed. Electron-rich and electron-poor olefins were regioselectively arylated under microwave-assisted conditions. Various arylboron species were identified in an ongoing reaction using ESI-MS.    Further investigations led to the development of a direct method for the synthesis of arylamidines from aryltrifluoroborates and cyanamides. Under Pd(II)-catalyzed conditions it was possible to insert the aryl into primary, secondary and tertiary cyanamides. Finally, a desulfitative method for the synthesis of aryl ketones was developed. A variety of aryl sulfinates were effectively inserted into alkyl- and aryl nitriles. The mechanism was further investigated using ESI-MS and a plausible catalytic cycle was proposed.
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Leblanc, Mélissa. "Synthèse d'allocolchicinoides via une arylation directe." Thesis, University of Ottawa (Canada), 2006. http://hdl.handle.net/10393/27264.

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Le motif biaryle tricyclique est un motif important en chimie médicinale et est présent dans une grande variété de produits naturels. Les chimistes ont développé au cours des années différentes méthodologies pour les synthétiser. La majorité des réactions impliquent l'utilisation d'un aryle fonctionnalisé par un organometallique et réagissant avec un halogénure d'aryle. Récemment, notre laboratoire rapportait une nouvelle procédure permettant de synthétiser des biaryles tricycliques d'une façon efficace et rapide. Cette nouvelle méthodologie est une réaction d'arylation directe catalysée par le palladium, par laquelle la partie organometallique a été remplacée par un hydrogène. Ainsi, un halogénure d'aryle peut maintenant réagir avec un aryle simple pour former le biaryle désiré. Cette réaction d'arylation directe a été récemment étendue à la formation de biaryles tricycliques contenant un cycle à sept membres. Elle peut s'effectuer à partir des chlorures ou des bromures d'aryles. Cette méthodologie a donc été employée dans la synthèse formelle de l'allocolchicine et d'un de ses analogues. Pour effectuer la réaction d'arylation directe d'une façon efficace, il a été détermine que la proportion ligand/palladium jouait un rôle primordial dans la quantité de produit hydrodéhalogène obtenue. De plus, le choix du ligand, par ses propriétés stériques et électroniques, a un impact sur le pourcentage de conversion obtenu lors de la cyclisation. Les ligands riches en électrons, tels que 2-(dicyclohexylphosphino)-2'- N,N-dimethylaminobiphenyle, sont les ligands qui ont fourni les meilleurs résultats. Par ailleurs, concernant la formation du centre chiral retrouvé dans l'allocolchicine, deux stratégies de synthèse ont été explorées, soit un couplage asymétrique direct et une réduction enantiosélective. Finalement, l'alcool chiral a été obtenu à l'aide d'une réduction enantiosélective d'une cétone via un réactif de bore, dérivé d'un mélange équimolaire de pinène et de 9-BBN.
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Douglas, Gayle Elizabeth. "Investigations into direct N-arylation reactions." Thesis, University of Leeds, 2018. http://etheses.whiterose.ac.uk/23026/.

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This thesis details investigations and the optimisation of N-arylation reactions using preciousmetal- free conditions. It is an important motif in several pharmaceutical and agrochemical molecules. In 1965 Bock et al described the use of concentrated sulfuric acid and acetic acid as the solvent in a modified version of the Hofmann-Lӧffler-Freytag to carry out direct amination of aromatics via N-haloamines.1 The first section looks at the UV irradiation chemistry where we utilised N-halo species which under photolytic conditions form the aminium radicals. Several examples of tetrahydroquinolines being synthesised in flow have been carried out. Investigations into amination of electron-deficient heterocycles such as pyridines were also investigated. Unfortunately, no N-arylation was observed under the various conditions trialled. Similar investigations have been carried out into the photolysis of N-chloroamides with varying degrees of chain length and position of the amide. Under neutral conditions in the presence of a Lewis acid some success in N-arylation reactions has been observed. In the second section the use of iron(II) salts has been investigated towards the N-arylation reaction via the aminium radial generated from the N-halo species. A variety of substrates containing electron-poor and electron-rich aromatic rings have been synthesised under these conditions. This methodology has been expanded to include an iron salt variant of the work with examples of intramolecular and intermolecular direct N-arylation described. Using our methodology some simple aromatics and the drug naproxen have now been aminated successfully. The use of hydroxylamines as alternative precursors to the aminium radical has also been investigated with some success in the synthesis of various substrates.
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Williamson, Alice Elizabeth. "Novel methods for catalytic asymmetric arylation." Thesis, University of Cambridge, 2012. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.610600.

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10

Niwa, Takashi. "Studies on Palladium-Catalyzed Benzylic Arylation." 京都大学 (Kyoto University), 2009. http://hdl.handle.net/2433/77959.

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Kyoto University (京都大学)
0048
新制・課程博士
博士(工学)
甲第14583号
工博第3051号
新制||工||1454(附属図書館)
26935
UT51-2009-D295
京都大学大学院工学研究科材料化学専攻
(主査)教授 大嶌 幸一郎, 教授 檜山 爲次郎, 教授 松原 誠二郎
学位規則第4条第1項該当
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Books on the topic "Arylation"

1

Burke, Anthony J., and Carolina Silva Marques, eds. Catalytic Arylation Methods. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2014. http://dx.doi.org/10.1002/9783527672707.

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library, Wiley online, ed. Modern arylation methods. Weinheim: Wiley-VCH, 2009.

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Molloy, David Joseph. Studies in the synthesis of lead mediated arylations. Dublin: University College Dublin, 1997.

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Ryan, Sarah M. Arylation studies on [Beta]-keto sulphones and related compounds. Dublin: University College Dublin, 1995.

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Jacques, Teresa. I : Catalytic Direct C-H Arylation of Pyrazoles. II: Toward Modulation of Neuroplasticity with Small Molecules. [New York, N.Y.?]: [publisher not identified], 2013.

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Naoto, Chatani, and Ackermann L, eds. Directed metallation. Berlin: Springer Verlag, 2007.

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Ackermann, Lutz, ed. Modern Arylation Methods. Wiley, 2009. http://dx.doi.org/10.1002/9783527627325.

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Ackermann, Lutz. Modern Arylation Methods. Wiley & Sons, Incorporated, John, 2009.

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Mahiou, Belaid. An evaluation of charge generation in hydrogen atom abstraction processes: The reaction of homoaryl and heteroarylmethanes with t ø-butoxy radical. 1986.

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Burke, Anthony J., and Carolina Silva Marques. Catalytic Arylation Methods: From the Academic Lab to Industrial Processes. Wiley & Sons, Incorporated, John, 2014.

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Book chapters on the topic "Arylation"

1

Li, Jie Jack. "Meerwein arylation." In Name Reactions, 253. Berlin, Heidelberg: Springer Berlin Heidelberg, 2003. http://dx.doi.org/10.1007/978-3-662-05336-2_187.

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Li, Jie Jack. "Meerwein arylation." In Name Reactions, 225. Berlin, Heidelberg: Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/978-3-662-04835-1_176.

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Olofsson, Berit. "Arylation with Diaryliodonium Salts." In Hypervalent Iodine Chemistry, 135–66. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/128_2015_661.

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Leclerc, Mario, and Serge Beaupré. "Direct (Hetero)arylation Polymerization." In Synthetic Methods for Conjugated Polymers and Carbon Materials, 131–58. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527695959.ch4.

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Marcia de Figueiredo, Renata, and Jean-Marc Campagne. "Organocatalyzed Asymmetric Arylation and Heteroarylation Reactions." In Comprehensive Enantioselective Organocatalysis, 1043–66. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527658862.ch35.

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Miura, Masahiro, and Tetsuya Satoh. "Arylation Reactions via C-H Bond Cleavage." In Topics in Organometallic Chemistry, 55–83. Berlin, Heidelberg: Springer Berlin Heidelberg, 2005. http://dx.doi.org/10.1007/b104129.

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Liao, L., Y. Zhang, and J. S. Yu. "20.5.1.7.16 Catalytic α-Arylation of Alkyl Alkanoates." In Knowledge Updates 2024/1. Stuttgart: Georg Thieme Verlag KG, 2024. https://doi.org/10.1055/sos-sd-120-00150.

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Abstractα-Aryl carboxylic esters are important motifs or precursors in a wide variety of drugs, bioactive natural products, and pharmacologically active compounds. This chapter is an update to enrich the original Science of Synthesis chapter dedicated to the synthesis of alkyl alkanoates “Synthesis with Retention of the Functional Group” (Section 20.5.1.7). The current review focuses on recent advances in the catalytic α-arylation of alkyl alkanoates, and describes methods for the synthesis of α-aryl carboxylic compounds reported in the period 2001–2022. Seven main approaches are introduced: α-arylations of alkyl esters or their enolates, α-arylations of Reformatsky reagents with aryl halides, α-arylations of silyl ketene acetals, α-arylations of α-halo esters, α-arylations of α-diazo esters, decarboxylative or deacetylative α-arylation of β-carbonyl esters, and reductive C—O bond arylation of oxalates derived from α-hydroxy esters.
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"Synthetic Methods for Primary Anilines." In Methods and Strategies for C–N Bond Formation Reactions, 145–221. Royal Society of Chemistry, 2023. http://dx.doi.org/10.1039/bk9781837672615-00145.

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Aryl amines have received significant interest because these compounds widely exist in the structural backbones of ligands, pharmaceuticals, agrochemicals, natural products, and functional materials. In N-arylation reactions, several types of organic electrophile coupling partners such as (pseudo)halides (Ullmann-type and Buchwald–Hartwig couplings) and boronic acids (Chan–Lam coupling) are popular. The main synthetic methods for the preparation of these compounds involving N-arylation utilize aryl halides. Progress has been made with the coupling of arylating reagents which are less expensive than aryl halides, providing both a cost-effective and more efficient reaction route. For example, the process of C–H bond activation/functionalization, a step-efficient and atom-economical transformation, has emerged as a powerful strategy in C–N bond-forming reactions. Moreover, a transition-metal-free method for the N-arylation of amines using an aryne intermediate has been developed. This chapter focuses on recent advances in chemo- and regioselective N-arylation (either on one N-center or on the exocyclic N-site of the ring) or the selective arylation of amino alcohols without additional protection/deprotection using arylating reagents. This chapter provides an overview of arylating reagents for N-arylation reactions found in both basic and applied chemical research. The substrate scope, limitations, reaction mechanism, and chemoselectivity, as well as related control strategies of these reactions, are discussed. To the best of our knowledge, there has been no book about introducing arylating reagents to develop more efficient and environmentally friendly cross-coupling methods for the N-arylation of amines. We believe this critical review will provide necessary background information on the N-arylation of amines.
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Stadlbauer, W. "Arylation." In Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms, 1. Georg Thieme Verlag KG, 2002. http://dx.doi.org/10.1055/sos-sd-012-00369.

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Tomé, A. C. "Arylation." In Five-Membered Hetarenes with Three or More Heteroatoms, 1. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-013-00790.

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Conference papers on the topic "Arylation"

1

Rampon, Daniel S., Ludger A. Wessjohann, and Paulo H. Schneider. "Palladium-Catalyzed Direct Arylation of Selenophene." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013915174110.

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Aksenov, A., I. Aksenova, I. Borodaev, and Yu Smushkevich. "Regioselectivity of Arylation of 2,3'-Biquinolyl Dianion." In The 1st International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 1997. http://dx.doi.org/10.3390/ecsoc-1-02025.

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Olofsson, Berit. "Metal-Free Arylation of Phenols and Carboxylic Acids." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0184-1.

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Carmona, Rafaela C., and Carlos Roque D. Correia. "Asymmetric Arylation of Indenes via Heck-Matsuda Reaction." In 15th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_201381992939.

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Kobryn, Lesya, Eugeniya Bila, Mykola Ganushchak, and Volodymyr Mizyuk. "Arylation of Unsaturated Compounds by 6-coumarinyldiazonium Salt." In The 9th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2005. http://dx.doi.org/10.3390/ecsoc-9-01471.

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Embaby, Ahmed M., Sanne Schoffelen, Christian Kofoed, Morten Meldal, and Frederik Diness. "Chemoselective arylation of amino acids, peptides and proteins." In 37th European Peptide Symposium, 2210. The European Peptide Society, 2024. http://dx.doi.org/10.17952/37eps.2024.p2210.

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Čerňa, Igor, and Michal Hocek. "Direct C–H arylation of purines and purine nucleosides." In XIVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2008. http://dx.doi.org/10.1135/css200810327.

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Linhua, Shen, and Olivier Monasson. "New electrochemical method for Arylation of Cysteine containing peptides." In 37th European Peptide Symposium, 1051. The European Peptide Society, 2024. http://dx.doi.org/10.17952/37eps.2024.p1051.

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Villemin, Didier, Arnaud Jullien, and Nathalie Bar. "On Novel Non-Organometallic Aryl Nucleophile in Palladium-Catalyzed Arylation." In ECSOC 2024, 97. Basel Switzerland: MDPI, 2025. https://doi.org/10.3390/ecsoc-28-20147.

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Soares, Liliana A., Helena D. de Salles, and Paulo H. Schneider. "Highly enantioselective arylation of aromatic aldehydes, promoted by chiral phosphinite ligands." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0018-1.

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Reports on the topic "Arylation"

1

Seidl, Thomas. The Preparation of Diaryliodonium Salts for Application in Arylation Chemistry. Portland State University Library, January 2000. http://dx.doi.org/10.15760/etd.6122.

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Sundalam, Sunil. The Discovery and Development of Metal-Free Arylation Reactions with Unsymmetrical Diaryliodonium Salts. Portland State University Library, January 2000. http://dx.doi.org/10.15760/etd.5648.

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